Chicago is known for being one of the best cycling cities in the US - in fact, in 2021 it ranked 30th out of 200 cities according to a study that rated cities on their access to cycling, climate, community, and safety.
Along with flat terrains and over 250 miles of bike lanes (18.5 miles of which have barriers, and 67 miles of which have buffers), Chicago also puts a lot of funding into cycling.
In 2018, the city spent $53.5 million on bike-related infrastructure, and the Divvy bike sharing system - owned by the Chicago Department of Transportation - operates almost 6,000 bicycles that cover nearly the entire city.
If you’re considering cruising the Windy City by bike, here are some of the best trails in and around Chicago.
Deer Grove is Cook County’s oldest preserve, and offers cyclists, pedestrians, hikers, and even cross-country skiers the opportunity to connect with the natural world through a vast array of forests, wetlands, ravines, savannas and prairies. During the cooler months, you can expect crisp air, smaller crowds, and the spectacular scenery of changing foliage - you may even see some of the wildlife, particularly the deer that the preserve is famous for.
The preserve’s habitats are accessible through two expansive looping trails: Paved and unpaved. The primary paved path is 4 miles, with an additional 2.8-mile loop that connects to a 1.2-mile segment on the western side. The unpaved trail is 10 miles, with additional unpaved trails of 5.4 and 2.6 miles.
If you want to extend your ride even further, the Deer Grove Trail connects with the northern section of the Palatine Trail, giving you an additional 8.5 miles of trail to explore.
There are some “bike prohibited” unpaved trails so make sure you look out for the signage. Even though they may look irresistible, these areas are often patrolled and you could end up with a $75 fine - but there are still plenty of unpaved bike-friendly trails! Take note that some of the unpaved paths and ravines are quite advanced, and should only be attempted by experienced cyclists with mountain bikes.
The trail system at Deer Grove Preserve is perfect for a day of adventuring, or, if you want to get away from it all for a bit longer, there’s also a recently renovated campground that offers restrooms, water, and a convenience store. Cyclists can access the Deer Grove Trail through the East or West parking lots.
Just a short drive outside of Chicago, the Des Plaines River Trail is a lush oasis, perfect for anyone hoping to escape the hustle and bustle of the city.
Protecting over 70% of the river in Lake County, the Des Plaines River Trail and Greenway’s gravel trail goes through almost the whole length of Lake Country for 31.4 miles, giving cyclists an incredible expanse to enjoy the wildlife habitat of the area, including deer, birds, snakes, and turtles.
The trail begins at Russell Road in Wadsworth south, then continues through Lake Cook Road, and connects to the Cook County Forest Preserve trails. If you cycle from the Des Plaines River Trail into Cook County Forest Preserve, you can extend your exploration to just over 56 miles.
The trail surfaces range from pavement to crushed stone to single-track forest trails, and the terrain changes quickly - so make sure you’re aware of where you’re going. Novice cyclists will enjoy the north to south trail where, for the first 20 miles, the trail is traveled and well-maintained.
For those wanting a bit more of an adventure, continuing further south will take you into narrower corridors that are less traveled and filled with roots in many segments. At times, this trail intersects with busy routes, so keep an eye out for pedestrians, other cyclists, and motorists. These crossings are well marked and give cyclists the right of way over cars, but it’s always good to be cautious.
Parking lots are dotted along the whole length of the trail, so it’s easy to access at a number of points, and amenities throughout the preserve include restrooms, picnic areas, and water fountains.
The Ned Brown Forest Preserve (also known as Busse Woods) is a property of over 3,500 acres in the northwest of Chicago. The cycling trail takes you into a wooded area with incredible scenery of ponds and lakes, and even a few elk pastures.
Because the trail goes through a dense forest, it’s ideal for a fall or spring ride where you can watch the leaves change color. One of the main benefits of this trail is that very little of it goes along roads, keeping you safely away from motorists. While it’s a popular destination on warm weekends, you’ll have the trails almost to yourself in the cooler months when there are far fewer visitors.
The main loop, The Busse Woods Trail, which circles the lakes and meadows, is just under 8 miles long but you can extend the trail to 11 miles if you explore the shorter side loops too. The trails are mostly paved and are suited for all skill levels.
If you want to extend your ride even further, on the west the trail connects with the Schaumburg Bikeway - a 3.5-mile ride that connects you to Town Square, the Sculpture Garden, and Lancer Creek Bike Path.
The Ned Brown Forest Preserve trails are open from sunrise to sunset, and you can enter the park from E. Higgins Road and Arlington Heights Road in Elk Grove Village.
Located less than half an hour outside Chicago, the Green Bay Trail is a moderate out and back 17.5-mile trail. While out and back trails often aren’t as exciting as loop trails because you double back on the same scenery, the Green Bay Trail is worth seeing twice!
The trail goes through North Shore towns and mostly stays within a mile of Lake Michigan, giving you the option to take your choice of on-road side trips for beautiful views of the lakefront. The trail itself is primarily asphalt and some limestone - take note that the limestone can get messy and gummy up your gears after rain.
The trail is suitable for most cyclists, but inexperienced cyclists or those riding with children should take care when it comes to road crossings or road riding (which there is a small portion of in a residential area).
No list of Chicago bike trails would be complete without mentioning the Lakefront Bike Trail. Made up of 18.5 miles of shared-use paved paths, the Lakefront Trail is one of the most scenic bike paths in the city, and also one of the most popular.
But it’s not just the trail itself that’s an attraction - it takes you through countless Chicago beaches and parks, with endless waterfront dining options and attractions like the Lincoln Park Zoo, Museum of Science and Industry, and Adler Planetarium.
If you arrive in Chicago without your bicycle, Divvy has a station at the Lakefront Trail where you can rent a bicycle for 30 minutes for $3.30. If you want to keep the bike for longer, it’s an extra $0.15/minute.
Unsurprisingly, the Divvy station at the Lakefront Trail is their busiest and they regularly run out of bicycles in the warmer months. Luckily, going in the off-season means there are fewer people out and about - so you’re much more likely to get a bike without needing to wait.
This one isn’t a trail, but an event that takes place annually just before the start of fall. The next one is on 18 September 2022. Known as “the last ride of summer” and organized by the Evanston Bike Club, this event has hundreds of participants who enjoy scenic biking.
Beginning in Chicago and ending in Wisconsin, the Classic Century takes you 100 miles through residential neighborhoods, architectural sites, and down Lake Michigan bike paths. Due to the length of the ride, Evanston Bike Club notes that this is best for “confident and conditioned” cyclists. But if you’re not quite up for 100 miles, there are other options too.
There are also 62-mile, 50-mile, and 25-mile routes to choose from, with the latter the perfect distance for rides with the whole family.
Whichever route you choose, if you’re covered with Sundays Insurance and have selected racing coverage as an optional add-on, your bike will be covered for any damage you sustain during the event.
On the 100-mile route, there are six rest stops, each supported by local bike shops that offer restrooms, refreshments, and an array of food vendors (one of the main attractions of the ride!) offering everything from pizzas, grilled meat, ice cream, and even pickle juice to replace the sodium from sweating.
Here are some tips for getting the best out of your Chicago cycling experience:
Subscribe to our newsletter for coverage tips, community stories, and enriching cycling experiences delivered straight to your inbox.
