Top 5 Motorcycle Touring Routes Near Chicago, Illinois (2024)

Aug 5, 2021

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Top 5 Motorcycle Touring Routes Near Chicago, Illinois (1)

Chicago is an American city that’s a cultural capital of international repute. Known for its giant skyscrapers, which crowd the banks of the Chicago River and Lake Michigan. The Sears Tower (now known as the Willis Tower) is one of the tallest structures in the world. Many other record-breakers (like Trump Tower and the John Hanco*ck Center) are located nearby. The stretch of shopping outlets inside the city’s “Magnificent Mile” is a classic example of contemporary American architecture. The next time you’re in the Chicago metro area, make your trip more memorable by hopping on a motorcycle rental and touring these routes.

1. Summer On The Rivers

One-day trip — 180 miles

Ranging from quaint farmland to cool waterside haunts, the Summer On The Rivers motorcycle route takes you on a 180-mile loop through the midwestern portions of Illinois and neighboring Wisconsin.

From Chicago, jump from the city to Schaumburg, a mere 30 miles (or half-hour ride) away. Join Route 72 and head west all the way through the towns of Genoa, Kirkland, Davis, Junction, and Byron. From Byron onward, continue on Northbound Route 2 through Rockford, to the Illinois/Wisconsin border.

Road signs will point you to South Beloit in Wisconsin. Take Route 151 (also known as 51) up to Janesville, Wisconsin, and stay west as you travel up river, past the large hill, Road Ranger, and Kmart. Next, make a right at the intersection of Routes 11 and 14. In order to loop back to where you started, take US Route 14 west to State Route 11, and continue west until reaching Spring Prairie, Wisconsin. Go south on Route 120 and travel to Lake Geneva (also located in Wisconsin). Keep south on Route 120 after it crosses the Illinois border—it turns into Route 47. Keep south on this route through Woodstock and Huntley, and when you get to Route 72, go east to get back to Schaumburg.

During the Schaumburg to Byron stretch, you’ll see miles of pasture and railroad tracks. Between South Beloit and Janesville you’ll enjoy beautiful scenery, including riverside houses, and folks enjoying themselves on the river (during the summer months of course).

Road quality is great and the ride is fairly easy even for less experienced motorcyclists. The curves and twists along the riverside portions of the loop are thoroughly enjoyable for the more experienced.

Fuel and other amenities are fairly evenly spaced along this route, so there’s no need to worry about running low on gas. Janesville and Byron all feature great little places to eat as well.

2. U.S. Highway 6

One-day trip — 33 miles

Begin this route in Woodville, Indiana, 47 miles or 55 minutes outside of Chicago proper. Ride from Woodville all the way to Walkerton. And if that’s not enough for you, Highway 6 goes all the way to Ohio and beyond.

This trip is fairly rural, with the occasional residential area breaking up the combination of country and cornfield. But the wide horizon this route offers is a wonder to behold and a welcome change of scenery from the concrete jungle of Chicago.

This stretch of pavement is about as flat as you can find, so don’t expect any exhilarating twisties or hairball turns. This is a two-lane highway covering an idyllic piece of midwestern countryside. There are a few gas stations and convenience stores in some of the small towns.

3. The Oswego to Starved Rock Run

One-day trip — 45 miles

If you really wish to escape the cityscape of Chicago, but are inclined to stay within the state, The Oswego to Starved Rock Run isn’t a bad way to log some miles through rural scenery.

Starting in the city, head toward Oswego, just under an hour (47 miles or so) away. At Route 34 (Ogden Avenue), pick up 71 South and ride to Starved Rock State Park.

The Oswego to Starved Rock Run isn’t challenging for new riders, owing to the fact that it’s a flat, two-lane road with very few traffic lights. However, after you pass Ottawa, you’ll notice the road gets a tad twisty and hilly for a few miles after Yorkville, but before reaching Starved Rock State Park.

Sights on this route include a fair bit of farmland, river views, an ultralight airfield, a go-kart track, and the stunning state park. Wildlife abounds, including plenty of squirrels, deer, wolves, turkeys, coyotes, raccoons, and possums. As always, it’s important to keep your eyes on the road and ride within your limit.

There are a few fuel stations spaced no more than a dozen miles apart each, and small town restaurants serve up some delicious and inexpensive meals.

4. Rock River Run

One-day trip — 42 miles

You don’t have to travel to Arizona’s Grand Canyon or Colorado’s Arches National Park to see some fantastical rock formations.

From the heart of Chicago head toward Rockford (a 1.5-hour ride). From Rockford, getting to the route’s destination in Dixon, Illinois is simple via SR-2 south.

The attractions on the Rock River Run are the midwestern trekker’s dreams: lots of small-town midwest vignettes and postcard-perfect riverside views accessible from tree-lined roads. Rock River itself, which this route follows, features some unforgettable rock formations and ravines. For those inclined to do some hiking, Lowden State Park and Castle Rock State Park are on the way. Perhaps the biggest attraction is man-made: Lowden State Park features a massive statue of legendary Chief Blackhawk, which sits on a bluff overlooking the waterway.

Many of the small towns along the way—Byron, Oregon, and Grand Detour among them—offer plenty of amenities.

This is mostly a flat, well-maintained two-lane road perfect for beginners. It boasts a few gentle curves since it hugs the Rock River.

5. Historic Route 66

Two weeks — 2,448 miles

A trip on the historic Route 66 is a bucket list motorcycle trip for die-hard riders. It’s certainly a haul. Over 2,448 miles and traveling across three time zones and eight states is nothing to scoff at.

Of course, you can choose between starting in Chicago and completing the route in a two-weeks, or make it more simple by riding along the stretch of Route 66 that covers Illinois. If you’re partial to the latter, the following list of tourist attractions is a must-read.

The Route 66 Museum in Joliet near the start of this route is a worthwhile stop. The Route 66 Hall of Fame Museum. It shows off portraits of each and every person who contributed to the highway’s original construction. The latter museum is located in Pontiac, which has its own reason for being a destination for tourists: Pontiac is so full of murals it’s known as “Mural City.” President Abraham Lincoln’s house and law office, now a chapel, is located in the state’s capital of Springfield and also sits on Route 66.

Illinois boasts three “Muffler Men," large statues that were once a common sight before all manner of tourist shops, service stations, garages, and restaurants. The Gemini Muffler Man at the Launching Pad Restaurant (now closed) in Wilmington is an icon of the route and not to be missed. The most famous Muffler Man along the route, Tall Paul (in Atlanta, Illinois) depicts a giant lumberjack holding a hot dog. Selfie anyone?

Top 5 Motorcycle Touring Routes Near Chicago, Illinois (2024)
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