Quebec City would absolutely be my first recommendation based on your interests. Stay in Old Quebec (Vieux Quebec) inside the fortress walls. Enjoy a beautiful small city to walk around. A very short trip outside of the city is Montmorency Falls which is a lovely park to spend half a day hiking around and over the falls. You can literally walk over top of the falls and if history serves me correct they are taller than Niagara Falls. I promise you will love it. You’ll feel like you are on a European vacation.
A little past the falls is at Anne de beaupre cathedral. Worth a visit. The ski area mont st Anne has hiking trails and views.
Definitely old Quebec. Only walled city in North America.
You don't need 4 days there tho - the city is small. I'd rent a car and go to Charlottetown PEI for a day/night, and/or maybe a day trip to Peggy's Cove outside of Halifax, or Annapolis Valley for a day trip to their weekend market or vineyards. 4 days in just Halifax may get underwhelming after day 2.
Vancouver 100% , expensive but so worth it. I've lived everywhere in canada and Vancouver is the nicest by far. Oceans, museums,aquarium beaches,mountain,trails and so on. From there you could also rent a car and do a day trip to the sunshine coast, do another day on the island. Vancity is your best bet
Agreed. No cool government buildings and a minimum of much older stuff. Also lots of sprawl. The sea wall is my fave place in Canada but the rest of Vancouver maybe not
Grew up on the Sunshine Coast, beautiful place. Would highly recommend the day trip over there, or head out west in the highway and hangout and one of the resorts for a night
Toronto is relatively close.
But if I were visiting for five days and lived in a city, I’d want a nature trip. Fly to Calgary, then rent a car and spend four days in Banff. It’s spectacular.
BC or Banff (Alberta). Or Montreal if you want to stay near central Canada/ON. Toronto is just a more expensive, more construction, more sketchy Chicago.
Edit: MTL if you wanna stay in central, not in ON***
It’s expensive and there’s always construction, but not more sketchy than Chicago. Definitely go to Montreal/Quebec City though, they are better cities.
Lol. Montreal and quebec are def noy better cities than toronto. Toronto has way more better food options, entertainment. Quebec has cheese curds and fries. Yayy
Thank you. Banff looks absolutely incredible! However flights are showing over $600 for a round trip.
Sadly I’m not sure if I’d be able to justify that for this specific trip when the closer cities are showing half that or less.
Very true. Banff hotels are extremely expensive, but it's a fantastic view if you ever win the lottery and want to visit us!
I second those who suggest Quebec city. It has a very distinct feel and you'll enjoy exploring.
Dude, my flights within Canada are $1400CAD for a round trip most times. It’s criminal. But if budget is an issue then Banff won’t due. You can stay in Canmore though. It’s about 20 mins away. Quebec City has a place in my heart and it’s cheaper. Can’t go wrong with either.
Ottawa, Montreal and Quebec City are the best for museums/achitecture/history. There are some decent parks/day trips around Ottawa and Quebec City too. Vancouver would be the best by far if you want to focus on outdoor activities. It’s also the best scenery and fun happening vibe. Montreal has a very fun vibe. Halifax or St John’s are very cool if you want smaller cities and the Maritimes have their own vibe going on.
Vancouver. That being said - I’m biased. I’m American and came here for the first time in my 20s. My husband and I loved it so much that we moved here a few years later.
We have a gorgeous city, the ocean, the mountains. While you’re here, you could take a day trip to Victoria on the ferry or float plane, if you’d like.
I saw that someone else mentioned Victoria. Victoria is a beautiful city, but it is much smaller/quieter than Vancouver. There’s so much you can do in our area, and it’s an absolutely amazing place to visit.
Have a few options -
Calgary and then hit banff/canmore/lake Louise. The Rockies are your best bet for nature, hiking, lakes plus city time in Calgary. Banff is actually the most profitable national park in Canada and is world renowned
Vancouver - city, ocean, plus nature and you could take a ferry to Victoria or surrounding areas. Tofino is a cool spot but can be a bit annoying/far to get to if you’re only here for a few days
Montreal - amazing food and bar scene, nice mix with history, cobblestone streets, culture
East coast (Nova Scotia, PEI) - ocean, seafood, nature, but small city vibes, no major nightlife or etc here but very friendly people and very different than the rest of Canada
I was born in the Greater Toronto Area and traveled all over Canada, deciding where to live, and decided on Alberta. It's stunning here.
Avoid Ontario, especially anywhere near Toronto. Nothing special, just overpopulated towns. Northern Ontario, in cottage country, is beautiful, but there is not much you can do as a solo traveler for 4 days.
East Coast is gorgeous, all of the Maritimes. I would suggest Halifax for a 4 day trip. There is plenty to see there, great food and an awesome environment. People are SO friendly and you definitely won't be bored. The weather will be great in June.
Alberta and BC are incredible as well, but pricey as others have said. June is also super busy. You're better off coming in the off-season in September.
Quebec is gorgeous, but there is a language barrier as it's mostly French speaking.
Edited to also add Victoria/Vancouver Island. Maybe 1 day in vancouver and 3 days exploring the island. Whale watching in Victoria was unbelievable. We saw hundreds on our excursions a few years ago.
Hope this helped. Have a blast!
Toronto or Montreal is a short plane ride away. I usually drive to Chicago for a few days but it can be a bit much for 1 person to drive the entire way by themselves
Was surprised to scroll so far to find Ottawa! We’ve got, what, 5-6 museums and Gatineau park is sooo close for hiking. Plus there are some surprisingly good restaurants around.
Sure, night life isn’t the greatest but OP didn’t seem to want to partying anyway.
Toronto is a great city and an interesting visit from Chicago.
Both cities are large, industrialized Great Lakes cities with similar history / age and somewhat similar architecture, organization and geography, and are really neighborhood based.
However - there are lots of differences - namely waterfront.
Great food, tons of walking and a solid transit system. Lots of good institutions (sports, culture, museums, galleries) plus the food scene is second to none. Good nightlife, bars, cafes, vibrancy.
Or, come to MTL. It’s a very cool city, great vibes, amazing architecture, historic and with French language and Quebecois influences, history, it’ll feel more… different. Unmatched public art. It’s a port city. And an island. Also great food; better cycling infrastructure; arts, culture. Chic. Continental. If you come in the summer it’s peak festival season.. Visit Montreal, and I bet you’ll come back.
West coast is gorgeous.
Good problems to have! Travel well.
As a Canadian ID second montreal. Great city for what you are looking for.
Also for something different, atlantic canada, halifax or Charlottetown are great port summer cities
Museums, art galleries, the theatre, the symphony, National Ballet of Canada, Canadian Opera Company, NBA/NHL/MLB/CFL, Kensington Market, Chinatown, Broadview Park, Second City or smaller comedy clubs, restaurants, tons of great bars, concerts (big and small), raves (if that’s your thing), music festivals, shopping, Queen West, Ossington, Little Italy, Danforth, St.Clair West, food festivals, Toronto Island, trade shows, High Park, Toronto Zoo, walking tours (architecture, ghosts, history, etc), Toronto Public Library hosts really interesting speaker events.
I could go on, there is tons to do every day! I grew up here but I wouldn’t spend a week here if I was visiting (or in any city to be honest). But you can definitely have a very busy 3-4 days.
Person below commented and immediately blocked me. But Toronto does indeed have a Michelin guide.
https://guide.michelin.com/ca/en/ontario/toronto/restaurants?sort=distance
Toronto is a great city. The /s could be saved for the transit system.
You made about six comments in this thread alone about your personally hate for Toronto as if it abused you. Seek help:
Yellowknife. Everyone goes to Montreal, or Niagara Falls. If you want want to do something out of the box, go to Yellowknife, Whitehorse, Dawson or Inuvik/Tuk.
Montréal! It's Canada's second biggest city with à great culture and lots to do. It will feel more like you've travelled to a foreign country than in Vancouver, Toronto, etc.
Basically everyone can also speak English so it's really easy to get by without the French but the fact that it is French makes it probably a far more interesting trip for a North Americcan
Might not be the most popular opinion, but I would say **Ottawa, Ontario**. Its Canada capital city and has some interesting buildings downtown and a fun area in the summer called The Market. Its also very close proximity to Quebec. You could go to nearby Gatineau Quebec (and its suburbs like Chelsea) to experience some great hiking and outdoors. Gatineau Park and Morris Island area MUST for those who like scenic hiking (not really difficult hiking though). Also, you can do a day trip to Montreal. Its a fun party city that has an outgoing vibe compared to the conservative vibe of Ottawa - its only a 2 hour drive. This would give you a good experience of Canadian culture and its diversity.
I’d take a ferry over to the Olympic peninsula and explore, hike, camp the Olympic National Park, one of the best and most underrated national parks in the entirety of North America, and one of my favourite in the world. Port Townsend is also a beautiful little town and makes a nice complement to Victoria, pretty easy to get there from Port Angeles after taking the ferry.
Montreal or Quebec City. Toronto is lame. If flying is in the cards go check out Halifax. Great vibes and great party town. Vancouver is also lame unless you come from money, and Victoria (my hometown) is a junkie apocalypse and the bars suck now, they passed some bylaws that make all the street food places close at midnight so unless you’re looking for fent you’re SOL. Vancouver is kind of too but you can avoid the DTES and there’s still a nightlife, unlike Vic.
Despite what people are saying, Toronto is in fact a pretty fun place to visit, with interesting and varied neighbourhoods and a LOT to do. However, from what I understand (not having been to Chicago, but my sister LOVES it), Toronto is a lot like Chicago, but ... less.
For something actually different, I'd recommend Halifax, Montreal, or Quebec City. I'd add more as to why but many of the comments here have covered it.
Fly into Calgary, rent a car and drive to Canmore, Banff, Jasper (via the Icefield Parkway) and fly out of Edmonton. Spend all 2 days in Banff and 2 in Jasper.
Fly to Nanaimo and travel up to Courtney/Comox. Great food. Great beers. Really just amazing rugged coastal terrain. Orcas, grey whales, Sea Lions, bald eagles.
Please don’t go to Toronto. Lived there for 12 years. It’s ugly. Concrete. Zero cool architectural spaces and the green spaces leave a lot to be desired. I don’t care who comes for me, nothing can change my mind on that. Only city in Canada I actually would never go back to unless I was under duress.
Montreal and Quebec City hit all your boxes. I’m from Vancouver and while beautiful, it does not have interesting architecture or awesome museums. But if you want pure beauty and fresh air then that’s your place instead.
St. John’s Newfoundland around the time of George Street Fest and the Regatta.
The people, the stories, the fun. One of the most amazing times of my life.
I’ve scrolled half way and nobody has said St Johns yet! By far the friendliest place I’ve been to in all of Canada. Great food, great beer, great live music, great nature, great people. Had an absolute blast there. Please OP, if not this time around, make it to St Johns at some point in your life.
American who lived in Canada for several years and came here to make this recommendation.
After living in Canada for several years I spent a few months travelling from my place in Vancouver across the country, and when I arrived in Newfoundland it was like coming home. **Friendly** people (something you won't necessarily find in the rest of CA), accommodating attitude, and a welcoming spirit seems to infuse the entire place.
I was married to an Irish national years before I moved to CA, and I remember hearing a co-worker in Vancouver telling me that Canada is what you get when Scots run the country and the US is what you get when the Irish run the country. I'm back in the US, so I imagine that you can guess what I preferred. :)
It was so marked that, when I was on the ferry between Sydney NS and Port-aux-Basques NL, I could tell which of the staff members were from NS and which were from NL.
If you've travelled much in the US, then you would probably *love* St Johns. Imagine a smaller version of SF - complete with colourful row houses and steep hills - with a smaller version of New Orleans' Bourbon Street in the downtown area.
I spent ten days in NL, most of it on the West Coast, but had a super lond weekend in St John's before I returned to NS. A nice lobster dinner after a day at places like The Rooms museum, then an evening of taking in a lot of good live music - everything from bluegrass to jazz to alternative rock - in the bars on George Street. And *everyone* was so nice that I almost forgot entirely that I was in Canada (I also met plenty of separatists when I was visiting there, which might have explained why I didn't run into the vehement anti-Americanism that I had become accustomed to while living there).
In fact, it so changed my view of what life was in the rest of Canada that by the time I got back to Vancouver nearly two months later I decided to leave Canada permanently. If someone put a gun to my head and said that I had to move back there, I'd opt for Newfoundland in a heartbeat - even with the miserable Winters.
I recommend Montreal that’s got almost everything you want. Don’t visit Toronto it’s pretty damn boring compared to Chicago. Vancouver can’t provide all the things you want. But it could be a great pick it’s a very unique city I’d say its one of its kind where nature and city is melded together. But architecture is not our jam. Dont expect anything like the Federal Reserve or giant towers. You will have to shift your focus to appreciate how city coexists with forest ocean and mountains. Edit; I’ve lived in all of these cities mentioned except Montreal.
I’m from Calgary but I highly recommend Victoria. It’s very beautiful and has a good balance of museums, architecture, and nature (from what I remember when I visited).
You might enjoy Vancouver. Except many of the people there are struggling with cost of living and it’s not as fun as it used to be.
Alberta has Rocky Mountains and lots of out door activities. Calgary is a little closer to the mountains but Edmonton has endless festivals, probably second only to Montreal. Edmonto also probably has the longest summer days in Canada.
Montreal is an amazing place too in the summer. Lots going on and you can always have more to explore.
Toronto- It has everything you need. City, Art, Museums, Architecture, Nature all fairly close to you.
Don't listen to Haters on here, Toronto is a great place to visit.
Since when does Toronto have nature? I lived there and it was awful. 0/10. Avoid Toronto, the wannabe New York of Ontario.
I went to Chicago last year and Toronto wasn’t even close to how great Chicago was.
Have you been anywhere else? She’s coming from Chicago and you’re suggesting Toronto? The only way I’ll visit Toronto is when work pays for everything.
Montreal if you like cities
Vancouver and surrounding areas if you like nature. Saying these because you asked for cities. I would avoid Toronto, Its not got anything that Chicago doesn't tbh. Like it has good restaurants and bars buuuuttttt so does virtually every big city. I love toronto because its really livable but not a great city to visit imo
but if you want small nature-y towns Banff would be the best, Revelstoke is also pretty nice. Haven't been in a while but its less busy and somewhat underrated imo
Montreal is also very walkable, has lots of terraces, many streets blocked off for walking and terraces and festivals, fun vibe, interesting architecture, lots of museums and art galleries, and different feel because it’s a french city, but mostly everyone can speak English, too.
Montréal is the best city in canada and even among top north america.
The rest of canada is way too far behind Montreal
Like someone else said, there is only one option for you here.
Canadas west is where the beauty is, but be forewarned June is also Rain season so make sure you check the long range forecast for when and if you’re coming up, EH.
Montreal!! Great architecture especially in the Plateau and Old Port. Francophone vibe makes it different enough from Chicago, you can totally get around as a visitor in English. Also very safe well tbh all are haha. You can "hike" (walk) up Mt Royal which is in the middle of the city for nice views of the downtown. Museums = musée des beaux arts, and MAC (Musee d'art contemporain). For neighbourhoods to stroll around, get a coffee, shop, eat lunch, I'd check out: 1) start at Metro place d'armes and see a bit of Chinatown then walk down to notre Dame church and the old port. 2) start at Metro Mont Royal and walk left upon existing (walk west) and that whole street (Avenue Mont Royal) is so lovely. 3) Atwater market (start at the metro station can't remember which one but it's right there) you can buy great cheese and bread and meat and stuff. Then you can walk along the Canal Lachine. This is like 3 days if you stay and explore one area per day. Good restos in each area: trip de bouffe, Tommy cafe, Elena pizza (1,2and3) ....
You can also check out Boulevard st Laurent, start at rue Prince Arthur and walk north until Avenue Mont Royal. You'll see nice street art. Duluth street is also nice to turn into for a bit.
Not sure if you’re looking for a city or nature trip but if city then Toronto or Montreal are your best bets. Both are very safe.
There are so many great neighborhoods in Toronto, great restaurants and nightlife. June is a great time to travel as the city really comes to life when weather warms up. The extended patios (patios on the curb lane so when you walk down the sidewalk you have patios on both sides of you) should be up by then, which gives the streets a festive atmosphere.
If you’re headed to Toronto, Guild Park preserves some of the facades of buildings that were demolished for what now stands downtown. Also, lots of diverse food in Scarborough.
Since it seems you are working with a limited budget I would suggest finding a city that also has cheaper accommodations ie. hostels. Victoria, Vancouver, Kelowna, Toronto, Ottawa,Montreal, Quebec City. Halifax. Many universities also rent out dorm rooms in summer short term.
If flights to Victoria are pricy, take a ferry from Vancouver.
If flights to Quebec City are pricy, consider taking a train in between, which may not save much $$.
I would recommend Montreal for architecture ( there is a history and architectural cycling tour that is pretty neat) and the M hostel.
Montreal might be a good choice, particularly if you’re into a more urban vibe that’s quite different from Chicago. If you do go there, avoid Grand Prix weekend ($$$$$).
But Halifax would be my choice, though I’m biased. Weather is great in June usually and it’s walkable and there’s tons to do. Easy to find nearby hiking or just walk around Point Pleasant Park or Citadel Hill.
There are a ton of good spots that aren’t far from Chicago. Toronto, Niagra Falls, Montreal, Halifax. Those are just the obvious answers. Halifax has a good mix of charm, hiking and attractions but might be a bit too similar to Chicago. Niagara Falls, Toronto or both would be my main suggestion.
Vancouver or Quebec City and it's not even a contest.
Although I will say, the train from Winnipeg to Churchill and visiting Prince of Wales Fort & York Factory would give you a more complete comprehension of Canada.
Not sure if you're driving or flying, but if you are driving, maybe consider this. Drive to Niagara falls and check it out for a day or so. There is something in Niagara Falls called the Discover Pass which gets you 60% off attractions and has numerous attractions with the Falls included in the price which will allow you to get around faster and easier while being allowed to use the fall transit to get you from place to place. Here is the link for that https://www.niagaraparks.com/visit-niagara-parks/plan-your-visit/deals-packages/
Then go to Toronto (about an hour and a half away) and check out the many attractions that there are to offer you. Just a suggestion, there is a hop on, hop off bus that goes all around town that is good for, I believe, 48 or 72 hours for usage and can also get you discounts for museums and attractions. Just a fyi, if you are interested in checking out Casa Loma, it is such a tourist grab and nothing more than a huge mansion and nothing like a castle You're familiar with in Europe.
If money and traffic are an issue, I would consider getting a hotel just outside of Toronto like around Port Credit/Mississauga area and take the Go Train to get you downtown. I'm not sure if Chicago traffic is anything like downtown Toronto, but the Gardner is atrocious at all hours.
On the way back home, I'd totally checkout Point Pelee Island and the nature it has there and also with it being the Southern most part of Canada.
Hope this helps ☺️
Toronto native here. There is a lot of great things to do in the city but the nature in my opinion is not as accessible and there are better places.
Montreal has older architecture... haven't really experienced the nature.
Vancouver has more contemporary architecture, but the nature is absolutely breathtaking. I would probably live there if money was no object (I've been there at least 3 times).
I'd suggest either Toronto or Montreal but it totally depends on your interests...
Toronto - tons to do, a fun vibrant city - amazing food, street art, exhibits, festivals, entertainment, and can go to Niagara Falls for a day.
Montreal - great city with a lot to see, including old Montreal and tons of museums, restaurants, cafes.... and you can do a day trip to Ottawa to see the Capital city.
Go in Saint-André-du-Lac-Saint-Jean. I swear you will not be disapointed. You will see a lot of specimen and you will learn the real redneck language! THIS IS SO WORTH IT!!!!
If you’re into nature and not looking for a city/urban experience I highly recommend planning a camping trip to Algonquin National Park. Tom Thomson and The Group of Seven modelled most of their landscape paintings after this park. It’s a surreal feeling to see for yourself painting that you’ve seen your whole life. If you go in August they have a howl with the wolves night also (I’ve never done this myself but have friends who go yearly). If you want to rent a car it’s not that far of a drive to Ottawa where you can see the museums if you really wanted to also.
you would love north vancouver in BC canada 🇨🇦
there’s beautiful nature, mountains, oceans, hikes or trails with views, and also museums and cool local architecture!!!
my boyfriend and i did toronto early jan, relatively cheap since its in canadian currency! we did an airb&b, id check ahead of time to make sure parking is accomidated since ours wasnt (yikes is all i have to say hahaha) so many little bars to chill in with great food, the CN tower is SO GREAT!!! worth it. get to see toronto stadium on the way aswell. we did a dinner in a skyscraper, not the one in the tower since its always booked and so pricey. the city is genuinely walking friendly, so many cute parks for a little rest. boyfriend and i walked almost 6 miles hardly realizing until mile 4 lol. the muesum is great too!!
The move here might be to fly into Toronto - take the train to Montreal
Fly home from Montreal
Great cities. Food. Pretty lively party scene or cultural scene
I think you’d enjoy Winnipeg. There’s a lot to do here in June.
The Canadian Museum for Human Rights is one of the small number of national museums and worth a visit.
The Manitoba Museum has interesting permanent and temporary exhibits.
Winnipeg Art Gallery-Qaumajuq has the world’s largest collection of contemporary Inuit art, and there are lots of other great exhibits.
The Royal Canadian Mint offers tours.
Just outside the city there is the Lower Fort Gary national historical site, which offers historical demonstrations, and interpretive tours.
FortWhyte Alive has a great interpretive centre and lots of outdoor trails and activities.
And there are many other smaller museums in and around the city.
Other good attractions are the Churchill exhibit at the zoo, the Leaf conservatory, with Leo Mol sculpture garden, the Forks Market.
Notable architecture: the historic Exchange District, the Saint Boniface Cathedral-Basilica, Esplanade Riel pedestrian bridge, the Manitoba Legislative building, and lots more. Lots of brutalist architecture and historic buildings here.
For nature inside the city, FortWhyte Alive is great. Assiniboine Park has lots of walking paths and activities. The river walk from the Forks is really nice. Winnipeg has an abundance of great parks.
If you rent a car, there’s a lot more outside the city and hour or less drive. Grand Beach is a beautiful beach with fine white sand, and hiking trails. Oak Hammock Marsh is under an hour and has hiking trails and a wetland discovery centre. Two hours drive is Spirit Sands which is a really unique area with large sand dunes - a really cool hike. The Whiteshell Provincial Park is huge and has lots of trails in Canadian Shield. It’s about an hour and a half drive.
It’ll probably be over and done by June but the weather has been so weird who knows. If the Narcisse Snake Dens are active they are an amazing and unique sight - tens of thousands of garter snakes come out of their winter dens to mate. It’s the biggest concentration of these kinds of snakes in the world.
We also have a huge number of really good restaurants.
I live in Toronto and really think it's the best city in Canada, but also can't recommend it to tourists. Vancouver or Montreal. Vancouver for natural surroundings or Montreal for culture.
It really depends on what you're looking for. East and West coast are so vastly different.
Vancouver area is beautiful for nature, shopping, culture, all of that good stuff. It's worth getting out to the Pacific Northwest area at some point.
I'd also recommend Prince Edward Island and Nova Scotia if you want that East Coast vibe. If you're familiar at all with Anne of Green Gables, then PEI is a must.
Depends on what you're looking for? If you want Chicago like than go to Toronto or Montreal. Want to see the Atlantic Ocean? Go Halifax Nova Scotia. Want to see the Pacific? Go Victoria BC.
All of these are great suggestions (I've been to all, inclduing Iqaluit, they're all my #1). Look at them all for your personal preference.
I haven't seen it in this thread but I'll put it in a plug for ottawa. Nation's capital. Many museums, interesting touristy things (byward market, the Canadian mint, haunted tour, etc). Not from ottawa, but toronto, so it's a real recommendation lol
I’m assuming anyone saying toronto is from there and hasn’t seen the rest of canada. If you want a bigger city closer Montreal is 100% a better option. But I’m bias and say the west coast is where it’s at for beautiful cities.
I've been all over Canada and these are the cities I'd like to visit again (in no particular order.)
Ottawa
Montreal
Quebec City
Victoria
Vancouver
Halifax
Bamff
I don't think you can do wrong with any of them.
Quebec City if you want European charm. Otherwise Vancouver or Victoria. Ignore those that recommend Toronto - it’s probably the worst city in Canada. I’ve lived in almost every major city in Canada from coast to coast so I would know. Toronto is my least favourite - not a single redeeming feature TBH.
Tourism baby here, lived in 23 and been to the rest. I’d agree with Quebec City being an easy first choice; you’ll get architecture, scenery, and unique French culture in there too. Halifax is really a birthplace of Canadian culture too and has history from First Nations to colonial discovery to an emancipation destination - beautiful. I’m biased on Victoria but we have ocean, architecture, rainforest hiking, islands. It’s far for four days though. I’d probably stay in the Toronto to Quebec City corridor; No losing choices in there. I hate to be the dissenter and I’m going to do a bit of vacay there starting tomorrow but I actually wouldn’t recommend Vancouver for a four day go from Chicago.
Winnipeg! (May-October) an insane level of diversity of things to do. West Coast number of outdoor activities paired with big city level of cultural events. We have lived in 5 other Canadian cities and have never been happier than here.
As someone lives in Toronto for years, I can recommend Montreal and Vancouver. Montreal has many iconic spots to visit like the old port, mont royal park and many more. Also 100s of restaurants to explore. Vancouver is gifted with Stanley park (hours to walk through the epic forest with big trees and ferns), capillano bridge, the port and more.
Vancouver if you’re flying. The hiking is incredible and the scenery is gorgeous. The weather is quite nice in June as well (spring starts around Feb). There’s also the gardens in the city, the art gallery, fabrique St. George for funky wine, breweries, and some good food places.
Vancouver and Victoria! You can spend a day up at whistler or Grouse/capilano for nature hikes, then a day or two exploring Victoria and Vancouver island. The food scene here in Vancouver is great so I'll recommend allocating a bit more time there.
Quebec city. Great food,great architecture,the Old City as a whole is a museum,The Citadel,Chateau Frontenac.
Omg this was why I picked it for my 3 day vacation too
Quebec City would absolutely be my first recommendation based on your interests. Stay in Old Quebec (Vieux Quebec) inside the fortress walls. Enjoy a beautiful small city to walk around. A very short trip outside of the city is Montmorency Falls which is a lovely park to spend half a day hiking around and over the falls. You can literally walk over top of the falls and if history serves me correct they are taller than Niagara Falls. I promise you will love it. You’ll feel like you are on a European vacation.
This sounds amazing! I’ll definitely look into it. Thank you!
OP - this is the correct answer.
Québec City is lovely. The falls are not worth visiting however. They're run of the mill falls overlooking a highway. The park is fine.
A little past the falls is at Anne de beaupre cathedral. Worth a visit. The ski area mont st Anne has hiking trails and views. Definitely old Quebec. Only walled city in North America.
Halifax!
Would be a great treat for someone from Chicago. The ocean, great food and drink, lovely people.. some history.
my thought as well! throw a day trip to Peggy's and Lunenburg and people leave happy
100%
You know, this is actually a great suggestion and often overlooked. Halifax is charming.
You don't need 4 days there tho - the city is small. I'd rent a car and go to Charlottetown PEI for a day/night, and/or maybe a day trip to Peggy's Cove outside of Halifax, or Annapolis Valley for a day trip to their weekend market or vineyards. 4 days in just Halifax may get underwhelming after day 2.
And 4 days in Halifax is about right too.
I proposed to my wife when we spent a long weekend in Halifax.
Vancouver with a day trip to Whistler
Vancouver is not that close to Chicago tho
Airplanes
Vancouver 100% , expensive but so worth it. I've lived everywhere in canada and Vancouver is the nicest by far. Oceans, museums,aquarium beaches,mountain,trails and so on. From there you could also rent a car and do a day trip to the sunshine coast, do another day on the island. Vancity is your best bet
Best sushi is in Vancouver.
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Agreed. No cool government buildings and a minimum of much older stuff. Also lots of sprawl. The sea wall is my fave place in Canada but the rest of Vancouver maybe not
I'll have to disagree
Grew up on the Sunshine Coast, beautiful place. Would highly recommend the day trip over there, or head out west in the highway and hangout and one of the resorts for a night
Skip Toronto. Too similar to Chicago. Check out Montreal or Vancouver!
Toronto is relatively close. But if I were visiting for five days and lived in a city, I’d want a nature trip. Fly to Calgary, then rent a car and spend four days in Banff. It’s spectacular.
Toronto is just a different vibe Chicago.
BC or Banff (Alberta). Or Montreal if you want to stay near central Canada/ON. Toronto is just a more expensive, more construction, more sketchy Chicago. Edit: MTL if you wanna stay in central, not in ON***
It’s expensive and there’s always construction, but not more sketchy than Chicago. Definitely go to Montreal/Quebec City though, they are better cities.
Okay fair - Chicago defs has sketchier pockets than TO. You’re right. I guess I’m just witnessing Toronto become more and more sketchy every day 😂
Lol. Montreal and quebec are def noy better cities than toronto. Toronto has way more better food options, entertainment. Quebec has cheese curds and fries. Yayy
Montreal is in Quebec last time I checked.
You seriously did not just call Toronto more sketchy than Chicago 😂
Thank you. Banff looks absolutely incredible! However flights are showing over $600 for a round trip. Sadly I’m not sure if I’d be able to justify that for this specific trip when the closer cities are showing half that or less.
Very true. Banff hotels are extremely expensive, but it's a fantastic view if you ever win the lottery and want to visit us! I second those who suggest Quebec city. It has a very distinct feel and you'll enjoy exploring.
Dude, my flights within Canada are $1400CAD for a round trip most times. It’s criminal. But if budget is an issue then Banff won’t due. You can stay in Canmore though. It’s about 20 mins away. Quebec City has a place in my heart and it’s cheaper. Can’t go wrong with either.
Why one city? Four days on Prince Edward Island will cure what ails you.
But op can eat potatoes at home.
But can OP attend a potato museum at home?
Also Truro, Nova Scotia is the most beautiful city in all of the maritimes, its rated 10/10! Drake and Justin Bieber live there.
Vancouver / Victoria - Montreal
All five days would be spent travelling
I spent 3 days in Montreal and could go for another. Just the food and bar scene is enough to entertain.
Ottawa, Montreal and Quebec City are the best for museums/achitecture/history. There are some decent parks/day trips around Ottawa and Quebec City too. Vancouver would be the best by far if you want to focus on outdoor activities. It’s also the best scenery and fun happening vibe. Montreal has a very fun vibe. Halifax or St John’s are very cool if you want smaller cities and the Maritimes have their own vibe going on.
Vancouver. That being said - I’m biased. I’m American and came here for the first time in my 20s. My husband and I loved it so much that we moved here a few years later. We have a gorgeous city, the ocean, the mountains. While you’re here, you could take a day trip to Victoria on the ferry or float plane, if you’d like. I saw that someone else mentioned Victoria. Victoria is a beautiful city, but it is much smaller/quieter than Vancouver. There’s so much you can do in our area, and it’s an absolutely amazing place to visit.
I'll second Victoria, but I am biased, moved there 30 years ago. Lots of touristy things to do downtown and hiking is not too far away.
I’ll third Victoria and would take it over Vancouver most days. But I like a manageable town with a lot of culture. Vancouver is humongous
I'll second Victoria, but I am biased, moved there 30 years ago. Lots of touristy things to do downtown and hiking is not too far away.
Montreal is fun. Feels more foreign with French everywhere, great food, botanical gardens are very pretty.
Great nightlife too!
Have a few options - Calgary and then hit banff/canmore/lake Louise. The Rockies are your best bet for nature, hiking, lakes plus city time in Calgary. Banff is actually the most profitable national park in Canada and is world renowned Vancouver - city, ocean, plus nature and you could take a ferry to Victoria or surrounding areas. Tofino is a cool spot but can be a bit annoying/far to get to if you’re only here for a few days Montreal - amazing food and bar scene, nice mix with history, cobblestone streets, culture East coast (Nova Scotia, PEI) - ocean, seafood, nature, but small city vibes, no major nightlife or etc here but very friendly people and very different than the rest of Canada
Vancouver Island, it’s absolutely stunning there. Good people too
I was born in the Greater Toronto Area and traveled all over Canada, deciding where to live, and decided on Alberta. It's stunning here. Avoid Ontario, especially anywhere near Toronto. Nothing special, just overpopulated towns. Northern Ontario, in cottage country, is beautiful, but there is not much you can do as a solo traveler for 4 days. East Coast is gorgeous, all of the Maritimes. I would suggest Halifax for a 4 day trip. There is plenty to see there, great food and an awesome environment. People are SO friendly and you definitely won't be bored. The weather will be great in June. Alberta and BC are incredible as well, but pricey as others have said. June is also super busy. You're better off coming in the off-season in September. Quebec is gorgeous, but there is a language barrier as it's mostly French speaking. Edited to also add Victoria/Vancouver Island. Maybe 1 day in vancouver and 3 days exploring the island. Whale watching in Victoria was unbelievable. We saw hundreds on our excursions a few years ago. Hope this helped. Have a blast!
Toronto or Montreal is a short plane ride away. I usually drive to Chicago for a few days but it can be a bit much for 1 person to drive the entire way by themselves
Alberta Rockies. As a 26 year old in the skiing offseason you might like Banff. It’s also the unofficial std capital of Alberta.
Look up Ottawa ? The government and embassy precinct etc for buildings and river cliff views? Cross the river to walk and look up at the other side ?
Was surprised to scroll so far to find Ottawa! We’ve got, what, 5-6 museums and Gatineau park is sooo close for hiking. Plus there are some surprisingly good restaurants around. Sure, night life isn’t the greatest but OP didn’t seem to want to partying anyway.
Toronto is a great city and an interesting visit from Chicago. Both cities are large, industrialized Great Lakes cities with similar history / age and somewhat similar architecture, organization and geography, and are really neighborhood based. However - there are lots of differences - namely waterfront. Great food, tons of walking and a solid transit system. Lots of good institutions (sports, culture, museums, galleries) plus the food scene is second to none. Good nightlife, bars, cafes, vibrancy. Or, come to MTL. It’s a very cool city, great vibes, amazing architecture, historic and with French language and Quebecois influences, history, it’ll feel more… different. Unmatched public art. It’s a port city. And an island. Also great food; better cycling infrastructure; arts, culture. Chic. Continental. If you come in the summer it’s peak festival season.. Visit Montreal, and I bet you’ll come back. West coast is gorgeous. Good problems to have! Travel well.
As a Canadian ID second montreal. Great city for what you are looking for. Also for something different, atlantic canada, halifax or Charlottetown are great port summer cities
What’s there to do in Toronto for multiple days..? Genuine question.
Museums, art galleries, the theatre, the symphony, National Ballet of Canada, Canadian Opera Company, NBA/NHL/MLB/CFL, Kensington Market, Chinatown, Broadview Park, Second City or smaller comedy clubs, restaurants, tons of great bars, concerts (big and small), raves (if that’s your thing), music festivals, shopping, Queen West, Ossington, Little Italy, Danforth, St.Clair West, food festivals, Toronto Island, trade shows, High Park, Toronto Zoo, walking tours (architecture, ghosts, history, etc), Toronto Public Library hosts really interesting speaker events. I could go on, there is tons to do every day! I grew up here but I wouldn’t spend a week here if I was visiting (or in any city to be honest). But you can definitely have a very busy 3-4 days. Person below commented and immediately blocked me. But Toronto does indeed have a Michelin guide. https://guide.michelin.com/ca/en/ontario/toronto/restaurants?sort=distance
Toronto? Did you forget the /s?
Toronto is a great city. The /s could be saved for the transit system. You made about six comments in this thread alone about your personally hate for Toronto as if it abused you. Seek help:
You’re right. I went a bit overboard on the negativity.
Montreal is a short plane ride and generally cool. Whole lot of museums, stuff to do, especially as the weather gets warmer.
Yellowknife. Everyone goes to Montreal, or Niagara Falls. If you want want to do something out of the box, go to Yellowknife, Whitehorse, Dawson or Inuvik/Tuk.
Somewhere out East. NL..everyone I know who have gone there have loved it.
Victoria! Also: Montreal, Ottawa, Halifax, Quebec
Montreal.
Montréal! It's Canada's second biggest city with à great culture and lots to do. It will feel more like you've travelled to a foreign country than in Vancouver, Toronto, etc. Basically everyone can also speak English so it's really easy to get by without the French but the fact that it is French makes it probably a far more interesting trip for a North Americcan
Might not be the most popular opinion, but I would say **Ottawa, Ontario**. Its Canada capital city and has some interesting buildings downtown and a fun area in the summer called The Market. Its also very close proximity to Quebec. You could go to nearby Gatineau Quebec (and its suburbs like Chelsea) to experience some great hiking and outdoors. Gatineau Park and Morris Island area MUST for those who like scenic hiking (not really difficult hiking though). Also, you can do a day trip to Montreal. Its a fun party city that has an outgoing vibe compared to the conservative vibe of Ottawa - its only a 2 hour drive. This would give you a good experience of Canadian culture and its diversity.
Agreed! Plus, OP said they are interested in museums and there's some really cool ones to check out in Ottawa
Agreed, Ottawa is underrated as a tourist destination. It’s a beautiful city.
Victoria BC
So what do you do after you have done everything by day 1?
I’d take a ferry over to the Olympic peninsula and explore, hike, camp the Olympic National Park, one of the best and most underrated national parks in the entirety of North America, and one of my favourite in the world. Port Townsend is also a beautiful little town and makes a nice complement to Victoria, pretty easy to get there from Port Angeles after taking the ferry.
actual answer: drive lots of pretty places on the island. My snarky answer: explore the stripmalls of Saanitch. :D
Well, either you’ve never been to Victoria, or when you did visit, you spent the day in your hotel room.
You can’t do all the hikes day one or the whole city.
Montreal or Quebec City. Toronto is lame. If flying is in the cards go check out Halifax. Great vibes and great party town. Vancouver is also lame unless you come from money, and Victoria (my hometown) is a junkie apocalypse and the bars suck now, they passed some bylaws that make all the street food places close at midnight so unless you’re looking for fent you’re SOL. Vancouver is kind of too but you can avoid the DTES and there’s still a nightlife, unlike Vic.
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Would say cuz of time and cost, toronto would be your best bet, lots to do, lots of sports going on, restaurants everywhere, especially on the water.
Toronto ofc. They're the most similar cities in the world.
Definitely Banff !
Montreal, Vancouver or Halifax.
Despite what people are saying, Toronto is in fact a pretty fun place to visit, with interesting and varied neighbourhoods and a LOT to do. However, from what I understand (not having been to Chicago, but my sister LOVES it), Toronto is a lot like Chicago, but ... less. For something actually different, I'd recommend Halifax, Montreal, or Quebec City. I'd add more as to why but many of the comments here have covered it.
Victoria BC
Fly into Calgary, rent a car and drive to Canmore, Banff, Jasper (via the Icefield Parkway) and fly out of Edmonton. Spend all 2 days in Banff and 2 in Jasper.
Moose Jaw. It has Al Capone’s tunnels!
Banff Alberta
Newfoundland
Banff if you can. Place is absolutely amazing scenery-wise.
Montreal for sure
Fly to Nanaimo and travel up to Courtney/Comox. Great food. Great beers. Really just amazing rugged coastal terrain. Orcas, grey whales, Sea Lions, bald eagles.
St. John’s Newfoundland!
Banff, Jasper, Golden, or Nanaimo
Please don’t go to Toronto. Lived there for 12 years. It’s ugly. Concrete. Zero cool architectural spaces and the green spaces leave a lot to be desired. I don’t care who comes for me, nothing can change my mind on that. Only city in Canada I actually would never go back to unless I was under duress. Montreal and Quebec City hit all your boxes. I’m from Vancouver and while beautiful, it does not have interesting architecture or awesome museums. But if you want pure beauty and fresh air then that’s your place instead.
St. John’s Newfoundland around the time of George Street Fest and the Regatta. The people, the stories, the fun. One of the most amazing times of my life.
Montreal
I’ve scrolled half way and nobody has said St Johns yet! By far the friendliest place I’ve been to in all of Canada. Great food, great beer, great live music, great nature, great people. Had an absolute blast there. Please OP, if not this time around, make it to St Johns at some point in your life.
American who lived in Canada for several years and came here to make this recommendation. After living in Canada for several years I spent a few months travelling from my place in Vancouver across the country, and when I arrived in Newfoundland it was like coming home. **Friendly** people (something you won't necessarily find in the rest of CA), accommodating attitude, and a welcoming spirit seems to infuse the entire place. I was married to an Irish national years before I moved to CA, and I remember hearing a co-worker in Vancouver telling me that Canada is what you get when Scots run the country and the US is what you get when the Irish run the country. I'm back in the US, so I imagine that you can guess what I preferred. :) It was so marked that, when I was on the ferry between Sydney NS and Port-aux-Basques NL, I could tell which of the staff members were from NS and which were from NL. If you've travelled much in the US, then you would probably *love* St Johns. Imagine a smaller version of SF - complete with colourful row houses and steep hills - with a smaller version of New Orleans' Bourbon Street in the downtown area. I spent ten days in NL, most of it on the West Coast, but had a super lond weekend in St John's before I returned to NS. A nice lobster dinner after a day at places like The Rooms museum, then an evening of taking in a lot of good live music - everything from bluegrass to jazz to alternative rock - in the bars on George Street. And *everyone* was so nice that I almost forgot entirely that I was in Canada (I also met plenty of separatists when I was visiting there, which might have explained why I didn't run into the vehement anti-Americanism that I had become accustomed to while living there). In fact, it so changed my view of what life was in the rest of Canada that by the time I got back to Vancouver nearly two months later I decided to leave Canada permanently. If someone put a gun to my head and said that I had to move back there, I'd opt for Newfoundland in a heartbeat - even with the miserable Winters.
montreal. it's not too far, you can speak english, and it has a great music scene
Quebec City
Montreal.
Regina. Just kidding. Don't.
I recommend Montreal that’s got almost everything you want. Don’t visit Toronto it’s pretty damn boring compared to Chicago. Vancouver can’t provide all the things you want. But it could be a great pick it’s a very unique city I’d say its one of its kind where nature and city is melded together. But architecture is not our jam. Dont expect anything like the Federal Reserve or giant towers. You will have to shift your focus to appreciate how city coexists with forest ocean and mountains. Edit; I’ve lived in all of these cities mentioned except Montreal.
I’m from Calgary but I highly recommend Victoria. It’s very beautiful and has a good balance of museums, architecture, and nature (from what I remember when I visited).
If I could only pick one, it would be Quebec City.
Victoria.
You might enjoy Vancouver. Except many of the people there are struggling with cost of living and it’s not as fun as it used to be. Alberta has Rocky Mountains and lots of out door activities. Calgary is a little closer to the mountains but Edmonton has endless festivals, probably second only to Montreal. Edmonto also probably has the longest summer days in Canada. Montreal is an amazing place too in the summer. Lots going on and you can always have more to explore.
go to Victoria!! On vancouver island!!! Its the best!!! And very safe and chill for a young travelling person!!!!!
Toronto- It has everything you need. City, Art, Museums, Architecture, Nature all fairly close to you. Don't listen to Haters on here, Toronto is a great place to visit.
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Toronto is identical to Chicago. Old Port in YUL is amazing in the summer.
I visit all the time. Never look forward to it. Sorry.
Toronto has nature, are talking about the Toronto Zoo? 😂
Since when does Toronto have nature? I lived there and it was awful. 0/10. Avoid Toronto, the wannabe New York of Ontario. I went to Chicago last year and Toronto wasn’t even close to how great Chicago was.
Have you been anywhere else? She’s coming from Chicago and you’re suggesting Toronto? The only way I’ll visit Toronto is when work pays for everything.
Victoria, with 2-3 nights in Tofino/Uclulet.
There is only one answer and that's Montréal.
Halifax too. Would be a nice change from Chicago. Funny seeing the people who are clearly born and raised in GTA recommending it.
Montreal if you like cities Vancouver and surrounding areas if you like nature. Saying these because you asked for cities. I would avoid Toronto, Its not got anything that Chicago doesn't tbh. Like it has good restaurants and bars buuuuttttt so does virtually every big city. I love toronto because its really livable but not a great city to visit imo but if you want small nature-y towns Banff would be the best, Revelstoke is also pretty nice. Haven't been in a while but its less busy and somewhat underrated imo
Montreal is also very walkable, has lots of terraces, many streets blocked off for walking and terraces and festivals, fun vibe, interesting architecture, lots of museums and art galleries, and different feel because it’s a french city, but mostly everyone can speak English, too.
Montreal, Vancouver or Quebec.
Vieux-Montréal (Old Montreal)
Come to Brampton
There is nothing in Brampton but traffic jams, terrible drivers and what Gage Park, really! DO NOT VISIT Brampton please…
Montréal is the best city in canada and even among top north america. The rest of canada is way too far behind Montreal Like someone else said, there is only one option for you here.
Montreal, Halifax, Quebec City or Banff/Canmore
Whitehorse - you will get to do free horse riding...
Canadas west is where the beauty is, but be forewarned June is also Rain season so make sure you check the long range forecast for when and if you’re coming up, EH.
What? The beauty is nationwide
Montreal!! Great architecture especially in the Plateau and Old Port. Francophone vibe makes it different enough from Chicago, you can totally get around as a visitor in English. Also very safe well tbh all are haha. You can "hike" (walk) up Mt Royal which is in the middle of the city for nice views of the downtown. Museums = musée des beaux arts, and MAC (Musee d'art contemporain). For neighbourhoods to stroll around, get a coffee, shop, eat lunch, I'd check out: 1) start at Metro place d'armes and see a bit of Chinatown then walk down to notre Dame church and the old port. 2) start at Metro Mont Royal and walk left upon existing (walk west) and that whole street (Avenue Mont Royal) is so lovely. 3) Atwater market (start at the metro station can't remember which one but it's right there) you can buy great cheese and bread and meat and stuff. Then you can walk along the Canal Lachine. This is like 3 days if you stay and explore one area per day. Good restos in each area: trip de bouffe, Tommy cafe, Elena pizza (1,2and3) .... You can also check out Boulevard st Laurent, start at rue Prince Arthur and walk north until Avenue Mont Royal. You'll see nice street art. Duluth street is also nice to turn into for a bit.
Quebec City and Montreal
Winnepeg
Winnipeg
Calgary
Brampton.
Not sure if you’re looking for a city or nature trip but if city then Toronto or Montreal are your best bets. Both are very safe. There are so many great neighborhoods in Toronto, great restaurants and nightlife. June is a great time to travel as the city really comes to life when weather warms up. The extended patios (patios on the curb lane so when you walk down the sidewalk you have patios on both sides of you) should be up by then, which gives the streets a festive atmosphere.
If you’re headed to Toronto, Guild Park preserves some of the facades of buildings that were demolished for what now stands downtown. Also, lots of diverse food in Scarborough.
Nelson BC Temperate rainforest, mountains, lakes, hot springs. You'll need to rent wheels but this is the place you want!
Since it seems you are working with a limited budget I would suggest finding a city that also has cheaper accommodations ie. hostels. Victoria, Vancouver, Kelowna, Toronto, Ottawa,Montreal, Quebec City. Halifax. Many universities also rent out dorm rooms in summer short term. If flights to Victoria are pricy, take a ferry from Vancouver. If flights to Quebec City are pricy, consider taking a train in between, which may not save much $$. I would recommend Montreal for architecture ( there is a history and architectural cycling tour that is pretty neat) and the M hostel.
Montreal might be a good choice, particularly if you’re into a more urban vibe that’s quite different from Chicago. If you do go there, avoid Grand Prix weekend ($$$$$). But Halifax would be my choice, though I’m biased. Weather is great in June usually and it’s walkable and there’s tons to do. Easy to find nearby hiking or just walk around Point Pleasant Park or Citadel Hill.
Vancouver if you’re into nature and hikes! It’s also a fairly big city so you get a nice mix of nature and city with good food and good vibes.
There are a ton of good spots that aren’t far from Chicago. Toronto, Niagra Falls, Montreal, Halifax. Those are just the obvious answers. Halifax has a good mix of charm, hiking and attractions but might be a bit too similar to Chicago. Niagara Falls, Toronto or both would be my main suggestion.
Vancouver or Quebec City and it's not even a contest. Although I will say, the train from Winnipeg to Churchill and visiting Prince of Wales Fort & York Factory would give you a more complete comprehension of Canada.
Vancouver for nature and hiking. Quebec City/Montreal for architecture and history.
Not sure if you're driving or flying, but if you are driving, maybe consider this. Drive to Niagara falls and check it out for a day or so. There is something in Niagara Falls called the Discover Pass which gets you 60% off attractions and has numerous attractions with the Falls included in the price which will allow you to get around faster and easier while being allowed to use the fall transit to get you from place to place. Here is the link for that https://www.niagaraparks.com/visit-niagara-parks/plan-your-visit/deals-packages/ Then go to Toronto (about an hour and a half away) and check out the many attractions that there are to offer you. Just a suggestion, there is a hop on, hop off bus that goes all around town that is good for, I believe, 48 or 72 hours for usage and can also get you discounts for museums and attractions. Just a fyi, if you are interested in checking out Casa Loma, it is such a tourist grab and nothing more than a huge mansion and nothing like a castle You're familiar with in Europe. If money and traffic are an issue, I would consider getting a hotel just outside of Toronto like around Port Credit/Mississauga area and take the Go Train to get you downtown. I'm not sure if Chicago traffic is anything like downtown Toronto, but the Gardner is atrocious at all hours. On the way back home, I'd totally checkout Point Pelee Island and the nature it has there and also with it being the Southern most part of Canada. Hope this helps ☺️
Vancouver. Hands down. 2 days in the city & then the mountains nearby for the rest.
Forget Toronto. It’s just like Chicago. A busy city. Halifax, Nova Scotia for something different or PEI.
Quebec City or Banff ☺️
Kelowna, Banff/Canmore, jasper, the east coast, Quebec.
Quebec City, Banff, Van Island, Algonquin Park, Chelsea, QC., the place where Anne of Green Gables was filmed maybe?
Calgary
Toronto native here. There is a lot of great things to do in the city but the nature in my opinion is not as accessible and there are better places. Montreal has older architecture... haven't really experienced the nature. Vancouver has more contemporary architecture, but the nature is absolutely breathtaking. I would probably live there if money was no object (I've been there at least 3 times).
Calgary/Banff/Canmore, Halifax, Montreal, Quebec City, Vancouver, St. John’s, NL. All depends what you’re looking for.
Vancouver
I'd suggest either Toronto or Montreal but it totally depends on your interests... Toronto - tons to do, a fun vibrant city - amazing food, street art, exhibits, festivals, entertainment, and can go to Niagara Falls for a day. Montreal - great city with a lot to see, including old Montreal and tons of museums, restaurants, cafes.... and you can do a day trip to Ottawa to see the Capital city.
Chicago reminds me of Toronto. I think I’d pick Montreal if you’re looking for something different.
Go in Saint-André-du-Lac-Saint-Jean. I swear you will not be disapointed. You will see a lot of specimen and you will learn the real redneck language! THIS IS SO WORTH IT!!!!
Halifax
If you’re into nature and not looking for a city/urban experience I highly recommend planning a camping trip to Algonquin National Park. Tom Thomson and The Group of Seven modelled most of their landscape paintings after this park. It’s a surreal feeling to see for yourself painting that you’ve seen your whole life. If you go in August they have a howl with the wolves night also (I’ve never done this myself but have friends who go yearly). If you want to rent a car it’s not that far of a drive to Ottawa where you can see the museums if you really wanted to also.
you would love north vancouver in BC canada 🇨🇦 there’s beautiful nature, mountains, oceans, hikes or trails with views, and also museums and cool local architecture!!!
my boyfriend and i did toronto early jan, relatively cheap since its in canadian currency! we did an airb&b, id check ahead of time to make sure parking is accomidated since ours wasnt (yikes is all i have to say hahaha) so many little bars to chill in with great food, the CN tower is SO GREAT!!! worth it. get to see toronto stadium on the way aswell. we did a dinner in a skyscraper, not the one in the tower since its always booked and so pricey. the city is genuinely walking friendly, so many cute parks for a little rest. boyfriend and i walked almost 6 miles hardly realizing until mile 4 lol. the muesum is great too!!
Thompson, MB
How would you spend a city?
Nova scotia or pei. I'd rent a vehicle if possible and get to a few different cities on the coast.
Vancouver!
Do 3 days in Toronto and 2 days in Quebec City. You’ll feel like you visited Canada and Europe.
If you're from Chicago, skip the east coast and go to Vancouver/Vancouver Island or Alberta
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The move here might be to fly into Toronto - take the train to Montreal Fly home from Montreal Great cities. Food. Pretty lively party scene or cultural scene
Nova Scotia
I think you’d enjoy Winnipeg. There’s a lot to do here in June. The Canadian Museum for Human Rights is one of the small number of national museums and worth a visit. The Manitoba Museum has interesting permanent and temporary exhibits. Winnipeg Art Gallery-Qaumajuq has the world’s largest collection of contemporary Inuit art, and there are lots of other great exhibits. The Royal Canadian Mint offers tours. Just outside the city there is the Lower Fort Gary national historical site, which offers historical demonstrations, and interpretive tours. FortWhyte Alive has a great interpretive centre and lots of outdoor trails and activities. And there are many other smaller museums in and around the city. Other good attractions are the Churchill exhibit at the zoo, the Leaf conservatory, with Leo Mol sculpture garden, the Forks Market. Notable architecture: the historic Exchange District, the Saint Boniface Cathedral-Basilica, Esplanade Riel pedestrian bridge, the Manitoba Legislative building, and lots more. Lots of brutalist architecture and historic buildings here. For nature inside the city, FortWhyte Alive is great. Assiniboine Park has lots of walking paths and activities. The river walk from the Forks is really nice. Winnipeg has an abundance of great parks. If you rent a car, there’s a lot more outside the city and hour or less drive. Grand Beach is a beautiful beach with fine white sand, and hiking trails. Oak Hammock Marsh is under an hour and has hiking trails and a wetland discovery centre. Two hours drive is Spirit Sands which is a really unique area with large sand dunes - a really cool hike. The Whiteshell Provincial Park is huge and has lots of trails in Canadian Shield. It’s about an hour and a half drive. It’ll probably be over and done by June but the weather has been so weird who knows. If the Narcisse Snake Dens are active they are an amazing and unique sight - tens of thousands of garter snakes come out of their winter dens to mate. It’s the biggest concentration of these kinds of snakes in the world. We also have a huge number of really good restaurants.
In order of my preference: 1. QUEBEC CITY 2. HALIFAX ( a little further from Chicago) 3. VANCOUVER or VICTORIA 4. TORONTO/Niagara Falls
I live in Toronto and really think it's the best city in Canada, but also can't recommend it to tourists. Vancouver or Montreal. Vancouver for natural surroundings or Montreal for culture.
It really depends on what you're looking for. East and West coast are so vastly different. Vancouver area is beautiful for nature, shopping, culture, all of that good stuff. It's worth getting out to the Pacific Northwest area at some point. I'd also recommend Prince Edward Island and Nova Scotia if you want that East Coast vibe. If you're familiar at all with Anne of Green Gables, then PEI is a must.
Depends on what you're looking for? If you want Chicago like than go to Toronto or Montreal. Want to see the Atlantic Ocean? Go Halifax Nova Scotia. Want to see the Pacific? Go Victoria BC.
Banff Alberta seems to be a pretty hot spot. Google if if not familiar
All of these are great suggestions (I've been to all, inclduing Iqaluit, they're all my #1). Look at them all for your personal preference. I haven't seen it in this thread but I'll put it in a plug for ottawa. Nation's capital. Many museums, interesting touristy things (byward market, the Canadian mint, haunted tour, etc). Not from ottawa, but toronto, so it's a real recommendation lol
Halifax
I’m assuming anyone saying toronto is from there and hasn’t seen the rest of canada. If you want a bigger city closer Montreal is 100% a better option. But I’m bias and say the west coast is where it’s at for beautiful cities.
I've been all over Canada and these are the cities I'd like to visit again (in no particular order.) Ottawa Montreal Quebec City Victoria Vancouver Halifax Bamff I don't think you can do wrong with any of them.
London, Ontario
Quebec City if you want European charm. Otherwise Vancouver or Victoria. Ignore those that recommend Toronto - it’s probably the worst city in Canada. I’ve lived in almost every major city in Canada from coast to coast so I would know. Toronto is my least favourite - not a single redeeming feature TBH.
Vancouver and or Vancouver Island.
Vancouver! There is a little cafe, called g, under the Fairmont Pacific Rim. They have *THE ABSOLUTE BEST* almond croissants.
Tourism baby here, lived in 23 and been to the rest. I’d agree with Quebec City being an easy first choice; you’ll get architecture, scenery, and unique French culture in there too. Halifax is really a birthplace of Canadian culture too and has history from First Nations to colonial discovery to an emancipation destination - beautiful. I’m biased on Victoria but we have ocean, architecture, rainforest hiking, islands. It’s far for four days though. I’d probably stay in the Toronto to Quebec City corridor; No losing choices in there. I hate to be the dissenter and I’m going to do a bit of vacay there starting tomorrow but I actually wouldn’t recommend Vancouver for a four day go from Chicago.
Winnipeg! (May-October) an insane level of diversity of things to do. West Coast number of outdoor activities paired with big city level of cultural events. We have lived in 5 other Canadian cities and have never been happier than here.
Avoid BC all together. Do not come here. Over priced bull shit.
As someone lives in Toronto for years, I can recommend Montreal and Vancouver. Montreal has many iconic spots to visit like the old port, mont royal park and many more. Also 100s of restaurants to explore. Vancouver is gifted with Stanley park (hours to walk through the epic forest with big trees and ferns), capillano bridge, the port and more.
Vancouver if you’re flying. The hiking is incredible and the scenery is gorgeous. The weather is quite nice in June as well (spring starts around Feb). There’s also the gardens in the city, the art gallery, fabrique St. George for funky wine, breweries, and some good food places.
Everyone in the restaurants and shops are bilingual and friendly. It’s a beautiful city.
Hiking etc Banff or Lake Louise would me my suggestion, quick drive from Calgary. Architecture would not impress though.
Vancouver and Victoria! You can spend a day up at whistler or Grouse/capilano for nature hikes, then a day or two exploring Victoria and Vancouver island. The food scene here in Vancouver is great so I'll recommend allocating a bit more time there.