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Last Saturday, a group of my friends and I decided to venture to Wicker Park for the night.  Jessica had found a bar called the Crocodile (1540 N Milwaukee, http://www.crocodilechicago.com/) that served free pizza with every drink purchase, so the plan was to start there, and then just wander around and see what was close by.
We enjoyed some fish bowls (diet Coke for me since I was driving) and the pizza .  You get one personal size cheese pizza with every drink, so everyone got their own pizza!
The service was good, and around midnight, it started to get crowded.  There is a downstairs basement area for dancing, which we had to wait in line for, that really isn't that great.  The best part is the main bar upstairs.  Our next stop was Debonair (1575 N Milwaukee, http://debonairsocialclub.com/), a bar right across the street.  I really liked the interior; it was black and white themed, and they had the new Alice in Wonderland movie playing on mute in four squares on one wall.  I thought it was very artsy.  There was a small dance floor, and the music was ok.  We didn't stay at Debonair very long and decided to make our way to Cafe Absinthe (1954 W North Ave, http://www.absinthechicago.com/).
It was very crowded, so we only stayed about 5 minutes- at least we could say we went in.  lol.  The final stop of the evening was Big Star (1531 N Damen Ave, http://www.bigstarchicago.com/).
This bar was very spacious and had cheap tacos, but unfortunately when we got there, they were no longer making tacos.  A pitcher of lemonade with bourbon whiskey and a cool breeze (I tasted a bit, and it was A LOT more whiskey than lemonade!) was a good way to end the night. :)

Overall, it was a fun night exploring a new neighborhood, but I wasn't really feeling the vibe.  The crowd in Wicker Park is a bit old for me, but I would definitely go back to Crocodile.