Travel around/through Chicago?

Went through there in a car a couple of years ago, the 355 route if I recall. In addition to the chopped up surface for construction the lanes were very narrow, aggravated by the frequent lane shifts for construction.

I wouldn't have been happy if I'd been in my MoHo that trip.

Another vote for 80/39, which I've also done three times.

Spend forty four years driving all the roads in and around Chicago. I80 to I39 is your best bet. Westbound best to hit Ilinois after morning rush 10:00 to 2:00. Eastbound isn't that bad before 2:00.
There was westbound construction last fall westbound and you had to exit south on I65 go down to the next exit and make a cross over northbound a nd then exit west on I80-94 ramp.

294 is in fairly decent shape as far as road conditions go. 90 and 94 not so much. 80 has some bad sections westbound from IN but is in pretty good shape. 39 north of 80 has had quite a bit of resurfacing done in the last couple years. As I mentioned earlier, the entire length of 355 is being resurfaced. "Rough Grooved Surface" is how they describe it.

We went through Chicago last year with a 40'DP pulling a Jeep. I don't mind traffic, but the whole Chicago area is full of toll roads, toll bridges and has the worst road conditions that I've seen in a long time. I bet them haven't put a penny of the tolls into the infrastructure since they were built.

Steer way clear if you can.

Bill

80, 90, and 94 all come together near Gary, IN. 90 and 94 split off and both go through downtown Chicago. I would not consider taking either in a motorhome except maybe at 3:00 AM or 4:00 AM. 294 gets you around downtown, but takes you right by O'hare airport and the associated traffic. You could continue further west on 80 and take 355 north. Gets you further away from city traffic. Biggest issue is that 355 is under construction for the entire length (resurfacing, but still moves at 60 or better). 355 and 294 are both toll roads and will work with EZPass. 80 to 39 keeps takes you through lots of farmland so minimal traffic. Will add about 100 miles to your trip but gives you minimal aggravation.

I would take the 294 or 355 route. Have done them both in my motorhome with towed.

IMHO neither one is a great alternative. I try to give Chicago a wide berth if I can manage it. (On the other hand, I-90 is far superior to going on the surface streets, many of which ban large vehicles.) I-80 to I-39 would be my choice in that area if going somewhat near Chicago.

More generally, I prefer to go through Michigan, probably going through Ontario from Niagara Falls towards Flint, and then either take the SS Badger from Ludington to Manitowoc (not inexpensive, admittedly) or go up to the upper peninsula and take US 2 across towards wherever. The upper peninsula doesn't get one back to I-90 very readily, but depending on where you're going I-94 or US-2 may be viable alternatives heading west.