@op Here's a list of recs I made for Vox on KTT1. Copy and pasted but added some more stuff.

general sight-seeing stuff:

-you can check out the boring s*** a la the Bean, but the coolest "popular" attractions are Shedd Aquarium and the Art Institute/MOCA.

-check out do312.com to see what's happening around the time you're coming.

-if you have the money and your trip lines up, please check out a Bears/Cubs/Sox/Blackhawks/Fires/Bulls game. they're super fun, even if you're not very into sports. baseball games esp are really chill with a couple friends

-if you're into records, stop by reckless.com. they've got a f***ton of stuff most of the time, and they also rotate more vintage/rare pieces in their collection depending on the store you go to.

for food/drink:

-Deep Dish, Tavern Style, and other Pizza: giordano's is overrated imo, but try it out. lou malnati's and pequod's s***s on them in deep-dish pizza. other recommendations include: Vito & Nick's (Ashburn), Fox's (Beverly), Pucci's (East Side), Beggar's (various locations), Rico's (Lansing), Marie's Pizza and Liquors (Elston) and Stephano's (also Lansing). If your pizza comes with a 1 liter of RC cola, you've hit a goldmine.

-ITALIAN BEEF. you need some, even if you don't think you do. Johnnie's Beef and Lukes on Harlem are my go-tos, but also check out Portillo's: It's the staple Chicago fast food chain. Keep in mind that you need to specify how "wet" you want the beef (how marinaded it is): "dry", "wet", and "dipped". I recommend either dipped or dry for your first one. also, choose what peppers you want: hot, sweet, or giardiniera.

-BREWERIES. Chicago is very well-known for its breweries. Revolution and Half-Acre are the kings. begyle, dovetail, maplewood, moody tongue are great.

-Burgers: Bad Apple, Small Cheval, Kumas Corner, BRGRBELLY, and Paradise Pub. I'm a fan of Kumas cause it's heavy metal-inspired.

-if you drink coffee, check out Ipsento. the people there are extremely meticulous and experts in making coffee. it's also a super chill place.

-if you somehow find yourself on the southside, I always tell people to go check out Imani's Original and get yourself some bean pies. They are absolutely delicious. She's also a total sweetheart if you catch her working there

for night-life:

-just stay around River North. if you walk around there are a f***ton of luxe bars and clubs. Lincoln Park and Wrigley are also good fun

if you're interested in fashion too:

Sahil if you into Southeast Asian stuff. really interesting stuff there, but it's niche af

independence has great workwear stuff, but you prob heard of them already

look around oak street, that's where a bunch of boutiques are located.

merz apothecary (lincoln square) for skincare/hair products/fragrances/general stuff.

for vintage stuff, check out Kokorokoko on n. milwaukee avenue. mostly 80's/90's stuff tho