Top Destinations for a Self-Guided Motorcycle Tour of Chicago, Illinois

Feb 2, 2022


Chicago, Illinois cityscape.

The city of Chicago, Illinois started as a small trading post at the mouth of the Chicago River and eventually grew to one of the nation’s largest cities. Home to the country’s first skyscraper, birthplace of the car radio, and the origin of the TV remote control, Chicago is a place with many notable “firsts.” This grand city also carries an important “first” for motorcycle riders who live to ride. It’s the starting point of “Historic Route 66,” which begins at Grant Park under the gaze of the Art Institute of Chicago.

Route 66, also known as US Highway 66, is the first highway to link Chicago to Los Angeles, California. After starting in Chicago, the route passes through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona before wrapping up in the Golden State. If you’re planning a ride to the Windy City, this roadway gets you to your destination with a maximum amount to see and do along the way. 

Before heading out, check out these Top 5 Destinations on Route 66 between Los Angeles and Chicago. If you’re simply looking for things to do and places to go once you’ve reached your destination, think of this as a cheat sheet for your self-guided tour around the Windy City.

1. Grandview Drive

Address: 3210 Grand View Drive, Peoria, IL

Route Length: 2.52 miles

Drive Time From Chicago: Two hours, 38 minutes in light traffic

Grandview Drive itself isn’t very long, but it is one of the most scenic routes in the state. According to President Theodore Roosevelt, this is the “world’s most beautiful drive.” A visit to Grandview is more about enjoying the beauty of the park and its various amenities. It’s complete with panoramic views of the Illinois River, stunning historic homes, and opportunities for hiking, picnicking, and more. You can easily spend the whole day here or simply pass through just to see what it’s all about. 

For this scenic ride, we recommend taking a Ducati for a spin. These motorcycles are built for everything from cruising to navigating tight hairpin-style turns, not to mention they’ve got serious curb appeal. If Grandview Drive is your plan for the day, or if it’s a stop along a longer route, a Ducati will have you covered.

2. Illinois River Road

Address: Check out their maps to find the ideal starting point 

Route Length: Depending on your interests, you can drive up to 291 miles along the Byway

If you’re out in Peoria, take the opportunity to drive along the Illinois River Road. Peoria is one of the communities along the Byway, but you can also take this route from several other communities like Ottawa, Havana, Canton, and Marseilles. This National Scenic Byway runs along the river and offers seemingly endless possibilities in terms of nature sites, canoe and kayak trails, dining, and other attractions. On the Illinois River Road website, you can find pre-built itineraries that cater to specific interests like railroad museums and military sites. You’ll also find their recommendation for a couple day trip in their Full Byway Tour. It connects 15 points of interest over 291 miles of road. For longer trips like this one, ride a BMW Motorrad rental. A BMW street bike offers an exciting, charismatic ride, smooth handling, and impressive German engineering.

3. Fabyan Forest Preserve

Address: 1925 S Batavia Ave, Geneva, Illinois 60134

Drive Time From Chicago: 52 minutes in light traffic

Located south of Geneva on the Fox River, the Fabyan Forest Preserve is an enchanting destination. Here, you’ll find a tranquil Japanese garden brimming with exotic plants like the Ginkgo Tree and Weeping Spruce. You’ll also see peaceful elements like the Moon Bridge, Tea House, and other iconic sites within this preserve. A farmhouse from the 1800s (once the home of the Fabyans) has been transformed into a museum where you can view various artifacts and original furniture. Plan to visit the Fabyan Forest Preserve on a Harley-Davidson rental from Chicago. Your ride will carry you effortlessly to your destination with the reliability and luxury expected from a good Harley.

4. Saugatuck Dunes State Park

Address: 6575 138th Ave, Holland, Michigan 49423

Drive Time from Chicago: Two hours, 10 minutes in light traffic

The advantage of riding from Chicago to Saugatuck Dunes State Park is in the ride around Lake Michigan. It’s not only a scenic drive, it’s a route full of alternative destinations. You can make a stop at one of Lake Michigan’s beaches earlier along this route or wander the marina in a nearby harbor town. We picked this beach in particular for its impressive sand dunes. While you’re exploring the area, you can stop in a picnic spot for some grub or take a hiking trail to really dial-in to the nature scene. Make your way along this route on a dependable motorcycle like a Harley-Davidson. These motorcycles practically speak for themselves, but we’ll always vouch for a Harley for a drive along this freshwater coast.  

5. Giant City State Park

Address: 235 Giant City Road, Makanda, IL 62958

Drive Time from Chicago: Four hours, 52 minutes in light traffic

Are you looking for a longer drive? Putting this state park on your itinerary takes you straight through the state as you make your way to southern Illinois. Giant City State Park is definitely the place to go if you prefer more in-depth nature experiences. You can go horseback riding, fishing, camping, and so much more within the grounds of this impressive natural marvel. 

For this nearly five-hour ride, settle into the comfortable seat of a BMW street bike. There’s nothing like a luxury motorcycle to make the longest trips an enjoyable experience. Take in the sights as you travel across the state without feeling the need to stop and stretch your legs every few miles.