Either go west on Division to Orleans, make a left (south) and take Orleans south to the I-94 ramp towards Indiana on Ontario Street, go through downtown on I-94, and get on I-55 towards Midway around 22nd street, or

Go south on LSD and get on I-55 around McCormick Center. (This is probably better.)

Watch the news or listen to AM radio WBBM to determine how bad things are on I-55 south. It could be bad tomorrow. If your plane departs at 7 am you might be able to beat rush hour. The exit off I-55 towards MDW is Cicero Avenue. Go south (left).

Steve