I would pay any amount of money or spend any amount of time to not have to deal with a car in Chicago ever again. Traffic, parking, and inflexibility to just hop on a train or bus are killer.
A car in Chicago is hell (at my first apartment it was first come first serve parking on the side of the road, the second required a valet which was also annoying), and mass transit was also a pain in the ass, and that's saying a lot since Chicago has an excellent mass transit system.