My wife and I are headed out in a month. Touring Wrigley and going to a Cubs game on a Monday but basically have all day Saturday and Sunday to do different things.
I’ve been to Chicago a handful of times but have seemed to do the same things - Wrigley, Navy Pier, architecture tour, pizza, etc.
It's been a few years since I lived there but still go back often. Loved the food & bar scene there.
Wrigley is always a good time. If you want a different restaurant by the stadium go to Tango Sur which is a BYOB Argentinian Steakhouse. I think it is on Grace St. Cool place and good eats. Grab a bottle of wine at a nearby liquor store and enjoy.
I love the Architecture Tour and it is definitely a good one. But I can see it getting old. They are doing some Gangster/Mafia/Prohibition tours. Kinda fun to see where the Mobsters did what.
Here are some mainstays that most know about but want to make sure: Have you tried 2nd City or the Blue Man Group? Adler Planetarium? Museum of Science & History? Shedd Aquarium? Willis Tower or Hancock for drinks overlooking the city & lake? North Beach or Oak Beach?
I'd highly recommend one of the Helicopter Tours that go up the shoreline. Or one of the Kayak Tour on the Chicago River through downtown. Sailboat Tour on the lake.
If you like Craft Beers check out the Barrell Bus, which in itself is cool. Buzzes around Chitown hitting the microbrewery scene with samples on their tour.
Maybe go down to Buddy Guys to listen to Blues. Or Green Mill for Jazz. See who is playing at the Chicago Theater
I'm a food person so here are some of my favorites:
-Tango Sur - Argentinian Steakhouse mentioned above
-Carmines on Rush St - great people watching & Italian food. I use to help manage it along with a few other Rosebud Restaurants. Eggplant Salad is amazing.
-Dublins for late night drunk food & drinks. Open til 4am, 5m on saturdays
-Shaw's Crab House, Bob Chinn's Crab House or Joe's Seafood for Seafood
-Gibson's or Chicago Cut for Steaks
-Greek Isles for Greek food
-Italian Beef Sammies - Mr Beef, Al's or Portillo's
-Deep Dish Pizza - Gino's, Pequads, Giordano's, Lou Malnati's, Pizzeria Uno
-Pho Restaurants on Argyle St, lots of good ones there and can do that on the way to Wrigley
-China Town - fun to walk through and check out shops & restaurants
-Billy Goat Tavern - Chee Burger skit from Saturday Night Live based off of it
-Bar Hopping - go to Clark St, Hubbard St, Rush St or Division St. Variety of bars in each of those areas
-here are some of the newer Hip bars, haven't been to them
https://urbanmatter.com/chicago/chicago-bar-bucket-list/