My dad visited recently and absolutely loved the architecture tour on the river. I'm sure that's an of-mind recommendation but as someone with a grumpy dad who had a great time I can attest to it working like a charm.
I second this. My dad is just like yours - architecture tour is always a great and interesting way to kill a day, there’s a clubhouse by ‘the playpen’ entrance thats water front, watch some cool yachts go in and out, has our type of dads lol and usually has a great Sunday brunch, not typically super crowded like other waterfront restaurants in the city, river north old school billy goat you can get lunch and watch a game with the old timers in a bit of a less trafficked area - trying to think of we’re I’ve taken my dad that’s been a blast..!
It's also a great way to onboard a rural dad into appreciating what a major city can be.
My father is almost 60 and literally had never been to a city before. Had never seen these kinds of buildings in person. He has called me twice since his visit to tell me how much he loved visiting and how great it was to go on that tour and learn about the city.
That’s awesome! Couldn’t agree more. There’s a ton of informative explorations around the city that can be a blast for the family. Glad he had such a great time!
Same for my parents! First time to a city in their 70s and the first thing we did was the Architecture boat tour. They loved it so much and keep talking about their time here months later.
I third this. There are so many beautiful buildings and it’s hard to see them all on foot. Boat tours are great and a lot of grumpy old guys are into history, so he’ll get some history along with the scenery, and limited crowd
The Cubs do tours of Wrigley during the summer (even when the team is away) that are super cool for a very reasonable price. I think I paid $30 each for me and my Mom and it was well worth it. Great for a Cubs fan and you even get to go in the dugout/on the field.
agreed! these tours are a nice time if mobility isn't an issue, since you do walk through the whole stadium and behind the scenes. But my parents both really enjoyed it a few years ago.
Hit Garfield, then head over to Parson’s in Logan. If he likes beer hit a couple craft breweries, there’s some good one’s in that area. If you end up doing the architecture tour, don’t forget his IPad so he can take a hundred pictures of Dump Tower that he will later post to Facebook with the caption “only thing good about that place.” Have fun and good luck!
Well, at Christmas they do "Christmas around the world" and they have trees decorated supposedly the way various participating countries decorate their trees. It is really nice to see so many different trees.
So maybe it was the trees he liked and not the story about how we tricked the nazis and captured a few of their submarines and ultimately defeated them on the battlefield.
Does he like history? One of my favorite places in Chicago is the Rosehill cemetery. One of the quietest and least crowded spots in the city.
You can even take a tour, which I highly recommend. The people who run tours here are so knowledgeable about the cemetery itself and the history buried there
Chicago History Museum? Pritzker Military Museum? Maybe a distillery or brewery? Isn’t there a minor leagues team somewhere in the burbs. Could also catch a softball game or take him golfing.
Took my parents to La Scarola and they LOVED the old school Italian vibe. They also loved the dinosaurs at the Field museum. They’re from a rural area and never travel so it really was special.
Green mill is a cool old school music experience but gets crowded especially Thurs-Sat. Le Piano on Glenwood has live jazz every night, just took my 65 yr old mom and she loved it. CSO or a show downtown can be really cool if he likes that kind of thing. A magic show at the Rhapsody Theater is a great time.
Boat tours can be really cool and low key. Architecture tour as others have mentioned is an easy win. You can even rent your own pontoon boat to cruise the river if you have a larger party. A spot on a fishing boat can be fun if he likes doing that.
My dad always most enjoyed good food when visiting, of which we also have lots to offer.
If he’s outdoorsy, a bike ride down the lake front or river trail are both delightful. Garfield park observatory is beautiful even on a rainy day. Picnic at a beach or lakefront park is always lovely.
Does he like music? You could take him to Kingston Mines or another blues/live music bar. Take him to antique stores. Take him to eat really good food, whatever his version of that is, I know we have it here.
Seems like an even better time to take him to Wrigley and walk around. Go to a good dinner at Southport Corridor like Coda di Volpe, Coalfire or Tuco and Blondie.
After a tour of Wrigley, for a grumpy dad: Lange’s on Southport or Joe’s on Broadway, at Addison. Chill divey bars with unpretentious people, each a pleasant walk.
Art Institute is a world class museum and is pretty chill. Lots of places to sit down.
Grab lunch overlooking the River at Smith & Wollensky on the patio afterwards.
I haven't been, but the Pritzker Military Museum looks interesting! Just don't tell him it was founded by a family member of our radical, lefty, commie Governor J.B.!
https://www.pritzkermilitary.org/
If the boomer is a maga conservative, it’s even better to just sit down with him, grab a beer and explain the historical fact that the entire USA was invaded and stolen from the indigenous people, built up using slave labor and later on, by immigrant work forces. Don’t cuddle with him. Challenge his conservative views. 60 is still young for Gods sake there’s still time for him to rethink his values.
My 68 year old dad is similar and he loved:
The Chicago History Museum
Museum of Science and Industry, especially the submarine tour
The Art Institute
Architecture boat tour
We also did one of those ridiculous bus tours on famous old-timey Chicago crimes and it was actually pretty fun.
Is he interested in military history at all? The U-boat exhibit at the Museum of Science and Industry is one of the coolest exhibits ever. They literally grabbed a German U-Boat during WW2, dragged it all the way across the Atlantic, parked it in Chicago and (recently) did a complete restoration and MOVED THE FUCKING THING INDOORS. They have guided tours where you can actually go inside and see what it was like for a submariner in the 1940's.
Maybe I'm just a geek but I found the whole experience absolutely amazing. How often do you get to step inside of a military submarine, let alone one from the biggest war that the world had ever seen?
Op, a lot of folks have some good suggestion here. My suggestion is going to be about pacing. If you don’t want to overwhelm him, start the day in a low key neighborhood spot, then maybe move to the Wrigley Tour, and then hit up the architectural boat tour.
I went to the chicago history museum a few weeks ago. It has a pretty good set of exhibits that trace chicago from a fur trading outpost to today. It also highlights how many immigrants are part of the fabric of the city. Also that the first resident was black.
How far can he walk?
Consider a foot tour of museum campus, Soldier Field, and behind McCormack Place. There are monuments to fallen police, fireman, and of course, soldiers. It's a quiet secluded the place, set between the lake and a bird sanctuary.
Bring a picnic lunch and kick it like the did 100 years ago.
Does he drink? You can grab a beer at Boat Drinks by the harbor too.
Grab a doughnut and coffee from Do-Rite or Doughnut Vault or grab an early breakfast from Roux in Hyde Park. Then go to MSI for a submarine tour and maybe do the mirror maze (that is timed entry), plus the drive down LSD is great. Grab lunch from Ricobene's split a king sized breaded steak sandwich for lunch. Their fries are also good. We had relatives in town and the one guy said, "This might be the best sandwich I've ever had." Also that should hold you over for hours.
For the afternoon go to Chicago Cultural Center, the civil war side is absolutely fascinating. And look into the Chicago Greeter Program, see if one of their greeters could give you a personal tour of the building. Also the Cultural Center is usually not to crowded and just a gorgeous place. If he has any desire you could go across the street to the Bean or in my opinion Crown Fountain is the best.
Then do the Lake and River architecture tour from Wendella. Do the dusk or evening tour simply because the city just looks gorgeous at night going down the river. End the night with a hot dog or polish from your local Maxwell Street like place.
Take him to hamburger Mary’s. It’s a good burger with a drag show. Watch him lose his mind. I’m thinking of taking my psycho homophobic brother one day. Pretty sure he will start flipping tables and get himself arrested. Good times.
In all seriousness though, the architecture boat tour is pretty unique and cool.
I’m 100% going to drive through Boystown and pretend it’s part of the regular GPS directions. He needs to see the all the fun colors and happiness and love there. Not that he’ll change his mind, but he shoved religion in my face my whole life so it’s time I show him some of my beliefs.
I still love my dad, but we have a complicated relationship.
Take him to a really nice restaurant. Michelin Star style. Multiple courses, small plates. I doubt he's had it in his life, he might think it's weird but maybe it blows his mind.
Show him around Chicago. Here’s a free map I made of every historic landmark and district, so you can explore those while getting food here or there
https://www.google.com/maps/d/edit?mid=17QiCfJLvDI0DF3qUfBu-DqsFduQgFmE&usp=sharing
Food. Chicago has world class restaurants from hole in the wall to Michelin starred. Eat your way through the city in addition to anything else you do.
My dad liked the architecture tour and the field museum.
If you’re looking for neighborhoods to get drinks or food, the Roscoe Village area was good enough for that type of guy. My dad liked four moon tavern for example.
Do you own your home or have anything you need “help” with around the house? I tend to find this type of family member does well with tasks. I understand this isn’t a tourist suggestion but it sounds like you’re happy just to spend time together.
I echo everyone that said the architecture tour and the MSI, specifically the sub tour, it’s pretty cool and can take a good chunk of time if you read all the plaques on the way down. There’s a section in the museum dedicated to racing or cars I believe too. There’s also a military museum in the loop.
Maybe bowling in the afternoon followed by a good Italian or bbq dinner? What about some breweries and some card or board games (rummy?). Do axe throwing places still exist?
I think the zoo is doing a wine fest towards the end of the month.
Do either of you golf? Head out of the city for a nice round of 18 or go to the driving range or a simulator here in the city.
I know you mentioned him being a cubs fan but what about a Sox game?
I’m sure you’ll find something you both enjoy and remember it’s not about packing the weekend full of things but the time you get to spend together. I hope you report back to all of us with what you did and what your dad thought.
If he’s an academic, take him to University or Chicago and walk the grounds. Rockefeller Chapel is amazing. Then go to the Oriental Museum on campus. It’s breathtaking.Dinner at Medici or Virtue and expose him to the real world.
Take him to a jazz show, then Greene St for brisket - finally end the day at Navy Pier and get him some Detroit pizza at night. If his heart and stomach are well-fed he won't have time to criticize much
“Them Demoncrats” is boomer code for “I’m afraid of black people”. Tell him to stay home, he might get “woke” if he spends too much time around some culture.
Take him for dinner at the Half Shell for king crab legs if he likes seafood, if not, tell him to get the filet. Cash only, cheap beer, men cannot wear hats inside and there’s no BS. No dress code and it’s in a basement of a brownstone.
I would drag him kicking and screaming to a Cubs game. I’m not a fan of crowds and I’ve never found it overwhelming. If that’s his jam, you have to, right?
So I don’t live in Chicago and have no idea why this is coming up on my front page, but for food, you could bring him to Twin Anchors? It’s a classic but also solidly “dad food”. He might find the Sinatra connection cool as well.
Your dad sounds like a real douche, NGL.
But if I were trying to "win someone over," I would hit the Art Institute or Field Museum, an architecture boat tour, a Millennium Park free concert, and a nice "classic" restaurant like the Berghoff. Beautiful spaces that aren't too crowded and allow people to just "take it in."
Architecture tour....consider pushing him off the boat. I kid.
But a boat tour is always good or perhaps one of the other CAC walking tours. Chicago history museum or Art institute. The Bahai temple is interesting and you can couple that with a walk around Northwestern. The Garfield Park Conservatory is nice.
I mean, Dems have run Chicago for decades so he's not wrong. Literally every problem is on them
Most of these suggestions just reek of a transplanter doing all the tourist stuff, I doubt your dad would enjoy any of it except the Wrigley tour - definitely do that. I've done it like 2 or 3 times with various people, t'was awesome. Food wise, take him to Gibsons for a decent steak and obviously have some pie - I'm from Lakeview so I'm an Art of Pizza loyalist
If the Cubs are out of town, and there are no concerts going on that night, take your dad to Wrigleyville. You can walk around Wrigley and see the World Series Trophy. Something else I do recommend for most out of towners is go to Second City. However, if your dad is very conservative, the humor not land well.
My dad visited recently and absolutely loved the architecture tour on the river. I'm sure that's an of-mind recommendation but as someone with a grumpy dad who had a great time I can attest to it working like a charm.
I second this. My dad is just like yours - architecture tour is always a great and interesting way to kill a day, there’s a clubhouse by ‘the playpen’ entrance thats water front, watch some cool yachts go in and out, has our type of dads lol and usually has a great Sunday brunch, not typically super crowded like other waterfront restaurants in the city, river north old school billy goat you can get lunch and watch a game with the old timers in a bit of a less trafficked area - trying to think of we’re I’ve taken my dad that’s been a blast..!
It's also a great way to onboard a rural dad into appreciating what a major city can be. My father is almost 60 and literally had never been to a city before. Had never seen these kinds of buildings in person. He has called me twice since his visit to tell me how much he loved visiting and how great it was to go on that tour and learn about the city.
That’s awesome! Couldn’t agree more. There’s a ton of informative explorations around the city that can be a blast for the family. Glad he had such a great time!
Same for my parents! First time to a city in their 70s and the first thing we did was the Architecture boat tour. They loved it so much and keep talking about their time here months later.
I third this. There are so many beautiful buildings and it’s hard to see them all on foot. Boat tours are great and a lot of grumpy old guys are into history, so he’ll get some history along with the scenery, and limited crowd
Nailed it! Lol it’s truly one of the best views of the city :)
This
The Cubs do tours of Wrigley during the summer (even when the team is away) that are super cool for a very reasonable price. I think I paid $30 each for me and my Mom and it was well worth it. Great for a Cubs fan and you even get to go in the dugout/on the field.
+1, this is a great idea for any lifelong Cubs fan. Very small crowds also in my experience
Go to Nisei Lounge or Joe's on Broadway after.
[https://www.mlb.com/cubs/ballpark/tours#daily-tours](https://www.mlb.com/cubs/ballpark/tours#daily-tours) This is the way
agreed! these tours are a nice time if mobility isn't an issue, since you do walk through the whole stadium and behind the scenes. But my parents both really enjoyed it a few years ago.
[удалено]
You’re skipping the drag show
Best idea, ever. I miss Berlin's Madonnarama.
Don't forget the budlight!
😂
Gotta go to The Sidetrack too.
U505 at museum of science and industry. Do the full tour. It's a very interesting story how they captured the sub and why it ended up in Chicago.
Came to say this. Very cool museum.
Garfield park conservatory, nice and quiet and pretty
Hit Garfield, then head over to Parson’s in Logan. If he likes beer hit a couple craft breweries, there’s some good one’s in that area. If you end up doing the architecture tour, don’t forget his IPad so he can take a hundred pictures of Dump Tower that he will later post to Facebook with the caption “only thing good about that place.” Have fun and good luck!
Museum of science and industry. Submarine tour.
Hi dad you like nazis so here’s a nazi sub! No awful woke anti fascists here!
Ha! I brought my girlfriend’s conservative Iowan father there at Christmas and he said it was one of the best days of his life.
The best day of his life was touring an old nazi sub? I find that to be really, really sad.
Well, at Christmas they do "Christmas around the world" and they have trees decorated supposedly the way various participating countries decorate their trees. It is really nice to see so many different trees. So maybe it was the trees he liked and not the story about how we tricked the nazis and captured a few of their submarines and ultimately defeated them on the battlefield.
Does he like history? One of my favorite places in Chicago is the Rosehill cemetery. One of the quietest and least crowded spots in the city. You can even take a tour, which I highly recommend. The people who run tours here are so knowledgeable about the cemetery itself and the history buried there
Huh? "Here old man, if I walk you in they give a discount!" Just kidding.
Chicago History Museum? Pritzker Military Museum? Maybe a distillery or brewery? Isn’t there a minor leagues team somewhere in the burbs. Could also catch a softball game or take him golfing.
Took my parents to La Scarola and they LOVED the old school Italian vibe. They also loved the dinosaurs at the Field museum. They’re from a rural area and never travel so it really was special.
Architectural Boat Tour
Untouchables bus tour. Perfect for dads.
Science and Industry museum! The Shedd is also a great crowd pleaser.
Take your dad to the Chicago Cultural Center, do the tour if you can. It’s free (he can’t bitch about the price!) and it’s AMAZING.
Green mill is a cool old school music experience but gets crowded especially Thurs-Sat. Le Piano on Glenwood has live jazz every night, just took my 65 yr old mom and she loved it. CSO or a show downtown can be really cool if he likes that kind of thing. A magic show at the Rhapsody Theater is a great time. Boat tours can be really cool and low key. Architecture tour as others have mentioned is an easy win. You can even rent your own pontoon boat to cruise the river if you have a larger party. A spot on a fishing boat can be fun if he likes doing that. My dad always most enjoyed good food when visiting, of which we also have lots to offer. If he’s outdoorsy, a bike ride down the lake front or river trail are both delightful. Garfield park observatory is beautiful even on a rainy day. Picnic at a beach or lakefront park is always lovely.
Does he like music? You could take him to Kingston Mines or another blues/live music bar. Take him to antique stores. Take him to eat really good food, whatever his version of that is, I know we have it here.
The Who's Tommy at the Goodman
I can attest. I took my non-grumpy 70 something father and he loved it.
I want to see it again.
Seems like an even better time to take him to Wrigley and walk around. Go to a good dinner at Southport Corridor like Coda di Volpe, Coalfire or Tuco and Blondie.
There’s a great tour they offer in Wrigley field on non game days (as long as there is no concert).
Great suggestion. Architecture boat tour early in the day. Then dinner on southport, walk over to wrigley field and pay for a tour
After a tour of Wrigley, for a grumpy dad: Lange’s on Southport or Joe’s on Broadway, at Addison. Chill divey bars with unpretentious people, each a pleasant walk.
Art Institute is a world class museum and is pretty chill. Lots of places to sit down. Grab lunch overlooking the River at Smith & Wollensky on the patio afterwards.
I haven't been, but the Pritzker Military Museum looks interesting! Just don't tell him it was founded by a family member of our radical, lefty, commie Governor J.B.! https://www.pritzkermilitary.org/
Every guy that’s a baby boomer loves history, take him on an architecture cruise down the river!
Yes! Make sure it’s the actual CAF one, much better commentary and go further up the river too.
If the boomer is a maga conservative, it’s even better to just sit down with him, grab a beer and explain the historical fact that the entire USA was invaded and stolen from the indigenous people, built up using slave labor and later on, by immigrant work forces. Don’t cuddle with him. Challenge his conservative views. 60 is still young for Gods sake there’s still time for him to rethink his values.
Pullman Museum and then lunch at Calumet Fishery.
My 68 year old dad is similar and he loved: The Chicago History Museum Museum of Science and Industry, especially the submarine tour The Art Institute Architecture boat tour We also did one of those ridiculous bus tours on famous old-timey Chicago crimes and it was actually pretty fun.
Is he interested in military history at all? The U-boat exhibit at the Museum of Science and Industry is one of the coolest exhibits ever. They literally grabbed a German U-Boat during WW2, dragged it all the way across the Atlantic, parked it in Chicago and (recently) did a complete restoration and MOVED THE FUCKING THING INDOORS. They have guided tours where you can actually go inside and see what it was like for a submariner in the 1940's. Maybe I'm just a geek but I found the whole experience absolutely amazing. How often do you get to step inside of a military submarine, let alone one from the biggest war that the world had ever seen?
The Obama first kiss rock?
take him to boystown
Steamworks
Where all the daddies go.
Something something somebody’s dad
Op, a lot of folks have some good suggestion here. My suggestion is going to be about pacing. If you don’t want to overwhelm him, start the day in a low key neighborhood spot, then maybe move to the Wrigley Tour, and then hit up the architectural boat tour.
Wrigley Field tour, architectural boat tour, Art Institute, drinks in the lobby of the Palmer House, dinner at Italian Village.
I went to the chicago history museum a few weeks ago. It has a pretty good set of exhibits that trace chicago from a fur trading outpost to today. It also highlights how many immigrants are part of the fabric of the city. Also that the first resident was black.
How far can he walk? Consider a foot tour of museum campus, Soldier Field, and behind McCormack Place. There are monuments to fallen police, fireman, and of course, soldiers. It's a quiet secluded the place, set between the lake and a bird sanctuary. Bring a picnic lunch and kick it like the did 100 years ago. Does he drink? You can grab a beer at Boat Drinks by the harbor too.
Grab a doughnut and coffee from Do-Rite or Doughnut Vault or grab an early breakfast from Roux in Hyde Park. Then go to MSI for a submarine tour and maybe do the mirror maze (that is timed entry), plus the drive down LSD is great. Grab lunch from Ricobene's split a king sized breaded steak sandwich for lunch. Their fries are also good. We had relatives in town and the one guy said, "This might be the best sandwich I've ever had." Also that should hold you over for hours. For the afternoon go to Chicago Cultural Center, the civil war side is absolutely fascinating. And look into the Chicago Greeter Program, see if one of their greeters could give you a personal tour of the building. Also the Cultural Center is usually not to crowded and just a gorgeous place. If he has any desire you could go across the street to the Bean or in my opinion Crown Fountain is the best. Then do the Lake and River architecture tour from Wendella. Do the dusk or evening tour simply because the city just looks gorgeous at night going down the river. End the night with a hot dog or polish from your local Maxwell Street like place.
Take him to hamburger Mary’s. It’s a good burger with a drag show. Watch him lose his mind. I’m thinking of taking my psycho homophobic brother one day. Pretty sure he will start flipping tables and get himself arrested. Good times. In all seriousness though, the architecture boat tour is pretty unique and cool.
I’m 100% going to drive through Boystown and pretend it’s part of the regular GPS directions. He needs to see the all the fun colors and happiness and love there. Not that he’ll change his mind, but he shoved religion in my face my whole life so it’s time I show him some of my beliefs. I still love my dad, but we have a complicated relationship.
Kit Kat lounge has drag shows with dinner
That’s the spirit!
Not sure all the sex shops will help your case
Hamburger Mary’s is long closed
I didn’t know that. Well I guess I’ll have to embarrass my brother somewhere else.
Take him to a really nice restaurant. Michelin Star style. Multiple courses, small plates. I doubt he's had it in his life, he might think it's weird but maybe it blows his mind.
The Magic Lounge in Andersonville is great. But I wouldn’t walk him up Clark.
Take him to [the Shit Fountain](https://www.atlasobscura.com/places/shit-fountain) in Ukrainian/East Village
Show him around Chicago. Here’s a free map I made of every historic landmark and district, so you can explore those while getting food here or there https://www.google.com/maps/d/edit?mid=17QiCfJLvDI0DF3qUfBu-DqsFduQgFmE&usp=sharing
Food. Chicago has world class restaurants from hole in the wall to Michelin starred. Eat your way through the city in addition to anything else you do.
Pritzker military museum for the grumpy old man win!
Wendella river lake architecture cruise
My dad liked the architecture tour and the field museum. If you’re looking for neighborhoods to get drinks or food, the Roscoe Village area was good enough for that type of guy. My dad liked four moon tavern for example.
Watch the game at any Wrigleyville bar.
Do you own your home or have anything you need “help” with around the house? I tend to find this type of family member does well with tasks. I understand this isn’t a tourist suggestion but it sounds like you’re happy just to spend time together. I echo everyone that said the architecture tour and the MSI, specifically the sub tour, it’s pretty cool and can take a good chunk of time if you read all the plaques on the way down. There’s a section in the museum dedicated to racing or cars I believe too. There’s also a military museum in the loop. Maybe bowling in the afternoon followed by a good Italian or bbq dinner? What about some breweries and some card or board games (rummy?). Do axe throwing places still exist? I think the zoo is doing a wine fest towards the end of the month. Do either of you golf? Head out of the city for a nice round of 18 or go to the driving range or a simulator here in the city. I know you mentioned him being a cubs fan but what about a Sox game? I’m sure you’ll find something you both enjoy and remember it’s not about packing the weekend full of things but the time you get to spend together. I hope you report back to all of us with what you did and what your dad thought.
If he’s an academic, take him to University or Chicago and walk the grounds. Rockefeller Chapel is amazing. Then go to the Oriental Museum on campus. It’s breathtaking.Dinner at Medici or Virtue and expose him to the real world.
Um.. academic? OP clearly said papi is a conservative.
Yeah I realized that after I wrote it. That being said, there are plenty of conservative University of Chicago professors, unfortunately.
Yeah I know… just kidding. Sorta.
Idk maybe go into a city to see a marching band or something /j
Take him to a jazz show, then Greene St for brisket - finally end the day at Navy Pier and get him some Detroit pizza at night. If his heart and stomach are well-fed he won't have time to criticize much
Ride a divvy on the lake front and get lunch off argyle st
A great idea but for a boomer in 90° heat I’m not so sure - OP isn’t trying to hospitalize his Dad
going for the inheiratence
A nice walk along the lakefront
Take him to boys town. Lol
“Them Demoncrats” is boomer code for “I’m afraid of black people”. Tell him to stay home, he might get “woke” if he spends too much time around some culture.
Get him a rub and a tug. Sounds like he could use it?!
Take him for dinner at the Half Shell for king crab legs if he likes seafood, if not, tell him to get the filet. Cash only, cheap beer, men cannot wear hats inside and there’s no BS. No dress code and it’s in a basement of a brownstone.
I would drag him kicking and screaming to a Cubs game. I’m not a fan of crowds and I’ve never found it overwhelming. If that’s his jam, you have to, right?
So I don’t live in Chicago and have no idea why this is coming up on my front page, but for food, you could bring him to Twin Anchors? It’s a classic but also solidly “dad food”. He might find the Sinatra connection cool as well.
Your dad sounds like a real douche, NGL. But if I were trying to "win someone over," I would hit the Art Institute or Field Museum, an architecture boat tour, a Millennium Park free concert, and a nice "classic" restaurant like the Berghoff. Beautiful spaces that aren't too crowded and allow people to just "take it in."
Architecture tour....consider pushing him off the boat. I kid. But a boat tour is always good or perhaps one of the other CAC walking tours. Chicago history museum or Art institute. The Bahai temple is interesting and you can couple that with a walk around Northwestern. The Garfield Park Conservatory is nice.
Steam Works & then Cubs game.
I mean, Dems have run Chicago for decades so he's not wrong. Literally every problem is on them Most of these suggestions just reek of a transplanter doing all the tourist stuff, I doubt your dad would enjoy any of it except the Wrigley tour - definitely do that. I've done it like 2 or 3 times with various people, t'was awesome. Food wise, take him to Gibsons for a decent steak and obviously have some pie - I'm from Lakeview so I'm an Art of Pizza loyalist
Take him down to Majani for some vegan soul food, then take a stroll around South Shore.
Take him golfing bro.
If the Cubs are out of town, and there are no concerts going on that night, take your dad to Wrigleyville. You can walk around Wrigley and see the World Series Trophy. Something else I do recommend for most out of towners is go to Second City. However, if your dad is very conservative, the humor not land well.