Road Trip Itinerary From Madison, Wisconsin to Chicago, Illinois

Total distance (approximate): 285 miles (459 km)

Total driving time (approximate): 5 hours 56 minutes

Recommended number of traveling days: 3

Distance: 40 miles (64 km)

Travel time: 55 minutes

Devil’s Lake State Park is a natural oasis just under an hour’s drive away from the state’s bustling capital. Wisconsin’s biggest state park, visitors can enjoy sitting along the glacier carved lakeshore, admiring the stunning quartzite bluffs, or the more adventurous can rock climb or go for a hike around the park’s 9,000 acres. It’s best to head there early in the morning because the park may close early depending on the season.

Distance: 42 miles (67 km)

Travel time: 53 minutes

The House on the Rock in Spring Green is one of Wisconsin’s most unique tourist attractions. The goal of its creator Alex Jordan was to create a house as awe-inspiring as the view from where it sits. The location now also includes additional buildings and exhibits, including the world’s largest carousel. After a long day of traveling, turn in for the night at the House on the Rock Inn or Resort.

Distance: 41 miles (66 km)

Travel time: 52 minutes

New Glarus, Wisconsin is a small village with a lot going on. Founded by a community of Swiss immigrants in 1845, New Glarus has held on to its heritage and is now the best known Swiss settlement in the USA. Charm from the old country can be found in the traditional meat markets, bakery, and restaurants in the downtown area. The city’s craft brewery is one of the best in the state so be sure to enjoy a pint of Spotted Cow before you go.

Distance: 73 miles (117 km)

Travel time: 1 hour 33 minutes

Lake Geneva is a small resort town in southern Wisconsin where you can relax in one of the local spas, take part in a zip-line adventure, or enjoy a romantic stroll along the lakeshore. Enjoy a tasting from the local winery and take in your beautiful surroundings.

Distance: 28 miles (45 km)

Travel time: 36 minutes

Located along Interstate 94 on the way to Chicago, the Mars Cheese Castle is a Wisconsin landmark. While this famous store specializes in cheese, you’ll also be able to pick up sausages and Wisconsin souvenirs here. Don’t be surprised if you bump into any famous faces here – the likes of John F. Kennedy, Johnny Cash, and Joe Biden have all made pitstops at the cheese castle.

Distance: 62 miles (99km)

Travel time: 1 hour 5 minutes

While the drive from the Mars Cheese Castle to Chicago might not be the most interesting stretch of highway, there are plenty of places to stop if you want to move around or grab a bite to eat. The Illinois Tollway Oases offers a large selection of restaurants and free public restrooms. Those hoping to get a little shopping in before their trip is through should visit the Gurnee Mills shopping center, and while in Gurnee, Illinois, thrill-seekers may want to catch a ride on one of the many roller coasters at Six Flags Great America.