Chicago / Milwaukee Motorcycle Tour

Self-Drive Tour 3 Days / 2 Nights
Tour Map
  • 515.0 mi = 824.0 km
  • Summer, Spring
  • 50.0 - 90.0°F = 10.0 - 32.2°C

EagleRider’s Chicago / Milwaukee Motorcycle Tour is a 3 day self-drive adventure through the most beautiful and exciting spots in Illinois and Wisconsin. On this tour you will get to ride through the exciting city of Chicago, tour alongside the shores of Lake Michigan, visit the famous Harley-Davidson factory in Wauwatosa, and ride to Fond du Lac, Wisconsin’s largest freshwater lake. The Chicago / Milwaukee Motorcycle Tour offers everything from big city life to small town historic charm. Book your next self-drive tour today!

Tour Itinerary

From Chicago you head north and enjoy a great ride along the shores of Lake Michigan. Cross into the state of Wisconsin and you are on your way to Milwaukee, a must for every Harley rider! Just a few miles west, in Wauwatosa, you can visit the Harley Davidson factory. Overnight in Milwaukee.
Continue your ride along Lake Michigan for a few miles out of Milwaukee and then you head inland. Your ride will take you across the Milwaukee River and by Kettle State Forest toward Fond du Lac, Wisconsin’s largest freshwater lake. From here you turn south and continue into Madison, where you overnight.
Pick up Hwy 151 and you ride via Mineral Point to Belmont, which served as the first capital of the Wisconsin territory in 1836. Cross back into Illinois and continue to the neat little town of Galena, a place that has change little since its 19th century heydays. From here it’s Hwy 20 all the way back into Chicago, where you return your motorcycle.
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