self drive tour
Reservations & Quotes
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Reserve Today
# of People
# of Vehicles
# of Rooms
Departure Date
Desired Vehicle:

People Vehicles Rooms Price
1 1 1 $849
2 1 1 $899
2 2 1 $1349

 

*Tour pricing excludes Trike Rentals. Call our reservation department at 877-557-3541 for details.

Terms and Conditions

What's Included

  • All accommodations
  • Late model Motorcycle
  • Unlimited mileage
  • Helmets for the driver and passenger
  • Transportation between hotel and EagleRider location (restrictions may apply at certain locations).
  • Detailed day by day or hour by hour itinerary
  • Routing with scenic drive specific for motorbikes
  • Hotel Information
  • Tips for local areas
  • Sales tax
  • Environmental surcharge
  • VIP check-in at location

What's Not Included

  • Airfare
  • Food and snacks
  • Beverages
  • Fuel and oil
  • Insurance
  • Tips
  • Personal souvenirs
  • Parking fees, park entrance fees, road or toll charges
  • Seasonal surcharges
  • Rally surcharges
  • Transfer airport-hotel-airport

Chicago / Milwaukee Motorcycle Tour - Self Drive Motorcycle Tour

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!

None Chicago / Milwaukee Motorcycle Tour
3 Days / 2 Nights
Distance - Miles : 562 / Kilometers : 905 Seasons - Spring, Summer, Fall
Temperature : 50° to 90° F / 10° to 32° C
Reservations must be booked and paid in advance

Day 1 :Chicago - Milwaukee
Miles : 130 Kilometers : 209

Chicago / Milwaukee Motorcycle Tour

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.


Day 2 :Milwaukee - Madison
Miles : 155 Kilometers : 250

Chicago / Milwaukee Motorcycle Tour

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.


Day 3 :Madison - Chicago Departure
Miles : 277 Kilometers : 446

Chicago / Milwaukee Motorcycle Tour

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.