The best cycling routes around Chicago

The Lakefront Trail offers a quintessential Chicago touring cycling experience, tracing the city's iconic shoreline. You'll glide past sandy stretches like Fullerton Beach and the vibrant activity around Belmont Harbor, all while enjoying expansive views of Lake Michigan. This route is a fantastic way to soak in the urban landscape and natural beauty, making it a favorite among locals and visitors alike.

This moderate ride covers 26.3 miles (42.3 km) with a minimal 221 feet (67 metres) of elevation gain, typically taking around 2 hours and 23 minutes to complete. It's an accessible path suitable for most cyclists, whether you're looking for a relaxed spin or a longer workout. Starting early on pleasant days is advisable to enjoy the path with fewer crowds.

Beyond the natural beauty of the lake, the trail connects you to several key Chicago landmarks, including the bustling Navy Pier and the impressive Field Museum. It's a prime example of how the city integrates recreation with its cultural and architectural heritage, offering a unique perspective on Chicago's vibrant character.

Embark on a delightful urban cycling adventure with the Chicago Lakefront and Route 66 Loop, a route that perfectly captures the essence of the Windy City. You'll glide along the iconic Chicago Lakefront Trail, where the city's impressive skyline meets the vast expanse of Lake Michigan, offering spectacular views, particularly near the Shedd Aquarium. The journey also takes you past the historic Field Museum and the symbolic start of Route 66, blending natural beauty with cultural landmarks on a smooth, paved path.

This easy touring cycling route is incredibly accessible, covering 15.6 miles (25.1 km) with a gentle 142 feet (43 metres) of elevation gain, making it suitable for all skill levels and taking approximately 1 hour and 26 minutes. For convenient access, consider using Chicago's extensive public transport network, as many lines serve the downtown area. While specific parking isn't detailed, numerous garages are available, and cycling in the late morning on a weekday can help you avoid the busiest times on the popular Lakefront Trail.

What makes this route stand out is its unique combination of Chicago's vibrant urban core and a touch of American road trip history. It's a fantastic way to experience the city's energy, see major attractions, and even touch upon the legendary Route 66, all within a manageable and enjoyable cycling loop. This trail is a prime example of the best cycling routes Chicago Lakefront and Route 66 has to offer for a relaxed sightseeing tour.

Imagine cruising along the edge of Lake Michigan with the Chicago skyline as your constant companion. The Chicago Lakefront Trail offers an easy touring cycling experience, stretching for 11.4 miles (18.3 km) with a negligible 82 feet (25 metres) of elevation gain. You'll pass by popular spots like Fullerton Beach and Ohio Street Beach, enjoying uninterrupted lake views and a refreshing breeze. It's a fantastic way to see the city's iconic waterfront without any strenuous effort, taking just over an hour to complete.

Planning your ride is straightforward, but consider an early start, especially on warmer days or weekends, to beat the crowds. The trail is well-connected to Chicago's public transport network, making access simple from various neighborhoods. While parking is available near the lakefront, spots can fill up quickly during peak hours. Spring and autumn provide comfortable cycling weather, though summer mornings are also pleasant before the midday heat.

This route is a quintessential Chicago experience, showcasing the city's unique blend of urban architecture and natural beauty along the vast expanse of Lake Michigan. It's a family-friendly option and a favorite among locals and visitors alike for a relaxed outdoor activity. The paved path ensures a smooth journey, making it suitable for all skill levels and a great introduction to cycling in the city.

The North Branch Trail and Botanic Garden Loop offers a substantial touring cycling experience, primarily on paved surfaces that wind through the natural areas of the North Branch Trail system. You'll enjoy long stretches of dedicated cycle way, including sections of the North Branch Red Paved Trail and North Branch Black Paved Trail, leading to the picturesque Chicago Botanic Gardens. This route is designed for cyclists who appreciate extended rides and the blend of natural scenery with a cultivated destination.

Planning for this difficult 57.9-mile (93.3 km) ride, which typically takes 5 hours and 21 minutes, requires an early start to make the most of your day. While specific parking is not detailed, you can look for access points near Northcroft Park or other trailheads along the North Branch Trail. Remember to pack enough water and nutrition for the duration, as this is a significant undertaking.

This loop stands out as one of the best cycling trails near Chicago Botanic Garden, offering a unique opportunity to combine a challenging workout with a visit to a renowned natural attraction. It's an excellent choice for experienced cyclists looking for popular routes cycling that provide both distance and a rewarding destination, distinguishing it from shorter, more beginner-friendly options in the area.