Bicycling in Chicago offers some of the most scenic and diverse riding in the Midwest, and the Best Western Plus Hillside puts you right in the center of it all. From the iconic Lakefront Trail to the forest‑lined paths of Busse Woods and the North Branch Trail leading to the Chicago Botanic Garden, cyclists can easily explore every major route from our convenient location with free parking. Whether you’re visiting for leisure, training, or a weekend adventure, this guide highlights the best bike trails Chicago has to offer.
Bicycling in Chicago: The Ultimate Guide to the City’s Best Bike Trails
Chicago is one of the most bike‑friendly cities in the Midwest, offering riders everything from scenic lakefront views to forest‑preserve loops and botanical‑garden pathways. Whether you’re a casual cyclist or a seasoned rider, the region’s interconnected trail system makes exploring Chicagoland on two wheels both easy and unforgettable. If you’re searching for the best places to bike in Chicago, these top routes deliver the perfect mix of nature, skyline views, and smooth, well‑maintained paths.
Chicago Lakefront Trail – 18.5 Miles of Iconic Waterfront Riding
The Chicago Lakefront Trail is the city’s most famous bike route, stretching 18.5 miles from Jackson Park on the South Side all the way past downtown Chicago, Navy Pier, and up through Lincoln Park, ending near Hollywood Avenue. Riders enjoy uninterrupted views of Lake Michigan, beaches, marinas, and some of Chicago’s most iconic landmarks. A highlight for many cyclists is the stretch past Lincoln Park Zoo, where lush parkland and skyline views create one of the most photogenic rides in the city.
This trail is ideal for long, scenic rides and is perfect for visitors who want to experience Chicago’s beauty up close.
Forest Preserves of Cook County – Over 300 Miles of Connected Trails
For riders craving a more wooded, nature‑immersive experience, the Forest Preserves of Cook County offer an extensive network of paved and crushed‑limestone paths. One of the most popular is the Busse Woods Trail, an 8‑mile loop located in the Ned Brown Preserve. This trail is known for its wide paths, elk pasture, and peaceful lakeside stretches—perfect for both recreational riders and fitness cyclists.
Another standout route is the North Branch Trail, which connects to the bicycle path running from Devon Avenue through the Chicago Botanic Garden. This ride covers roughly 20 miles from start to finish, guiding cyclists through forest preserves, quiet neighborhoods, and finally into the stunning grounds of the Chicago Botanic Garden in Glencoe. It’s one of the most scenic long‑distance rides in the region.
Your Ideal Bicycling Hotel Near the Illinois Prairie Path
The Best Western Plus Hillside is one of Chicagoland’s most convenient and cyclist‑friendly hotels, perfectly positioned for riders who want fast access to the region’s top trails. Located just minutes from the Illinois Prairie Path, one of the Midwest’s most historic and scenic rail‑to‑trail routes, our hotel gives cyclists a comfortable and reliable home base for exploring more than 60 miles of connected suburban pathways. Whether you’re planning a short morning ride or a full‑day cycling adventure, staying near the Prairie Path makes your trip smoother, safer, and far more enjoyable.
Close to Every Major Chicago Bike Trail — With Free Parking
What makes the Best Western Plus Hillside especially appealing for cyclists is our unbeatable central location. We’re positioned between all the major biking destinations mentioned above — the Chicago Lakefront Trail, the Busse Woods 8‑mile loop, the Forest Preserves of Cook County trail system, and the Devon Avenue–to–Chicago Botanic Garden bicycle path. Riders can easily reach downtown Chicago, the North Shore, or the western suburbs, all while enjoying the convenience of free parking, secure accommodations, and quick highway access.
If you’re planning a Chicago cycling getaway, a weekend ride, or a multi‑trail adventure, the Best Western Plus Hillside offers comfort, convenience, and the perfect starting point for every route. Check our current rates and availability to plan your stay and make the most of Chicago’s incredible biking network.
Frequently Asked Questions About Bicycling in Chicago
What is the best bike trail in Chicago?
The Chicago Lakefront Trail is the most popular route, offering 18.5 miles of shoreline riding.
Is the Chicago Lakefront Trail good for beginners?
Yes. The trail is paved, flat, and well‑marked, making it ideal for new riders.
Where can I bike near nature in Chicago?
Busse Woods and the Forest Preserves of Cook County offer wooded, wildlife‑rich trails, including an 8‑mile loop perfect for peaceful rides.
How long is the bike path from Devon Avenue to the Chicago Botanic Garden?
The North Branch Trail system covers roughly 20 miles from Chicago up to the Botanic Garden in Glencoe.
Where should cyclists stay when visiting Chicago?
The Best Western Plus Hillside is centrally located near all major trails, offers free parking, and provides easy access to the Illinois Prairie Path.