Ah, the crown jewel of comedy in Chicago, and well deserved, at that. Second City launched the careers of hundreds of famous side splitters. If you’re going to hit one comedy show in Chicago, make it this one. There’s a reason that there’s a comedy school here and comedy scouts are frequent visitors. It's just that good.
A word of warning: The website is confusing. You’re going to see a whole bunch of shows to choose from and multiple theaters. The resident theaters are the Mainstage and E.T.C. (which stands for nothing, from what I can surmise). The Main Stage is the larger venue, with more broad-based improv, where you’ll see a revue or a “best of” style show, versus the more intimate E.T.C., which hosts more topical and satirical shows, like, say, A Clown Car Named Desire. At both venues, expect to share tables and rub elbows with your neighbors; seating is quite tight. UP Comedy Club, located on the third floor of the complex, is a third option. Operating in a more traditional comedy club manner, it brings in a rotation of stand-up and improv. If you can’t score a ticket to any of the above, you’re still in luck. Every night except Friday, Second City puts on a free improv show following its last performance. (It usually starts around 10:30pm, but check the schedule to see when the last show runs, and plan on the freebie starting 2 1/2 hours later). Note: Kids 10 and up are allowed at Second City, but keep in mind it’s a nightclub atmosphere and the language and topics aren’t exactly kid-friendly.