I live near where I-90 leaves MN. I haven’t researched the route in the Chicago vicinity.
Brian
IMHO, your best route is to take 90 to 294, then 294 around. Just try to hit 80/94 on a weekend going east, and NOT Sunday afternoon going west, and avoid 294, 80/94 at anything resembling rush hour. I’d recommend before 7 AM or after 7 PM. Hope you like trucks! Just no easy way around it.
The Kansas Turnpike recently switched to a similar system. You are charged in accordance to the mileage you have driven on the roadway. If you have a K-Tag or similar sticker, you are billed automatically. If you don’t, you’ll receive a bill in the mail and can pay online. No stopping to grab a ticket or pay a toll, like it was in the past. Using the sticker gives you a discount as well.
Big Brother is always watching us. Even more so now.
And no more having to go back and get a shitload of dimes.
Heh. We were never that advanced in Kansas. There were toll collectors at every exit. You took a ticket when you got on the pike, handed the ticket to the collector when you exited, and they told you what you owed.
Not sure if it is a tall-tale but I was told (a few decades ago now) that out east (NJ Turnpike?..not sure) that they did the bit where you got a ticket when you got on and then paid when you got off. The shitty part, I was told, is they figured out this would catch speeders too. They knew where you got on and off and there was a time stamp so it was trivial to calculate your average speed. If it was some amount over the speed limit you had to pay the toll and then also got handed a speeding ticket. As a result, you’d often see people pulled over on the shoulder to wait out some time before exiting.
This is correct for the Illinois Tollway system. While the Skyway accepts I-Pass, it’s a separate system – I rarely take the Skyway, so I can’t vouch for what they are doing these days.
The Illinois Tollway temporarily closed the cash lanes in March of 2020, due to COVID. Though the initial plan seemed to have been to re-open the cash lanes once the infection issue was no longer a concern, they changed the plan, and the cash lanes are now permanently closed. So, the only options now are an electronic pass, or pay-by-plate, as noted.
The East Germans did that too on the pre-unification highway which was the only connection between West Germany and Berlin (103 miles). Time check at (the only) entrance and (the only) exit. Too fast - not normally a problem (but there were sporadic patrols), but too slow - maybe you had stopped along the way (forbidden) and did some “spying”.
When the Kansas Turnpike opened in 1956, speed limits were 80 mph. That was extremely fast for that day and age.
My father was a traveling salesman and he swore Oklahoma did the same thing on the Will Rogers and Turner Turnpikes (which eventually became part of I-44.) I’ve also heard the same story about the Ohio Turnpike. I suspect the story had to be true somewhere, even if it was only a legend on other toll roads.
Side note: for many years the Rogers Turnpike had the largest over-the-highway rest stop restaurant in the world, so Dad would stop there, get gas, eat a leisurely lunch, and resume speeding the rest of the way,
I am resurrecting this semi-zombie as my trip is soon.
(reminder: trip from Madison, WI area (Oregon, WI specifically) to just east of Jackson, MI)
If it matters, we are travelling East on a Friday and West on a Monday
My car-mate brought up the possibility of going all the way down to I 80 – it is a detour but you miss most of Chicago. (well, still get the southern edge) I am wiling to drive extra miles (If I was going alone I would seriously consider going via the UP*)
Is I88 to 355 a decent compromise? less of a detour but does catch some of Chicagoland
Brian
* If I was going alone I wouldn’t need to go south to Oregon which makes the UP slightly less bad
** FYI taking the Badger (or fast ferry) was considered but also don’t make sense
If it weren’t for the 290/294 construction, the best way to get through Chicago would by 90 to 290 to 294 to 80/94. 80/94 around the bottom of the lake is hellish more often than not. Continuing south off 290 onto 355 to 80 would be a good way to avoid the 290/294 endless clusterfuck.
Not sure how best to avoid 80/94. Best to hit the area very early in the morning or late at night.
It sounds like the two routes you’re considering are:
1: I-90/I-35 south from Madison to Rockford; stay on I-35 south to I-80; I-80 east into Indiana
2. I-90/I-35 south from Madison to Rockford; stay on I-35 south to I-88; I-88 east to I-355; I-355 south to I-80; I-80 east into Indiana
If I’m correct, there probably isn’t much of a difference, time-wise or traffic-wise. The I-88/I-355 route can get you more traffic, as those both do run more through the Chicago suburbs, but it’ll depend on time of day. The southern section of I-355, especially once you get past its interchange with I-55, tends to be pretty quiet.
Agreed; you want to stay off of that section of 294. It’s been under construction for four or five years, and still will be for another year or two. It’s a mess.
Absolutely agreed on this, and there’s just not any other particularly good way to get around the bottom of the lake and into Michigan. I’ve driven that way three times in the past few months, and there’s construction, yet again, on the Indiana side of the IL/IN state line; even without construction, the amount of truck traffic on that stretch of road makes it always a chore. I think that @N9IWP will just need to steel himself for it being an unpleasant part of the journey.
The only other real option is I-90, but to take that, you essentially have to go through the city proper, in order to get to the Skyway.
Also, to note this:
Heading eastbound into Indiana, then northeast into Michigan, on a Friday in summertime will be particularly traffic-y, as a lot of Chicago-area folks go into lower Michigan for the weekend. (Going north into Wisconsin on I-94 or I-90 from the Chicago area on a summer Friday is similarly busy, for a similar reason.) The later on Friday that you’re going through that stretch, the worse the traffic is likely to be.
Apologies, but 35? Do you mean 39?
IS it EVER free of construction? 
Since he is heading S rather than into Mich, he could try going down 394 and then hope the Lincoln Highway - 30 - is moving across to 65. But usually best to just suck it up and take your medicine. The ONLY way we figured to beat the 80/94 headache is to hit it EARLY in the morning. Definitely before 7 - 6 is better. Or late in the evening - maybe 9 pm. Rather shoot myself in the head than hit it on a Sunday afternoon…
Sorry, yes, I-39, for both scenarios. I haven’t driven on that road often, but my experience has been that it’s usually fairly quiet, especially compared to any highways in the Chicago metro area.
I think he is going into Michigan:
Stupid me. When I saw Jackson MI, I thought Mississippi.
The address I am going to is in Grass Lake, MI though the place is on Goose Lake.
I use Jackson as it MUCH bigger and is close enough. And the route is easy once we are in Michigan — it is just the Chicago vicinity I am seeking advice.
Brian
80/94 into Indiana is usually a complete nightmare. But if you’re heading to Michigan from Wisconsin and you’re not cutting across the lake, you’re kind of screwed. If you can time it so that you hit the Illinois/Indiana border later at night, or very early in the morning, that will help.
Coming home, if you hit that area in the afternoon, or morning rush on a weekday, you will not have a nice time.
Honestly, I’m more often surprised at how light traffic has been my last few rides around the lake, about four R/Ts so far in 2025. And especially two where I was expecting multi-hours of delay back into Chi: Memorial Day afternoon and an evening four Sundays ago.