Being from the Minnesota/Wisconsin area, but living in Pittsburgh, we tend to drive through Chicago 2-3 times each year. The GPS and online mapping services suggest taking I-90 all the way through Chicago, taking the Chicago Skyway to the Dan Ryan to the Chicago Circle to the Kennedy Expressway to Rockford. While that route is indeed the shortest highway route in terms of distance, it’s almost guaranteed to be very congested with lots of traffic, and ends up being slower in the end compared to other routes.

Over the past five years of driving through Chicago a few times per year, we’ve decided that taking I-290 and I-294 is the best way to bypass as much Chicago traffic as possible, without increasing the overall driving distance too much.

Westbound Route Details – Heading from Indiana to Wisconsin, first you need to exit from the Indiana Toll Road (I-80W / I-90W) onto I-80W / I-94W, which is kind of a goofy right-exit-then-overpass-to-the-left sort of thing:

I-94W will peel off after a while and head North into Chicago. The transition from I-80W to I-294N is really easy, as I-80W has to exit and cross over to head further West, while you just stay in the center lanes for the curve toward the North.

The transition from I-294N to I-290W is somewhat tricky, and is usually the only place we encounter any traffic-based slowdown. It’s a silly right-exit loop-under, that sometimes gets backed-up a few hundred feet owing to the slow speeds on the tight loop. Merging with the I-290W traffic isn’t too bad.

After that, the transition from I-290W to I-90W is a standard cloverleaf loop, and it has some nice protected “feeder” lanes to make your merge really easy.

Eastbound Route Details – Heading from Wisconsin to Indiana, first you need to exit from I-90E to I-290E, which is a simple right exit, so there’s no picture here.

The transition from I-290E to I-294S is much simpler than the opposite-direction transition loop-around shown above, and is just a simple “keep right” sort of bump around the interchange.

The transition from I-294S to I-80E is trivial, as is the interchange where I-94E merges into I-80E. The only tricky bit remaining is near the Indiana state line where you merge from I-80E / I-94E onto I-80E / I-90E, which has a silly cloverleaf bridge thing.

Overall, a pretty easy route, usually with no significant traffic that would be easy to avoid.

There are definitely some tolls along the way, but I think all the Illinois toll plazas have open-road tolling, so get your EZ-Pass and save time and money. If you get your EZ-Pass from Pennsylvania (you don’t have to be a PA resident) and elect for paperless billing and connect your credit card for automatic reloading of funds, there are no monthly or yearly fees!