Chicago has got the metra though which goes out to the burbs. I grew up about 20 miles outside of downtown in the burbs and the rush hour metra would get you downtown in half an hour.
You didn't have to go further than that. Suburbs to me only make sense once you have kids. I'm planning on moving back to chicago this summer and my girlfriend and I are looking to move to a triplex (currently looking at around ukrainian village/wicker park, maybe lincoln park) for a few years until we have kids and then i still might put it off until we have a 3rd or one kid reaches kindergarten age.