Originally Posted by Rosebud
Yeah, I love the art institute and it's one of my go to's, but I'm trying to think of what we can do that's a little more atypical, she's visited before and I showed her the big sights and while her friend's never been I'm trying to think of something cool to do in some of the more hipster parts of the city, neighborhoods like Logan Square, Wicker Park n Wrigleyville.
I would avoid Wrigleyville, I would never call it "hipster".
Are they beer people? I always enjoy The Map Room and nearby is Revolution Brewery which is nice. People always tell me to go to Skylark at Cermak and Halsted. It's in the South Loop/University Village area.
The Hungry Brain is a pretty cool dive in Roscoe Village, it's like belmont and western I think (google confirms), they have live music some nights and sporadic improv or open mics.
Empty Bottle has shows almost every night, it's in Ukrainian Village, I think I saw they were having a Mayan End of the World show on Friday.
My roommates favorite bar is the Gold Star. It's a nice dive.
Also what's your budget like? Butcher & the Burger is fantastic and I prefer it to DMK and there is no crazy wait like Kuma's. Kuma's is a cool little place but people are now snubbing it because its become popular. Still a good burger, still a cool place, and I find all the waitresses attractive. Big & Little's is pretty good but I find it over hyped. That's in River North so not exactly super cultured.
I didn't give you any great spots that don't involve drinking or eating, but my brain isn't functioning at a high level.
Okay, Let me just link to the r/chicago guide.
I recommend Too Much Light, iO and Second City.