I had to think on it to give you a good answer because that's honestly a hard question. So:

The two touristy things I always recommend are the Art Museum and the Architecture Boat Tour. To be honest every museum rocks (I especially love the Planetarium) and any sort of architecture tour is going to be great here. The River Walk is a neat little thing to see, and of course you can always walk the Mag Mile and Gold Coast for fancy shopping. There's also the two special towers (Hancock and Willis) which both have like, observation decks.

For less touristy things, walk through the neighborhoods! Wrigleyville, Boystown, and Wicker Park are all fun areas. Damen St and 18th St, are both nice little walk around areas. There is a Brewing District in the Kinzie area. The neighborhoods are just really neat to visit. Also, Chicago is multicultural so I always recommend visiting Pilsen, Greek Town, Ukrainian Village, and anywhere that has a ton of cultural shops/restaurants.

Finally, eat a lot of good food here. I can't even begin to recommend restaurants, but if it's not a chain give it a shot. There's also a great ice cream shop called La Michoacana that has a few locations around, if you're into that.

There are also a few kpöp shops around, but I only really recommend the one on South Kedzie. It's called KpöpAndMore, and it's run by a lovely Stäy 🩶

I'm glad you enjoy my fics, I promise there will be more soon!! Enjoy your time in Chicago!