2:00 AM on a Sunday would be the only time I would suggest driving through Chicago. There is no reason to go through Chicago on your trip. I80 is south of the city, it is the main cross country highway for truck traffic and is always heavy.
Timing is everything and you dont want to hit I80-94 westbound at morning rush which is 6:00 to 10:00 AM. There is one toll exiting to I80 from I294.
DW hates I80 because of truck traffic but we take it to I280 around the QuadCities then back on I80 to I380 N in Iowa to US20 west to I29 N to I90 At Sioux Falls W to Rapid City.
I think you would be better to cross at Windsor and avoid tolls on I80-90 they get pricey.
FYI Born and raised in Chicago. Retired Carpenter and drove every highway and byway in the Chicago SMA. Still have daughter living there so we run through twice a year.