4 days
Difficulty level
1127 miles

Around the Lake Tour

Welcome to a tour around one of the most scenic routes in not only the Midwest but the United States.
The “Around the Lake” tour follows state highways around Lake Michigan (US’ second largest lake in volume and third largest in the area), through Illinois, Indiana, Michigan, and Wisconsin, hitting four of the most picturesque states in the Midwest. This tour will take you into Indiana along the Dunes Highway through charming small towns of Burns Harbor, Porter, and Chesterton. Cross over the Mackinac Bridge and ride through the forests in the Upper Peninsula of Michigan taking in the breathtaking views. Pass through Northeastern, WI hitting the home of the Green Bay Packers and riding in what is known as the Cape Cod of the Midwest,” Door Peninsula.

At the end of the four-day trip, you will ride just over 1.000 miles along the coastline of Lake Michigan visiting the homeland of Harley-Davidson at the world’s only H-D Museum in Milwaukee, WI. Reserve a spot now to experience an incredible Midwest trip on two wheels.

DEPARTURE/RETURN LOCATION Chicago – Chicago  [Roundtrip]
DEPARTURE TIME Please arrive at least 2 hours before tour start
VIP Hotel Check in Shared room in +3 stars hotel
Breakfast on riding days Gas on group riding days
Welcome packet/reception Tour book w/route description
Tour T-shirt & Patch Group photo/Tour photos
Water on riding days Follow van, door 2 door service
Tour leader/guide Farewell group dinner
Food & Drink
Motorcycle Rental
Optional attractions & Nat. parks
Anything not listed in “Included” above

“There’s something uniquely satisfying about touring by motorcycle. The enhanced sense of freedom and the heightened feeling of adventure as you sweep through twisties and curves. Join us for a once of a lifetime experience!”  


Day 1: Chicago to Mainstee, Michigan

(Driving day 1: 282 miles)

Kick off your adventure on two wheels at Illinois Harley-Davidson, riding 282 miles to Manistee, MI. We cruise into Indiana and follow the Dunes Highway through the towns of Burns Harbor, Porter, and Chesterton, before entering Michigan to enjoy a beautiful ride that takes you through many charming towns along the shoreline.


Day 2: Mainstee to Manistique, Michigan

(Driving day 2: 336 miles)

We continue to hug Lake Michigan through one of the most beautiful regions in the state. Today you will cross the Mackinac Bridge and ride through the dense forests in the Upper Peninsula of Michigan.


Day 3: Manistique to Manitowoc, Wisconsin

(Driving day 3: 330 miles)

Kickstands up in Harris, MI. It’s time to head to the dairy state. On day three you’ll ride to Manitowoc, WI checking off another 330 miles.


Day 4: Manitowoc to Milwaukee, Wisconsin

(Driving day 4: 91 miles)

On the last tour day, we will ride 91 miles to the iconic homeland of Harley-Davidson, Milwaukee, WI finishing out the tour at the Harley-Davidson Museum.

Note: This program is a guideline for activities and experiences on the tour. Deviations may occur, but we guarantee that our positive tour leaders will do their utmost to execute the program as described – as far as it is feasible and circumstances allow. We are continually working to improve the program, thus you may experience positive surprises.

Prices per person

2 pers / 1 bike / 1 shared room:
From $949
2 pers / 2 bikes / 1 shared room :
From $999
1 pers / 1 bike / 1 single room :
From $1 249
1 pers / 1 bike / 1 shared room :
From $999

Book tour

Tour category
Date from
Date to
Booking deadline

Tour category:
Around the Lake Tour
Date from:
21 Jul 2022
Date to:
24 Jul 2022
Booking deadline:
23 Jun 2022

Tour category:
Around the Lake Tour
Date from:
08 Sep 2022
Date to:
11 Sep 2022
Booking deadline:
11 Aug 2022

Tour Reviews

5.00 based on 2 reviews
October 31, 2020

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.

May 26, 2021

Beautiful trip 👍

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