Best Motorcycle Routes in Illinois - Find Rides Near Chicago & Beyond

Jun 6, 2025

Illinois is home to nearly 150,000 miles of public roads, giving riders more access to long, open stretches than many states in the Midwest. While Chicago is the starting point for many trips, it’s the small towns, state parks, and riverfront highways across Illinois that really make riding here memorable. From quiet farmland to tree-lined stretches downstate, the routes in Illinois cover a lot of ground without needing to go far. If you're looking for motorcycle rides near Chicago, the roads just outside the city connect you to some of the most overlooked riding spots in the state. In this blog, we’ll highlight some of the best motorcycle routes in Illinois worth exploring.

Best Motorcycle Routes in Illinois

Here are some of our favorite motorcycle rides across Illinois, each with its own pace, setting, and places to stop along the way.

1. Great River Road Ride

Start: Nauvoo, IL

End: Alton, IL

View route map from Chicago

The Great River Road Ride takes you along the western edge of Illinois, following the path of the Mississippi River from Nauvoo down to Alton. It starts in Nauvoo, a small town with a lot of history tied to early religious settlements, and moves south on IL-96 through places like Hamilton and Kinderhook Township. The route keeps you close to the river for most of the ride and stays off major highways, giving you time to take in the surroundings without having to push through much traffic. Once you connect with IL-100, you’ll stay on that road all the way to Alton, which has a few good places to stop for food or stretch your legs before turning around or heading home.

It’s a ride that gives you some space and a steady pace without too many turns or confusing routes. The roads are well-marked, and the surface is generally smooth the whole way. There aren’t any tolls between Nauvoo and Alton, but if you're planning to start in Chicago, the full ride gets much longer, at nearly 300 extra miles, and you’ll need to use toll roads for part of the way.

2. Historic Route 66

Start: Joliet, IL

End: Lincoln, IL

There are a lot of ways to experience Route 66 in Illinois, but for this blog, we decided to create our own ride from Joliet to Lincoln. This stretch gives you a chance to experience some of the most well-known parts of the historic highway without taking on the entire state. It starts in Joliet and follows a mix of I-55 and sections of the old Route 66, guiding you through towns like Dwight, Chenoa, and Towanda before ending in Lincoln. While some parts of the route use the interstate, there are still plenty of opportunities to ride on the original roads that once made up the “Mother Road.”

The ride ends at The Mill Museum on Route 66, a small stop in Lincoln that’s dedicated to the history of the highway and the travelers who passed through it. The building itself is an old roadside diner, restored and reopened as a museum with exhibits, photos, and stories from over the years. It’s a fitting way to end the ride, especially if you’re interested in how Route 66 shaped travel across the Midwest. There are a few gas stations and food stops along the way, and the roads are mostly easy to follow without much traffic outside of the bigger towns. This route gives you a good look at what makes Illinois a key part of Route 66 history while keeping the ride manageable in a day.

3. Shawnee National Forest Loop

Start/End: Carbondale, IL

This loop through the Shawnee National Forest is a shorter ride, but it still gives you a good look at the southern part of the state. Starting and ending in Carbondale, the route follows IL-127 South and cuts through smaller roads like Pomona Road and 1st Street, making its way through the Pomona area before reaching the town of Anna. From there, it circles back north on US-51 and eventually reconnects with Carbondale. The roads are mostly smooth, and traffic is usually light, which makes it easy to enjoy the ride without having to push through busy stretches.

Along the way, you’ll pass through forested sections and quiet two-lane roads, with a few places to stop and take in the views or grab something to eat once you reach Anna. This ride is a nice option if you’re already in the area or want something more relaxed that doesn’t take up your whole day. Even though it’s on the shorter side, it’s still a solid loop that gives you time on the bike without being too far from town.

Want a Local to Show You Around Illinois?

Illinois has more riding variety than most people expect, from river roads along the Mississippi to lakefront stretches north of Chicago. Riders Share offers motorcycle experiences in Chicago led by locals who know the backroads, the scenic routes, and the stops that make a day trip worth the ride. If you'd rather follow someone who's done these roads than plan every turn yourself, a guided experience is a great way to see more of what the state has to offer.

4. North Shore Ride

Start: Chicago, IL

End: Waukegan, IL

The North Shore Ride takes you from downtown Chicago to Waukegan with a route that stays close to Lake Michigan almost the entire way. It starts on DuSable Lake Shore Drive and follows US-41 and Sheridan Road through lakefront neighborhoods, parks, and towns along the shoreline. The ride passes spots like Belmont Harbor, Tower Road Beach in Winnetka, and Fort Sheridan, giving you a few places to stop and stretch if you feel like taking a break. It's not a fast ride, but the slower pace works well for anyone looking to enjoy a day out along the water.

Once you get past Chicago traffic, the roads open up a bit as you move through towns like Highland Park and Lake Forest. Sheridan Road is easy to follow and offers a smoother experience than sticking to the busier highways. By the time you reach Waukegan, you’ve covered nearly 45 miles and seen a side of the North Shore that’s popular with local riders for a reason. This route works well for anyone starting in the city who wants to stay close to home while still covering new ground.

5. Kettle Moraine to Chain O'Lakes

Start: Woodstock, IL

End: Antioch, IL

If you're already riding up near Waukegan, it’s easy to keep going with a ride that brings you closer to the Chain O’Lakes region. Starting in Woodstock, this route moves east on IL-120 through McHenry before turning north onto N Martin Road and N Ringwood Road. It keeps you off the bigger highways and guides you through some quieter stretches on the way to Fox Lake. From there, the ride continues toward Antioch by way of State Park Road and Grass Lake Road, eventually reaching downtown Antioch just a few miles later.

This route isn’t long, but it’s a good way to link up a few popular areas in northern Illinois. Riders often pass through here when heading to or from Chain O’Lakes State Park, especially during warmer months when the area gets busier with outdoor traffic. The roads are in good shape for the most part, with just enough curves and turns to keep the ride interesting. It’s a nice follow-up if you’re already up near the lake and want to explore more before heading back.

Ride Through Illinois on a Motorcycle Rental from Riders Share

Riders Share makes it easy to experience some of the best Illinois motorcycle destinations without having to own a bike. With listings available across the state, including near Chicago and other major cities, you can choose from a wide range of motorcycles that fit your style and plans. Whether you're heading out for the afternoon or taking a full-day trip through the countryside, our platform connects you with bikes that are ready to ride. If you’re looking for motorcycle rides near you, renting through Riders Share gives you the flexibility to explore new places without the hassle of long-term ownership. Ride through Illinois on your own terms, with access to routes that might be closer than you think! 

Last Stop

Illinois has a lot more to offer once you get past the main highways. The routes we’ve covered here are just a few examples of what’s out there, and there’s always something new to check out. If you’re interested in riding through the city itself, take a look at our blog: Top Destinations for a Self-Guided Motorcycle Tour of Chicago, Illinois. It’s a helpful guide for finding your way around Chicago on two wheels while still making time for some interesting stops along the way.