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2022 Tours

SOLD OUT! Route 66 Adventure Tour June 4-12, 2022

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Waterfall Tour July 13-17, 2022

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Sturgis Tour August 6-14, 2022

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Around The Lake Tour September 8-11, 2022

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Rental Motorcycles

Want to take a tour on the latest and greatest Harley-Davidson technology? We have a fleet of rental bikes! Contact us for more information and rental rates.

Tour Testimonials

We booked our first Motorcycle tour with Mike and Kari the Trip around Lake Michigan! Beautiful routes. Very well planned out. A nice group of people that are now our new Harley family. We will definitely book another tour with Mike! Great memories!

Debbie Sammons Howie

Sturgis 2018, my first trip, had a great time, Mike Papp kept us on schedule, he did a great job and Ronnie was quick to care of all of all your needs, Don ran Clean up, also did a great job. A great crowd of riders, everyone was quick to help each other out and welcoming to make friends. I went into this trip knowing absolutely no one and made lots of friends . I would highly recommend Windy City tours.

Chris Ponce

We just retuned from the Windy City Motorcycle Lake Michigan Tour. My wife and I have traveled all over the world and this trip was without a doubt the best time we had. Jeff and Mike were outstanding and safe tour leaders. The hotels and food were great. The people in our group were all terrific. We are looking forward to our next Windy City Tour.

Steve and Marge Anzalone

Mike "Man Of The People" Papp

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