If it is a weekend in June definitely use I-39
My earlier post:
The Kennedy Expressway (I-90/94) through Chicago will have lanes closed three weekends in June:
6/13-15 - for 55 hours all Eastbound lanes closed at Ohio/Ontario feeder. Eastbound traffic will use two temporary, 15 MPH lanes.
6/20-22 - for 55 hours all Westbound lanes closed at Ohio/Ontario feeder, detour will be on surface streets including a turn around!
6/27-29 - for 55 hours Eastbound Ohio exit (that handles all downtown traffic will be closed.
IDOT is predicting massive traffic jams on ALL area expressways. Detour routes are I-294 (toll road and heavy traffic any day); farther west on I-80 to I-355, also a toll road and pricy - $29.60 for a PU with a 2 axle fiver or a 2 axle MH with toad, higher for a three axle.
Personally I would recommend I-80 West to I-39 going from Indiana to Wisconsin or the reverse.