Sometimes one does get lucky. I always have the expectation that driving through that stretch of road will be painful, and if it isn’t, then it’s a pleasant surprise.
While the northern sections of Chicago can be avoided the southern section is harder to avoid. I can’t imagine highway 30 is much better (almost as crowded and with stoplights). At least I’m not under time pressure.
Brian
You’re right; it’s generally not any better.
If you have access to Google Maps/Waze/whatever on a smartphone, or on your car’s nav system, I highly suggest using it, and following its directions if it turns out that rerouting is needed.
I regularly attend gaming conventions in Ohio; my usual route back home takes me up I-65 from Indianapolis to northwest Indiana, then getting on 80/94. I’ve had several instances in which Google Maps tells me to bail off of I-65 well short of the 80/94 interchange, and then zig-zag along county and state roads, crossing over into Illinois, and getting back onto 94 well past the state line.
does Kansas still time-stamp your ticket and then give you speeding ticket if you get to end too soon?
The Kansas turnpike went ticketless last year, so it’s all electronic. If you don’t have a K-Tag or other transponder, you’ll receive a bill in the mail based on your license plate. So presumably the Kansas Turnpike Association would know if you exceeded the speed limit between any two checkpoints along the way, but I’ve not heard of them issuing tickets well after the fact.
(Not to say the KTA wouldn’t do such a thing, especially to out-of-state cars…)
The Illinois Tollway started issuing transponders to tollway users 20+ years ago; when they first did this, there was a level of concern here that they could determine if a car was speeding, based on the amount of time it takes for its transponder to register at two consecutive toll-collection plazas. At that time, they issued statement saying, “we have no plans to issue speeding tickets based on transponder data,” and AFAIK, they never have.
I’m pretty sure this is an unfounded rumor about every toll road that uses/used a ticket system.
no it actually did happen to me when driving cross country
I realize that with the possible exception of 4AM traffic will be bad around Chicago. Is it slightly less bad at say 11AM vs 9 AM? My carpool buddy is not an early riser so if we aren’t leaving Madison at O dark 30 is there a less awful time?
Brian
Generally, yes. At 9, you’d still be fighting the tail end of the morning rush. However, there’ll still be quite a bit of traffic – especially truck traffic – at midday, particularly when you get close to the IL/IN border, and across into northwestern Indiana on 80/94.
Midday is likely to be less terrible than during rush hour, but still likely to be busy. Later in the day, on a Friday afternoon (since I think I recall that that’s when you plan to make the trip), traffic will get heavier again, due to not only rush hour traffic, but the exodus of Chicago-area people who are going to Michigan for the weekend.
I thought they all headed to Door County 
We will likely leave Friday morning for the Eastbound leg.
Monday morning for Westbound.
Brian
If you hit the Chicago area mid day - say 10-2-ish, just don’t plan on making time. It will move, just with plenty of slow-downs and the occasional stop. It will likely FEEL much worse than the actual time added to your trip will prove.
The exception, of course, is if there is a significant accident or some other stoppage right on your path. So try to use whatever tech will help you identify those.
To some extent, we might be overstating how bad it is. I mean - it sucks that you might be going no faster than 40, with an occasional stop. But unless you are - say - heading into the city right before a Bears game, traffic will move. Just slowly.
Last Friday I took 294 north. The stretch north of Roosevelt/290 looks to be essentially done. The 290/294 interchange and 294 to the south will still take some time.
In Oct, I’ll be heading around the lake to Mich. I’ll be leaving around 10-11 a.m., and will take 294 to 80/94. Just will add an extra half hour or so to my intended travel time as opposed to if I were going th espeed limit.
Are you sure you don’t just want to sail across the lake?
Half go to Wisconsin (either Door County or “up north”); the other half go to the lower peninsula of Michigan.
Well said.
Especially if the OP and his friend take the more westerly route that was described a week or so ago (39-88-355-80, or 39-80), it’s likely that the “worst” part of the drive will be the last few miles on 80/94 in Illinois, and the first 10-ish miles in Indiana. And, if you’re hitting it mid-day, “worst” may well be “slow but moving,” as opposed to “stop and go for 15 miles.”
Yup. The 294 project is pretty much done from North Avenue, north past O’Hare, to the I-90 interchange. The southern end of it (south of the “Mile-Long Bridge,” which is just south of I-55) is also pretty much done. The middle section, especially the area around the interchanges with 290 and 88, is still a disaster most days and evenings.
I’d avoid the region during the peak rush of 7-9am & 3-5pm or so but take the shorter path, 90 through the Loop and take the Skyway, no other strategies, longer-route shortcuts, etc.
Even on 294/tristate, I think it will be the more interesting leg of the journey. I live & work near ORD and drive around a lot and still get a kick out of the local sights: the airport, the railyard, Ryne & Urlacher, Topdog, Butterfinger, cool peeks at the skyline.
Those “sights” probably feel like home to you, but 294 (especially from ORD south) really isn’t a scenic road, by any stretch of the imagination, even when it’s not under construction. It goes through a lot of industrial and light-industrial areas, has a metric crap-ton of billboards, and when it’s cutting through residential suburbs, either side of the road is usually bounded by high barriers to block sound, so you don’t see anything other than those walls.
Plus, half of what you describe as '“local sights” are billboards and commercial signs. “Look, it’s the fifteenth billboard for hair restoration, featuring a bad pun, that we’ve seen in the last five miles!” 
The OP isn’t coming to visit Chicago; he’s interested in the least-painful, least-time-consuming route to get through or around Chicago, in order to get to his destination in Michigan. If 294 weren’t under construction, it might well be the fastest route for him (depending on time of day), but that’s not the case these days. I just drove past the construction area on 294 about ninety minutes ago (i.e., around 1:30pm), and the southbound traffic was crawling.
Subjecting the OP to that traffic for “local sights” is bad advice, IMO.
My brother lived in Ypsilanti for 4 years and when he had to visit family in Wisc, drove South to I-80 and then west to 39 north. He hated Chi-town traffic. One time he tried to go North over the UP and hit a deer on his way. Never took that route again. I live in Cinci and use my EZ Pass to take 74 west to Bloomington and then take 39 North picking up the 90 in Rockford
It seems like you want to scold to scold me for the Tristate billboards but I recommended the Kennedy.
I only meant the Chicago area will be the most interesting leg of the trip, regardless of route. I’m sorry you don’t like railroad operations and chocolate bar factories. Some of us need more stimulation than Redamacs and Belvidere Assembly Plant. But less than Krazy Kaplans, sheesh, they try too hard.
I’m not intending to scold you; I’m just noting that “look at some billboards and a brief view of the airport and a big railroad switching yard” is probably not worth a longer delay, due to that construction zone, for the OP, who is, again, trying to get to a vacation destination with as little hassle as possible as he circumnavigates Chicago.
It’d be different if that route was actually scenic, but I think that most people wouldn’t consider it to be so. It’s flat, it’s highly built-up, and the things which you find “interesting” about that stretch of road probably wouldn’t be considered interesting to most people, especially ones who aren’t from the Chicago area.
For the record, I’m a big train nerd, and I always glance at that Bensenville switching yard as I drive southbound on 294 (which I have done literally hundreds, if not thousands, of times).
When I worked near the la Crosse rail yard* I certainly looked.
But for this trip I am trying to get to near Jackson, MI with the least amount of frustration.
I actually have driven to ORD to on the way pick up an attendee – I don’t remember it being awful but it was quite a while ago so maybe I blanked the bad parts out.
Brian
* I’m sure very small compared to Chicago, but big enough that La Crosse is on several railroad board game maps.