Def can depend on where you’re staying, but these are kinda all over the place things I’d say are good
Art Institute is def one of the top galleries in the world. If you’re an art person it’s a 100 you wanna do it.
If you want a deeper cut art museum-Wrightwood 659(even people who live here don’t rep it enough.)
People talk about the hot dogs(Devil Dawgs is the one I usually have), but the Polish Sausage at Jim’s Original is very much its own distinct vibe.
Fancyish vibes - Monteverde(Italian hard to get rez for but good) Kumiko(it’s in the top 25 bars in the world for a reason but also not fussy)
Day 2 Day vibes - Delilah’s, Goose Island(you said beer it’s at least local), Ming Hin(Chinatown locale), Charleston(gotta get at least one corner/residential bar in)
