I used to fly that route on the guppy years ago and the commuters at the time painted a very bleak picture of the actual commute. Even though there are many flights - they were always full and delayed for t-storms in the summer and snow in the winter.

Didn't sound like fun. You may want to talk to as many people as you can about commuting on that route. Also, do a search (in the google box above) but there was crackdown on crashpads around midway and O'Hare within the last year and many were closed down.