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

Jun 2, 2025

Here’s something most people don’t know: Illinois is home to the start of the iconic Route 66, and it kicks off right in downtown Chicago. That means some of the most historic Chicago motorcycle routes are hiding in plain sight, just a few blocks from the city’s biggest landmarks. From skyline views to forest preserves and scenic river rides, a motorcycle tour in Chicago can surprise you with how much there is to explore beyond the traffic. In this blog, we’ll highlight some of the best places to ride around the city and give you tips for planning a self-guided route that actually feels worth the ride.

Tour 1: Starved Rock State Park

Start: 2668 E 873 Rd, Oglesby, IL 61348

Distance From Downtown Chicago: About 90 miles southwest

Fees and Permits: Free entry; parking available on-site

Starved Rock State Park is one of those spots that feels like a totally different world compared to the city. Tucked along the Illinois River, it’s known for its canyons, waterfalls, and forested trails that change with the seasons. Riders love it not just for the views, but for the trip getting there. The ride takes you through smaller towns and open stretches of road that are a nice break from Chicago’s constant movement.

As far as Chicago motorcycle routes go, this is one of the best day trips. The ride out is just under two hours, and you’ll hit some nice rural roads if you avoid the highways. Route 71 and Route 6 are both great picks if you want a more scenic ride into the park.

Once you’re there, park the bike and stretch your legs on one of the many hiking trails. You’ll find more than a dozen sandstone canyons to explore, and if it’s spring or summer, chances are you’ll run into a few waterfalls too. There’s also a visitor center with maps and info if you want to make it more of a full-day experience.

Tour 2: Rock River Run

Start: Oregon, IL

Distance from Chicago: 100 miles west

This is one of those routes that riders in northern Illinois keep coming back to. The Rock River Run starts in Oregon, IL and follows the river south to Dixon. It’s only about a 25-mile ride between the two towns, but what makes it worth the trip is how smooth and steady the route feels with plenty of curves, steady two-lane roads, and almost no traffic.

You’ll start near Lowden State Park, where you can stop and check out the 48-foot-tall Black Hawk Statue that overlooks the river. From there, head south on IL-2. The road stays close to the water the whole way, with wide shoulders, clear sightlines, and just enough turns to keep it interesting. You’re not going to hit any tight switchbacks here, but that’s not what this route is about.

The full loop (Chicago to Oregon, down to Dixon, and back) makes for a solid full-day ride without getting too far from home. If you’re planning a motorcycle tour in Chicago and want something that feels smooth, local, and quiet, this route checks a lot of boxes. Among Chicago motorcycle routes, this one offers a steady pace, easy roads, and just enough along the way to make the ride feel worthwhile.

Tour 3: Kankakee River State Park

Start: 5314 W Route 102, Bourbonnais, IL 60914

Distance from Downtown Chicago: 55 miles south

Fees and Permits: Free entry; parking available on-site

If you want to stay closer to the city without sacrificing scenery, Kankakee River State Park is an easy pick. It’s about an hour south of downtown and makes for a quick ride that doesn’t feel rushed. After coming back up from the Rock River Run, this is a good way to keep the day going or plan a separate ride for another weekend.

The best part about this ride is Route 102, which runs along the north side of the Kankakee River. It’s smooth, shaded in parts, and gives you long views of the water without a lot of stops. On the other side, Route 113 takes a different path with more open stretches and fewer curves, so you can pick whichever route fits your riding style. A lot of riders like to do one on the way in and the other on the way out.

Inside the park, there are plenty of places to pull over and walk around if you want to take a break. The trails are short and easy to follow, and there are spots near the water where you can sit for a bit before heading back. It’s not overly crowded either, which makes it feel a little more relaxed than some of the other state parks near the city. This one is easy to plan around, and it’s a practical option if you don’t want to be on the bike all day. Just ride, take in the river, and get a quick reset without having to go far.

Tour 4: Sheridan Road

Start: North Avenue and Lake Shore Drive, Chicago

Distance from Downtown Chicago: 38 miles south

Sheridan Road is one of the few routes that lets you ride straight out of downtown without jumping on the highway. The road takes you north through some of the oldest and most historic neighborhoods in the city, including Uptown and Rogers Park, before crossing into Evanston. Traffic lights are frequent early on, especially through Lakeview and Edgewater, but once you pass Loyola University, things start to open up.

From Evanston to Lake Bluff, the road runs parallel to the lake and passes some well-known landmarks you won’t catch from the expressways: Baha’i House of Worship in Wilmette, Ravinia Park in Highland Park, and Fort Sheridan Forest Preserve just before you reach your endpoint. Most of the road is in good condition, with some minor dips and uneven pavement in Kenilworth and Glencoe. Watch for cyclists in this stretch, especially on weekends.

The entire ride is a slow cruise, so this isn’t a route to take if you’re looking to pick up speed. But if you want something scenic and steady that keeps you close to the shoreline without leaving the suburbs, this is one of the few routes near Chicago that actually delivers. Lake Bluff has a small downtown with parking and a few local spots to grab food before heading back south

Tour 5: Lake Shore Drive (U.S. Route 41)

Start: Hollywood Avenue, Chicago, IL

Distance from Chicago: Starts in the city and runs south for about 16 miles

Lake Shore Drive is one of the most iconic roads in Chicago and gives you a straight shot through the city with Lake Michigan on one side and the skyline on the other. It’s not a long ride, but it’s one of the few places in the city where you can actually enjoy being on a motorcycle without needing to leave town. If you’re starting from Hollywood Avenue on the north end, you’ll ride past landmarks like Navy Pier, Grant Park, and Museum Campus before the road transitions into South Shore Drive.

The road is usually in good condition, but construction pops up often around the Museum Campus or near Oak Street Curve. Speed limits are posted at 40 mph, and police patrol this route regularly, so it's not the place to push the pace. Mornings before 8 a.m. and late evenings tend to be the best windows to ride it without being stuck in traffic.

If you’re riding through the city and need a fast way to move between neighborhoods without hitting dozens of stoplights, this is the road you take. It also connects easily to other outbound routes like Sheridan Road to the north or South Shore Drive into the southeast suburbs, so it works well as part of a longer loop.

Tour 6: Route 66 Starting Point

Start: Adams Street and Michigan Avenue, Chicago, IL

Distance from Chicago: Located in the Loop

Most people pass by the corner of Adams and Michigan without realizing it marks the beginning of one of the most famous highways in the country. There’s no big monument or tourist setup, but that’s part of what makes it feel authentic. The Route 66 sign is posted on a streetlight right near the Art Institute, just across from Millennium Park. It’s a simple sign on a busy street, surrounded by historic buildings and constant movement, just like it was when the road first opened in the 1920s.

Once you leave downtown, the ride follows Ogden Avenue, which cuts through the southwest side of the city and takes you into suburbs like Cicero and Berwyn. This part of the route is still lined with some of the original diners, motels, and vintage signage that give it character. Traffic through here can be unpredictable, especially during mid-morning and early evening, so it helps to plan around the rush.

Riding this stretch is about starting in a spot that’s been part of motorcycle and road trip culture for nearly a century and following a path that still carries a lot of that original energy. Whether you’re using it to launch a longer trip toward central Illinois or just taking it as far as Joliet before turning back, this route gives you a clear connection between the city and the road ahead.

Motorcycle Rentals in Chicago

Looking to ride any of these routes without bringing your own bike? Riders Share has you covered. You’ll find a wide range of motorcycles available for rent in Chicago, including popular brands like Harley-Davidson, BMW, Honda, and Yamaha. Some rentals even come with gear like helmets or jackets, so you don’t have to worry about packing everything. Whether you’re planning a quick ride through the city or heading out for the weekend, Riders Share gives you flexible options from trusted local riders.

Have a Few Motorcycle Rides in Chicago Worth Exploring? Share Them Today!

Know a few routes that deserve more attention? We want to hear about them. Riders Share is built by real riders who’ve experienced these roads firsthand, and your input helps others plan better motorcycle tours in Chicago. Share your go-to spots, favorite detours, or tips for new riders exploring the area for the first time. You can add your ride to our Chicago experiences page and help others discover what makes these roads worth the trip. And if you’re looking for more rides in Chicago, you’re heading in the right direction. Check out the experiences page today!