It depends on the weather. Most people are heading into the city, so it wouldn't be as bad as the reverse commute, but it wouldn't be a great commute. I wouldn't do it because parking sucks in the city and everything is overpriced.
I agree with John (+1 to you buddy)...find a place in Lake County or suburban Cook County, where things are a lot cheaper, less hectic, and less cliche. Des Plaines, Mt. Prospect, Palatine, Arlington Heights, Libertyville, Mundelein, Lake Zurich, and Barrington have mini downtown areas that are pretty nice.
Des Plaines, Mt. Prospect, Palatine, and Arlington Heights are not too far from a few EL stops, so you have easy access to the city.