Next Friday afternoon I will be leaving Detroit with destination Jefferson Wisconsin, which puts me into the Chicago area at rush hour. Any route suggestions?

You could take I-294 from the south burbs off I-80 as you will completely bypass Chicago proper. But it has 2 drawbacks. 1. It's a toll way, so you'll pay for the privilege. 2. It can get pretty congested during rush hour.

But all highways in the Chicago area get congested during rush hour. Be prepared to sit in traffic.

And  "rush hour" on a Friday is going to start earlier than other days.

OP's name is a bit ironic for this question.

A boat across Lake Michigan might be quicker

This appears to be a 6 hr drive? Leave earlier if possible.

If not, perhaps 94 > 80 > 355 > 88 > 39 is an option.

Earliest I can leave is 2pm eastern, which puts me right into the worst possible time to travel through there.

Thanks for suggestions so far.

I would consider my proposed route above. You should make up additional mileage in time saved.

Make sure your horn is in good working condition. If you want to feel like a local then you'll be using it a lot....don't be afraid to lay on your horn as soon as the light turns green - even if you are the 15th car in line. It seems to be SOP for there.

294 FTW.

294 north in the PM rush hour shouldn't be too bad. 294 usually runs heavy in the AM going north, and heavy in the PM running south, so you should be fine.

I'm OK with this.

Thanks, 294 is what I'm leaning towards.

HA,

I suggest having a dinner break before you get to the IN/IL border. The Borman Expressway is anything but what its name states it is. You might be better off driving further west to the I-355 extension, then going north. The tolls WILL cost you a ton, but welcome to Illinois, the most corrupt state in the union.

Earlier and slower.

I typically hang out at the office until 6:00-6:30 on Fridays just to avoid the mess.

If the earliest you can leave is 2 pm EST, what's the latest you can leave?  Do you have to be in Jefferson by a certain time?

If you leave Detroit at 3 pm EST, you'll get to the IL state line between 5:30 and 6 pm CST.  At that point, you'll be heading opposite of the heaviest traffic.  Yes, it will be busy, and sure, there could be a crash or three ruining the drive, in which case you're screwed.  That said, if you follow the Google maps suggestion of taking I-294 to I-290 to I-90, the only two real snags should be the ramps connecting those interstates.  At 6:30 pm, the traffic shouldn't be terrible.

Regarding the tolls, the Illinois Tollway system does have open road tolling for any barrier tolls, but even if you don't have I-PASS or EZ-Pass, you can still go through and pay the toll online within 7 days.

Unpaid toll info here

I have I-PASS, so I've never tried that feature.  If you don't want to tempt fate, you can always pay cash at the barrier tolls.  Just make sure you stay to the right to use the cash lanes.

As for the suggestions to take I-80 West to I-355, that is an option, but it always seems like traffic is bad on that stretch of I-80.

My advice: as you get closer to the Chicago area, tune in AM 780 for traffic reports on the 8s.  Google Maps has you taking "the Borman", "the Tri-State", "The Ike Extension" and "the Jane Addams".  Those should be mentioned in the second half of the traffic reports, as they always cover interior expressways first.

Good luck!!

Use the Waze app.

It's the best for the fastest routes through traffic.

https://www.waze.com/

You could take 80 all the way to 39, and take that up to 90. Extra miles but 39 should not be bad.

Waze (thanks for suggestion, had heard of it but never took the plunge) took me up 294 and it only sucked for a few miles. Traffic in Detroit was worse actually.

Thanks folks...