5 Postcard-Perfect Midwestern Motorcycle Routes around Chicago (2020)
Chicago is one of those few American cities that truly is a cultural capital of international repute. Without a doubt it is the American city of skyscrapers, which crowd the banks of the Chicago River. The Sears Tower (now known as the Willis Tower) has long been considered the tallest building in the world, while many other record-breakers (like Trump Tower and the John Hancock Center) are located nearby. The stretch of shopping outlets in the city’s so-called “Magnificent Mile” is an early example of contemporary American architecture.
And although you wouldn’t be able to tell just from looking at the concrete skyscape of Chicago, the “Prairie State” of Illinois, neighboring Indiana and Wisconsin offer anyone on the back of a motorcycle rental midwestern stretches of scenery.
America’s “Heartland” is just as worthy of your interest and attention as Chicago, and we over here at Riders Share have cobbled together some of the best motorcycle route suggestions for you.
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 will take you on a 180-mile loop through the most midwestern parts of Illinois and neighboring Wisconsin.
If you think you’re going to rent a motorcycle in Chicago, simply jump from the city to Schaumburg, Illinois, a mere 30 miles (or half-hour drive) away. Next, get on 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 up 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 the river, past the large hill, Road Ranger, and K-Mart. 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 all the way to State Route 11, and continue west until you reach Spring Prairie, Wisconsin. Once there, 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’ll turn 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.
From Schaumburg to Byron you’ll see miles of pasture and freight tracks. Between South Beloit and Janesville you can enjoy beautiful scenery, including riverside houses, plenty of water sports, and recreational vehicles running through the water.
Road quality is great and the ride is fairly easy for even the most inexperienced of riders. The curves and twists along the riverside portions of the loop are thoroughly enjoyable for the more experienced.
Gas and amenities are fairly evenly spaced out 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. US Hwy 6
One-day trip — 33 miles
If you find yourself in the Chicago area and don’t mind hopping over the Illinois-Indiana border sometime in the summer or fall, then US Hwy 6 is your best bet!
Feel free to start this route in Woodville, Indiana, 47 miles or 55 minutes outside of Chicago proper. Just ride from Woodville all the way to Walkerton. And if that’s not enough for you, US Hwy 6 goes all the way to Ohio and beyond. Go as far as you like!
On this route you’ll find more or less completely rural countryside, with the occasional residential area breaking up the sometimes monotonous combination of country and cornfield. But the wide horizon this route offers is still a wonder to behold and a welcome change of scenery from the vertical skyscrapers of Chicago.
US Hwy 6 is about as flat as you can get as far as motorcycle routes are concerned, so don’t expect any exhilarating twisties or blind turns. This is a two-lane highway covering an idyllic piece of midwestern property. There are a few gas stations and convenience stores in some of the small towns you’ll pass on your way.
3. The Oswego To Starved Rock Run
One-day trip — 45 miles
If you desperately want to escape the concrete jungle of Chicago, but are inclined to stay within the state of Illinois during your stay, The Oswego To Starved Rock Run isn’t a bad way to get in some rural scenery and some natural beauty to boot.
First, rent a motorcycle in Chicago. Second, take a trip to Oswego, Illinois, just under an hour (47 miles or so) away. At Route 34 (Ogden Avenue), pick up 71 South and ride down 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 generally flat, two-lane road with very few lights. However, after you pass Ottawa, you’ll notice the road gets a little twisty and hilly for a few miles after Yorkville and before reaching Starved Rock State Park.
Sights on this route include a fair bit of farmland, river views, an ultralight airfield, go-kart track, and the absolutely stunning aforementioned state park. Wildlife abounds, including plenty of squirrels, deer, wolves, turkeys, coyotes, raccoons, and opossums. (Make sure you don’t hit any along the way!)
As for amenities, you needn’t worry too much— there are a few gas stations spaced no more than a dozen miles apart each, and small town restaurants serving up some delicious and inexpensive food (especially the restaurant next to the Amoco, as well as Grumpee’s Pork Chop and Chili Dog).
4. Rock River Run
One-day trip — 42 miles
First, make an 80-mile run from the heart of Chicago all the way to Rockford, Illinois (an hour-and-a-half drive). From Rockford, getting to the route’s end in Dixon, Illinois is a piece of cake! Just take the SR-2 south all the way down!
The attractions on this route are the stuff of a 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 truly unforgettable rock formations and ravines. (For those inclined to do some traveling on foot, Lowden State Park and Castle Rock State Park are on the way!) Perhaps the biggest attraction on this route, however, 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. Oregon’s sandwich shop The Cheese Shop is in Conover Square and a good place to grab a bite, as is Messies bar and grill (the best biker’s bar around).
This is mostly a flat, well-maintained two-lane route perfect for beginners. It boasts a few gentle curves since it hugs Rock River.
5. Historic Route 66
Two-Week trip — 2,448 miles
No selection of midwestern motorcycle routes near Chicago would be complete without a reference to Historic Route 66!
We understand that a route which some estimate could be as long as 2,448 miles and runs through 3 different time zones and 8 separate states can seem like a long drive. Luckily, you have a choice between starting your journey in Chicago and completing the route end-to-end in a two-week period of time, or simply staying along the stretch of Route 66 that covers the Illinois area. If you’re partial to the latter, the following list of tourist attractions is definitely a must-read for you!
The Route 66 Museum in Joliet near the start of the route is indispensable for any enthusiast, and the Route 66 Hall of Fame Museum will show you portraits of each and every person who contributed to the road’s construction. The latter museum is located in Pontiac, which has its own reason for being a prime 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 a total of 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. If you don’t grab a picture next to this essential piece of America, you can’t claim to have visited the Midwest!
Now that you’ve seen all that Illinois has to offer beyond the bounds of world-famous Chicago, we bet you’re just rearing to book a trip to the state as quickly (and cheaply) as possible. Riders Share has you covered—we have a wide selection of rides for rent, so we can meet your every want and need.
Once you rent a bike, you don’t have to worry about anything except seeing some beautiful prairies, and a whole lot more, in the Prairie State!