Reservations Rally Packages Route 66 Packages

Welcome to Chicago's largest Authorized Harley-Davidson Rental Location - Windy City Harley-Davidson Authorized Rentals.

Not all of us can afford to own a Harley-Davidson motorcycle. But that doesn't mean we still can't experience the power of a 103 cubic inch engine or fulfill our dreams on American's best roadways. Renting a Harley-Davidson is easy and a great alternative to owning a bike. With an Authorized Harley-Davidson Rental you will always have a new bike with low miles, featuring the latest technical advancements and performance upgrades. Each inspected by our own Factory trained technicians, cleaned up and ready to ride.

Rates for Harley-Davidson rentals are remarkably affordable, especially when taking advantage of our weekday specials & promotions. Rentals are available locally or for one-way destination tours. We specialize in both guided and self-guided tours to Sturgis, SD and Los Angeles (Route 66). Rentals can be packaged as a one day, three day or weekly rental period and to any size group.

We also offer guided tour experiences to destinations like: DAYTONA Bike Week, Route 66, Pier to Pier, the Sturgis Rally and the Tour around Lake Michigan - the Circle Tour. Check out our TOURS website at:

To rent a Harley-Davidson you will need a couple of things:

  • A major credit card to reserve your bike and guarantee your first model choice
  • $2,000/$1,000 available balance on the credit card, as a "security authorization" during the rental period
  • Riders must be 21 years old with a valid driver's license with motorcycle endorsement.
  • Enthusiasm and passion for he open road
  • Helmets are required, and provided at no charge if needed. Both rider and passenger must wear a helmet during the rental period.

You may find that the hardest part is choosing which Harley model you want to rent! Call the rental hotline at (708) 387-8750 let's ride!