Chicago to Sheboygan drive: Best road trip stops, distance & time
The best stops on a Chicago to Sheboygan road trip itinerary are Six Flags Great America, Kenosha WI and Milwaukee. The distance from Chicago to Sheboygan WI by car is 148 miles, with a 2h30m driving time.
Planning a Chicago to Sheboygan road trip itinerary
The Chicago to Sheboygan drive takes you from the biggest city in Illinois to lakeside city in Wisconsin.
Our favourite thing to do in Chicago
The Chicago architecture cruise has a phenomenal wow factor, with the boat gliding between some of the world’s most legendary skyscrapers.
We found the commentary matches the views, too. Expect a fascinating run-down of the city’s history – and plenty of surprising detail about the buildings you’re seeing.
Chicago’s skyscrapers, music scene and massive collection of cultural attractions make it arguably the most exciting city in the US to visit.
Highly recommended Chicago experiences include an architecture river cruise, a gangsters and ghosts tour of famous Mob sites and a bike tour of the lakefront neighbourhoods. It’s also worth paying a visit to the Field Museum, the 360 Chicago observation deck at the Hancock Tower and the Chicago Architecture Center.
Sheboygan is home to the world’s tallest flagpole – the Acuity Flagpole is 400ft high. Other attractions include Bookworm Gardens, a botanic garden based around the theme of children’s literature, and the Breaker Bay Water Park.
Alternatively, you can try a Segway tour or spend some beach time on Lake Michigan. North Side Municipal Beach is the easiest to reach.
Chicago to Sheboygan distance and driving time
By car, the distance from Chicago to Sheboygan WI is 148 miles. That makes for a driving time of around two hours and 30 minutes. The quickest route is up the I-94 and I-43.
The best road trip stops on the Chicago to Sheboygan drive are Six Flags Great America, Kenosha WI and Milwaukee.
Chicago to Milwaukee drive: Six Flags Great America
Six Flags Great America is a theme park in Gurnee IL, with 12 themed areas. It’s a family-friendly theme park, but there are some hair-raising thrill rides in the mix. These include the Maxx Force rollercoaster, which features the world’s tallest double inversion, and the wooden racing coaster American Eagle. Several rides are themed on DC Comics characters.
Chicago to Milwaukee road trip attractions: Kenosha, WI
Kenosha’s main attraction is pretty clearly Lake Michigan. The HarborPark on the lakeshore is the best place to experience it, with a splash park and sculpture walk among the highlights.
The Civil War Museum is also here, and looks at the American Civil War from the perspective of the upper middle west.
Elsewhere in Kenosha, there’s the Dinosaur Discovery Museum. This concentrates on the link between dinosaurs and birds.
Best stops between Chicago and Sheboygan WI: Milwaukee
Milwaukee is famous for its beer, and doing a multi-brewery tasting tour is practically obligatory. Other good Milwaukee experiences include historical ghost tours and the Harley Davidson Museum.
You can also learn about Great Lakes history at the North Point Lighthouse and visit an art museum with a twist. The Grohmann Museum is devoted to art that shows the history of human work.
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