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EagleRider, the world's largest motorcycle rental, tour, and membership company, carries the largest selection of new Harley-Davidson, Yamaha, BMW, Honda, Indian, and more for rent and touring. All motorcycles are maintained to meet strict factory standards providing the most fun, safe, and affordable riding experience. EagleRider operates from over 200 worldwide locations, leads over 100 guided and self-drive motorcycle tours including Route 66 and the Wild West, and convenient one-way motorcycle rentals, luggage storage, free parking, free use of DOT-approved helmets, amazing Club EagleRider membership benefits, and more

Eagle Rider

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.

Arrival - Chicago, IL – Milwaukee, WI 

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&rsquo;s largest freshwater lake. From here you turn south and continue into Madison, where you overnight.

Milwaukee, WI – Madison, WI

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&rsquo;s Hwy 20 all the way back into Chicago, where you return your motorcycle.

Madison, WI – Chicago, IL - Departure

Late Model Motorcycle Rental

Motorcycle Friendly Hotels

Mobile Tour Guide App

Half-Shell Helmet for Rider and Pillion

Unlimited Mileage

Airfare

Meals except where specified

Anything not listed in “What’s Included” above

EagleRider's world famous Harley-Davidson Museum Motorcycle Tour is a Self-Guided Motorcycle Tour starting in Chicago and lasting 3 days.

Harley-Davidson Museum Motorcycle Tour | Self-Guided Motorcycle Tour

This tour can be modified to 2 days / 1 night for those who just need a quick getaway.

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! 

Transform your journey into an exhilarating Harley Tour by selecting one of our incredible Harley models such as the Harley-Davidson Electra Glide, Harley-Davidson Heritage Softail Classic, Harley-Davidson Street Glide, Harley-Davidson Tri Glide Ultra, Harley-Davidson Road Glide, Harley-Davidson Street Glide Touring Edition, Harley-Davidson Road Glide Ultra, Harley-Davidson Road Glide Tou, or for a different riding experience, choose from our sport touring models like the Triumph Bonneville T100, BMW R nineT Urban G/S, Triumph Scrambler.

Harley-Davidson Museum Motorcycle Tour

Self-Guided