There are tons of hip places to go to, a LOT of them in the surrounding suburbs, from my experience. But you know, just stop and ask ANYONE for a reccommendation. I have yet to meet a ‘mean stranger’ there!

Heh, well, it’s no longer the twenties. However, there are plenty of clubs. I’m not a nightlife person, but Exit and Neo seem to be popular with the industrial/goth crowd. The Green Mill has jazz, if you’re looking for something close to the music in the movie, although it’s not that hopping. There’s a bunch of salsa clubs, too, I think.

I agree with Ignignokt in that times have changed, however, with the onset of retro-resurgence, themed places are still around. I hardly ever get to Chicago’s nightclub scene, but they are there. I think the smokey nightclubs are more exclusive and swanky (Frank Sinatra-ish) nowadays and not as easily found. There are so many bars/clubs, that it makes it hard for even an outside Chicagoan/Illinoisian to find the same!

I left Illinois in 1982, so please bear with me if I’m not up-to-date. When I was there, people talked about Rush St. in Chicago being wild. I remember going to a few bars in Rockford, where I lived. Not bad, but not great either. However, I was just 21 at the time – so I didn’t exactly have the voice of experience yet.

Kingston Mines is definatly one of my Favorites for Blues!
Rush st. is still pretty hot too.
Just really depends on what she is into though. For clubs you have Crowbar, SoundBar, Ontorage, and so many others right around that area. But then that is all the tourist places. Most chicago people don’t really go there.
There is a whole other city underneath the surface if you dig a little.

You can always take the Blue Line to Damen and hang out in Wicker Park. Like so many cool neighborhoods before it, Wicker was made popular by artists. Once the yuppies stormed it, though, most artists found they could no longer afford to live there. Still, you can go to Earwax (disregard the name) for something to eat, look at used books at Myopic, and go for drinks at … well, just about anywhere. If you want something a little less obvious, get back on the Blue Line and check out Logan Square. If you want a more ‘classic’ Chicago experience, however, I would strongly recommend that you check out the Green Mill up on Broadway. You can learn more about Al Capone’s old hangout at http://www.greenmilljazz.com/ if you’re interested. Even if you’re not a fan of jazz music per se, there’s a lot to be said for the charm and vibe of this amazing bar. Any more questions? Let me know.