Flychicaga, I respectfully disagree. I did my private at MDW and rarely had problems waiting on the ground. In fact, I've waited longer trying to cross 11R in Vero Beach! (sorry, FSI joke) In addition, my skills with the radio and more complex airspace helped me quite a bit when it came to the instrument rating. That being said, it does take about 10-15 minutes outbound and inbound in Class C airspace before you can start doing lazy eights or whatever... For me, the proximity to where I was living in Chicago was worth it. I'd rather fly 10-15 minutes to Lewis or Joliet than the hour or so to drive there (assuming traffic didn't stink!)
You just have to be careful of when you fly. There are certain times in the morning when everybody (airlines) is departing all at the same time. If you try and fly during those times, you'll probably have to wait. I never had to hold outside of the airspace. Once I had to do a 360 on final for 4L, but that's about it.
I would imagine that on a solid IFR day, trying to get back in might present some problems, but I have yet to experience that so I can't really say.
I'd have to say that it does something for your ego when you can tell your friends that you landed on a parallel runway to an ATA 757. (caution wake turbulence!)
I know it's silly, but still...
Anyway, the school that I have dealt with at MDW is now called Midway Aviators (formerly General Aviators) and their phone number is (773) 767-8100. Tell 'em Dave Lund sent you.
There are no schools at ORD.
But like you said, there are plenty of schools around the area. In fact, I just got a job in Palwaukee at
Airway Flight Services . If you have any specific questions about the schools, PM me and I'll give you my impressions of the ones that I visited while looking for a job.
What certificate/rating are you going to be working on?
Best of luck,
Dave