Chicago to Madison

148 miles
I-90 W to US-20 W to US-151 N

A one-tank trip doesn’t have to keep you in your own state. The drive from Chicago, IL to Madison, WI, is an ideal weekend road trip. Instead of taking the straight route on I-90, take a couple of detours to Wisconsin’s small, historic communities.

Along the way…

As you cross the border IL-26 N turns into WI-69 N. Get off in the little town of Monroe. In a state that is known for its cheese, Monroe is actually known as the Swiss Cheese Capital of the U.S. And they don’t just mean the stuff with holes…this is an authentic Swiss community that’s home to a number of cheese producers. In fact, it’s got a Cheese Country Trail, a 47-mile recreation trail between Mineral Point and Monroe (from Monroe, the Badger State Trail connects to Madison). Be sure to stop for a sandwich at Baumgartner’s, a local cheese store and pub.

Keep going on WI-69 N until you reach the town of New Glarus. Like Monroe, this town has one of the largest populations of Swiss-Americans in the country. With rolling hills dotted with farms, chalets, restaurants and festivals, it feels like an authentic Swiss village.  It’s home to the local favorite, New Glarus Brewing Company microbrewery.

Madison

Continue north to US-151 N until you reach Madison.  Wisconsin’s state capital sits between two lakes and is home to 40,000 college students and plenty of culture. Take the hour-long State Street Walking Tour for some local insight into the city’s architecture and history. Downtown’s Capitol Square is a must for great shopping and eating, particularly the Dane County Farmers Market. Ride a bike on the Capital City State Trail, which offers a 17-mile overview of the Madison area. At the university, don’t miss the 1,200-acre arboretum and the Chazen Museum of Art. There’s also the Frank Lloyd Wright-designed Monona Terrace and the Madison Museum of Contemporary Art.
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