Indie Chicago?

Of course, none of these indie places are within walking distance of Drupalcon on the Magnificent Mile. I recommend Phil's suggestions.

BLUES
- walk 3 blocks west (away from the lake) and one block north and find the RED LINE train at State & Grand. Take that towards HOWARD until you reach the FULLERTON stop (depaul university). Walk a block east to Halsted and go left/north a couple blocks and you will find Kingston Mines blues club and B.L.U.E.S. blues club for some late night soul!
The RED LINE is a 24 hour constant train and Depaul/Lincoln Park is a very safe area.

ALTERNATIVE/INDIE
- walk (south) down fancy Michigan Ave.until you reach Lake St., and walk a few blocks west until you reach the CLARK AND LAKE central train hub for Chicago. Take the BLUE LINE towards O'HARE and get off at the DAMEN stop. Art galleries, post-modern hip clubs and restaurants, record stores and music clubs are here, and notable artists such as the Smashing Pumpkins, Liz Phair, the Blue Meanies and the Smoking Popes are from this area. I love this area and live just up Milwaukee Ave. with the hipsters. This is the "High Fidelity" area.
The BLUE LINE is a 24 hour constant train and Wicker Park is always happening.

PUNK/METAL
If you are a fan of the edge, a trip to Kuma's Corner may be worth it. They serve humongous heavy-metal themed burgers in similar themed surroundings. I recommend the Pig Destroyer or the Metallica! It is on Belmont and further down the street are Bleeding Heart punk rock bakery, the Beat Kitchen, Schuba's (probably one of the better rock venues), and the Vic Theatre but these are rather spread out and are hit-or-miss. Directions are the same as BLUES, just go past fullerton to BELMONT.

CHINATOWN / REGGIE'S ROCK CLUB
Reggie's rock club is one of the better local venues for rock, and you can get there and see Chinatown too by taking the RED LINE south to 95TH and get off at the CHINATOWN exit. I've seen a couple of excellent shows here but it really depends on the tour. The Velvet Lounge jazz club is here too. Nothing else really musical or artsy around here though, it closes early.

JAZZ
If you've got plenty of time to travel, and looking for old time jazz, try the Green Mill jazz club in the Uptown neightbourhood.
Warning: this was Al Capone and the Mob's hang-out spot and people still get shot/smashed windows/report violence/? around here on a weekly basis and I'm not kidding. Also, panhandlers or crazy bums seem to gravitate to this area. But if you believe it is just isolated gang-on-gang or can ignore it, enjoy some swinging jazz in a historical joint!
Directions are the same as BLUES, just go past fullerton to LAWRENCE.

Division is too touristy and frat-boyish for me. Mother's is a good place to watch a game, that's about it. Wrigleyville isn't really happening this time of year. There's some local art and funky coffee shops and stuff in Hyde Park where Pres. Obama is from, but it's not a real haven. Pilsen has a nice growing art scene, a friend of mine is a sound engineer who lives down there, a free Mexican art museum during the day, but the jury is out whether you want to hang out there at night -- not yet "gentrified".

For a chance at real indie Chicago, catch the BLUE LINE to O'hare at the CALIFORNIA exit. You can wax poetic about literature with bearded pseudo-philospher-sun-glasses-at-night hipsters at Cafe Mustache, have a $2 Pabst Blue Ribbon with the rest of the skinny jeans wearers at Cole's, hit up the Dill Pickle for some save-the-earth vegan organic groceries like Tofurky and Aloe Vera butter, ride your bicycle in the snow and visit the Green party political headquarters, get all eighties with the ironically hip New Wave Cafe, and finish it off with $2 even slice of pizza from Big Tony's. Music consists of acoustic techno/dark-wave ambient noise groups in a back room of a dive bar or apartment. If you would be happy if every one was like Kramer from Seinfeld with facial hair, you should come here.
It's too indie and hipster-ish for me, but I can enjoy it is doses.. Popular and safe, though, in Logan Square.

Here's some areas you shouldn't go to at night:
Oprah's studio area
walking around the United Center (where the Chicago Bulls play) area
out to see the Garfield conservatory
trying to find the Goose Island beer brewery on foot

Welcome to Chicago!

It's good that Drupal is not such a suit-and-tie community that you can find artists, musicians, cooks, or others with a creative release or hobby. Let me know the time Sylvain!