I'll throw out a few venues for music-related interests. I'm not cool enough to know what's going on anymore but I used to spend time at the following places. Each of the venues can run a wide spectrum from really good techno on one hand to James Zabiela on the other, so you should check to see who is playing before wasting a night out : )
As I don't know either of your preferences I'll just throw out a shotgun approach. LavaLounge - recently moved to a new location. The old place was a great venue that wasn't afraid to book hard acid, etc. Haven't checked the new venue yet, although I hear they have a pretty fun Drum & Bass weekly. Tini Martini - used to have a nice thursday Techno night, haven't been there since T1000 was there about a year ago though. Empty Bottle - Small venue that books great acts, Isolee, Dabrye (Tadd Mullinix), things like that Smart Bar - club in Wrigleyville, I live a few blocks away. Green Velvet will be there on the 16th, along with the techno buyer from the local vinyl shop (Josh Werner). They bring good acts (Rhythm and Sound, etc), but also book a lot of crap. Buyer beware. Sound Bar - Usually way too clubby. Richie, etc usually play here. Spy Bar - Also super clubby, but occasional good stuff. Caught a good Kill Memory Crash set there a while back, that sort of thing. Neo - The goth/industrial club in town, ranges from straight up industrial to brit-pop nights Delilah's - Psychobilly music on the last wednesday of the month. Holiday Club - great bar that has a pretty fun new wave/brit pop night every weekend. Little too heavy on the chart toppers, but I got them to play some Big Audio Dynamite so they can't be too bad, heh. Gold Star - little hole in the wall bar in wicker park, good stuff, free pool table in the back. [beware of hipsters] Inner Town Pub - another gem in ukranian village, one of my favorite spots Rainbow Room - not bad when it's not crowded [beware of hipsters] L & L - I frequent this the most lately, one of the only bars worth going to in Wrigleyville/Lakeview that isn't full of frat guys Gingerman Tavern - right next door to Smart Bar, good place to go before a show That's all I can think of for right now. As for chicago proper, go rent a bike, cruise over to the lakefront, and spend a few hours biking up and down the 20 or 30 miles of lakeside parks. Best thing you can do in the city. It's also a big city, so a lot of this depends on where you are staying and what your patience is for public transportation. -Arturo