A Guide to Cycling Chicago: The Coolest Rides and More

Whether exploring any city for the first or hundredth time, cycling offers a unique perspective, granting riders a fresh view of their surroundings. In Chicago, where transportation options abound, cycling stands out for its convenience, enjoyment, and efficiency blend. Renowned as one of the nation’s premier cycling cities, Chicago owes its status to a combination of environmental factors, cultural appreciation, and significant infrastructure investments.

The city’s affinity for cycling traces back to the late nineteenth century when the first bicycles, “boneshakers,” appeared on its streets in the 1860s. In the 1990s, Mayor Richard M. Daley, a passionate cyclist, propelled Chicago’s reputation as a bike-friendly metropolis. Over the ensuing decade, the city saw the creation or enhancement of over a hundred miles of bikeways and the installation of nearly eight thousand bicycle racks, marking a significant stride in promoting cycling as a viable mode of transportation.

When to Cycle in Chicago:

Chicago has a continental climate marked by cold winters, hot summers, and frequent fluctuations in temperature, humidity, cloud cover, and wind direction. Spring and fall are often seen as the most enjoyable seasons due to their moderate temperatures. Lake Michigan is vital in moderating Chicago’s climate while contributing to increased winter snowfall. The city’s nickname, the “Windy City,” is partly due to the invigorating lake breeze.

Spring, though fleeting, offers many attractions in Chicago, with over 500 parks bursting into bloom. Notably, Lincoln Park ranks as the third most visited park in the United States, trailing Central Park in New York and the National Mall in Washington DC.

Summer in Chicago brings warm and humid conditions, with July recording average highs of 27 degrees Celsius, making it the warmest month of the year. 

September is an ideal time to visit Chicago. It is characterized by warm and relatively dry weather, with daily highs averaging around 23 degrees Celsius.

Winter in Chicago can be severe, with temperatures remaining below freezing for months and the possibility of heavy snowfall and blizzards.

Top Chicago cycling routes

Lakefront Trail to Indiana 

Distance: 82.5 km with 33 m elevation gain

The Chicago Lakefront Trail follows the shoreline of Lake Michigan, linking multiple beaches, recreational facilities, museums, and cultural attractions. This scenic route leads to Wolf Lake, an expansive 804-acre lake that straddles the Indiana and Illinois state line near Lake Michigan.

Chicago by Bike Biking from Chicago into Indiana [4K]

Along the coast to Highland Park

Distance: 76.9 with 164 m elevation gain

Highland Park, nestled in the heart of the North Shore, beckons cyclists with its blend of urban sophistication and natural beauty. Begin your journey in the pedestrian-friendly Central Business District. As you pedal away from the city center, you’ll soon find yourself enveloped in the serenity of tree-lined streets and expansive lakefront trails.

The Ravinia District provides a charming backdrop for your ride. Take a moment to appreciate the tranquil natural beauty surrounding you, from lush green parks to breathtaking waterfront views.

Chicago – LaBagh Woods

Distance: 41.3 rm with 18 m elevation gain

LaBagh Woods, situated at the southern entrance of the renowned North Branch Trail, is a haven for nature enthusiasts seeking diverse landscapes and outdoor activities. This picturesque site boasts wooded areas, wetlands, savannas, and sedge meadows, providing a rich tapestry of habitats to explore.

The trail itself, though predominantly flat, is suitable for a variety of activities, including walking, hiking, biking, and trail running. A highlight of the area is the 4-mile paved loop trail encircling Skokie Lagoons, which serves as a picturesque link between the North Branch Trail and the esteemed Chicago Botanic Garden. 

Chicago – North Shore Channel Trail & Skokie Lagoons

Distance: 67.7 km with 80 m elevation gain

The North Shore Channel Trail offers a picturesque route from northern Evanston to Chicago, showcasing the area’s natural beauty and recreational opportunities. On the west side, cyclists can traverse a smooth paved trail that meanders through several parks, providing a scenic and enjoyable journey for riders of all levels.

At the heart of this trail lies the expansive Skokie Lagoons, spanning 894 acres and offering many outdoor activities for visitors to enjoy. For cyclists seeking a more structured ride, a 1.6-mile asphalt bike path runs along the western edge of the lagoons between Willow Road and Tower Road. Additionally, a 4.2-mile loop encircles the lagoons, stretching from Tower Road to Dundee Road and extending the North Branch Bicycle Trail to the renowned Chicago Botanic Gardens.

Virtual Cycling 45-Minute Bike Ride Around Skokie Lagoons and Across Chicago Botanic Garden

Calumet Beach, Sag Valley Forest Preserve & Salt Creek loop from Chicago

Distance: 111km with 155 m elevation gain

Situated near the Indiana border, Calumet Beach is one of Chicago’s lesser-known gems, boasting tranquility amidst its pristine shores. 

Adjacent to Calumet Beach lies the Calumet Trail, which traces a path along flat terrain beside the South Shore Line’s railroad tracks to the south and the majestic Indiana Dunes National Park to the north. This leisurely trail offers a relaxing journey with minimal road crossings, and thanks to the park’s proximity, it provides ample opportunities to observe the area’s wildlife.

Great Bike Rides of SoCal Salt Creek Trail

Bike-friendly hotels in Chicago  

Hampton Inn Chicago North-Loyola Station: 1209 W Albion Ave, Chicago, IL 60626, United States link | instagram 

Omni Chicago Hotel: 676 North Michigan Avenue, Chicago, Illinois, 60611 link | instagram

Where to eat

Heritage bikes and coffee: Lakeview, Chicago, IL 60657, US link | instagram

А bicycle shop and a cafe. It also offers bicycle repairs and maintenance services.

Cafe Mustache: 2313 N Milwaukee Ave, Chicago, IL 60647, United States link | instagram

Bike rentals

3rd Coast Cycles: 115 N Lakeshore Dr Chicago, IL 60601 link | instagram

Wicker Bicycle Rentals: 1205 N Milwaukee Ave 1st floor, Chicago, IL 60642, US link

Bobby’s Bike Hike: 540 N Lake Shore Drive, Chicago, IL 60611, US link | instagram

If you know of any cool routes around Chicago or nearby suburbs, we’d love it if you could share them with our WhatsApp community. Your input means a ton to us and really makes our materials better. Thank you for your continued support and collaboration!

Read more about cycling in the US: 

Сycling Boulder: The Colorado Hidden Cycling Mecca

Cycling San Francisco: The Essentials

A Cyclist’s Guide to Santa Monica, California

12 of the World’s Most Spectacular Long-Distance Cycling Routes

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