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Thats a tough call. I been through chicago many times. Mostly, without monty, I don't think I have ever got stuck for two hours. The exception being near the I-80 , I-65 interchange area but I was going with the rush hour traffic and that was some years ago during heavy construction in that area. I not sure when if ever I80 isn't under construction in that area. to some extent you will not face that the worst rush hour till on the north side. I would avoid I90 downtown for sure.
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