Other caveats about the cheap Chicago theatre...
1. Most companies have a cheap performance on their schedule ($20), at the Goodman, it is the Sunday Evening performances, and at Lookingglass, it is the Tuesday 6:30 performances. I have taken advantage of both of these recently, namely The Clean House last summer at Goodman, and Argonautika (My #1 show [ANYWHERE!] for this past year) last week.
2. Steppenwolf has their 20 @ $20 deal where every morning they will sell 20 seats for $20 available day of show only.
3. Back to the Goodman, plays in the Owen (their smaller space) are general admission based upon level and are usually only $25 or $15. A friend and I saw Frank's House there a couple of weeks ago, and paid only $15 [and when it's @ playwrights horizons in a couple of weeks, that seat is going for $65!]
4. Heck, subscribe! 4 shows at the Goodman for $80, with the same seats at every perf! Plus more perks!
5. For the Broadway in Chicago stuff, there is usually some cheaper options as far as seats go [You can plan in advance as long as you're not picky about how far from the stage you are!]. I was in the Balcony for Spamalot and Martin Short Fame Becomes Me, and I never paid more than $30.
The one show everyone on Broadway is waiting to see: Twyla Tharp presents: Big Bottom - The Spinal Tap Jukebox musical!