Chicago!
Hopefully a North sider will pipe up here, but I-294 / I-94 from I-90 north to the Wisconsin border or there abouts has been a construction nightmare all summer / fall. I don't know if they got it picked up, (I don't think so), but I think it is a multiyear project.
That said, I'd take I-90 through Chicago, don't stop on it though from the Indiana state line, until you get to I-294, there is some not so nice neighborhoods along the way!
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