Hi all, I was awarded a summer legal internship on religious freedom with the St. Thomas More Society in downtown Chicago (on LaSalle St.). I will be in Chicago from mid-May through mid-August. I was wondering if anyone had a room to rent or knew of any good rental opportunities for those three months. If so, please send a PM here on the forums. I’m rated 2136 and happy to help out chess-wise as well or just to have someone to play with for fun.
Also, just looking for general comments about Chicago chess club activity. If on my own, I was told to prefer housing near the Wrigley Field area, but I won’t have a car for chess club access. I’m hoping to drop by the Open on Memorial Day weekend, but can’t commit yet since I don’t know what kind of schedule I’ll have.
Thanks for any feedback!
Ben Bentrup
With the exception of the Wicker Park Chess Club and the North Avenue Beach outdoor chess pavilion, nearly all chess activity in the Chicago area takes place in the suburbs. A few of us are working on changing that, but the fruition of our efforts is still a ways off. In the meantime, I’m a big fan of the Evanston Chess Club, which meets Tuesday evenings for open play and has a rated tournament every couple of months. You can get there easily by public transportation (Red Line to Howard, then 97 Skokie bus to Dodge and Mulford – about 40 minutes from Wrigleyville).
Hell, maybe I’ll just rustle up a little rated tournament to welcome you to town. 
If you live anywhere along the CTA Red Line train, you will have easy access to downtown Chicago (where you will be working), Wrigleyville, and the Chicago-Evanston border (Howard Street). From the Howard CTA station you can get to the Evanston Chess Club (a Saturday tournament every 2 months, informal play one weeknight per week) via CTA bus #97, or to Sevan’s club in Skokie (many tournaments and other activities) via Pace bus #290.
Also check out the Illinois Chess Association, including its calendar and its forums.
Major tournaments are often held in the farther-out suburbs, where public transportation is iffy. (Those trains and buses may not be close enough to the playing site, and/or do not run enough hours on weekends to be useful for chess players.) For example, this year’s Chicago Open (Memorial Day) is in Wheeling.
Good luck this summer!
Bill Smythe
My office is three blocks away from the Society’s offices: we could certainly get together for skittles.
A few blocks east from LaSalle, you’ll find the chess tables on the east side of Michigan (sometimes in front of the Art Institute, sometimes a block south, depending on the mood of the beat cop). For a few dollars, you can play skittles all afternoon.
But for serious chess, go to the Pavilion. It’s not gambling if you go there with the expectation of losing $20. (And yes, I’ve done that.)
Thank you all for the wealth of information in these wonderful replies.
What is the going rate for games there now? Back in the early 90s, Angelo Young tried to get me to play him there by splitting a series of $2 games with me. I took my leg out of the trap before he could close it. 
If you bring equipment and a good book–tactics and endgame studies are good ice-breakers–it’s easy to find a good game “for free.”
This is the Windy City: sets should be weighted, bring your heaviest vinyl board, and maybe some flat stones to hold down the corners.
I passed a few enjoyable hours at the Pavilion on Saturday chatting with a few, and playing a couple of 15 minute games with an old Serbian (past-his-prime) master, taking 1.5/2 where I’m pretty sure we both played like B-players. I’ll probably try to find some of these other clubs in the next couple of weeks. Loving Chicago: weather here > weather in Florida for May/June at least.