I am sorry to tell you this Samson, but you'd have to be crazy to commute from the city to Bolingbrook every day. I've done the long commute thing and in this city, especially when you are talking about dealing with I-55, it sucks.
We have an excellent Metra system to get you between the suburbs and the city. But the train schedule is only convenient for living in the suburbs and working in the city. Otherwise the train only runs once an hour or once every two hours. And there is the fact you have to find a way to get to the Metra station downtown from wherever you are living, and a way to get from the station to your work building. With a reverse commute, the train is not even be a viable option. So you will be forced to make that painful drive.
Chicagoland has some fantastic suburbs, many of them very close to Bolingbrook, with downtown areas and restaurants. When you want to hang out in the city, then you can make the drive. I doubt you intend on going clubbing every night of the week. To me it makes more sense to have a nice easy drive to work five days a week, and then only have to make the more difficult trip downtown every once in a while when you have a reason to go.
Then again, maybe I'm just a biased suburbanite.