Skipping I90 Chicago route going from MA to SD

Here is what I would do, and I've done it. From the east take 80/90/94 west around the south side of Chicago, Take 294 north towards Wisconsin, get on 355 north to I90, take I90 west towards Rockford and then north into Wisconsin. Take I90 all the way to South Dakota.

There is a little constuction as always on the way to Rockford. Some may say to take 88 from I294 all the way to I39 and go lorth to Rockford, but I88 is ONE lane all the way from Aroura to Rochelle Illinois. You will lose much time there.