This 18-mile (29-km) stretch is hard to beat when it comes to cycling in Chicago. Hugging the shore of Lake Michigan all the way from Hyde Park‘s museums to Edgewater’s beaches, the trail passes many of Chicago’s most popular attractions and provides amazing views of that awesome skyline. Be sure to stop off at the ever-popular free Lincoln Park Zoo or at Museum Campus to make a day of it. There are also restrooms and water fountains at regular intervals.
Should you feel like carrying on when you reach the end of the Lakefront Trail, North Sheridan Road stays close to the lake for another 18 miles or so and is totally worth following. Rogers Park’s Loyola University and Evanston’s Northwestern offer picturesque campuses and museums, but the real gem on this trail is the stunning Bahá’í House of Worship in Wilmette. Stop there to gaze at the incredible temple that took 50 years to build before carrying on to the Chicago Botanic Garden in Glencoe, where you can grab a train back to the city.
Another great Chicago trail also leads to the Chicago Botanic Garden. The North Branch Trail is a paved 20-mile (32-km) route that follows the North Branch of the Chicago River, hence the name. Beginning at the forest preserves in Forest Glen, the trail winds through woods and leafy suburbs, passing golf courses and the Skokie Lagoons before reaching the garden. Parking options along the trail and amenities are provided.
Heading southwest of the city, the full length of the Cal-Sag Trail is still being constructed, but a 13-mile (21-km) section opened in 2015. The completed tree-lined stretch travels along the Cal-Sag Channel, from Sagawua Canyon through the Sag Quarries Nature Preserve to Alsip’s Freedom Park. The trail will eventually be 26 miles long and end in Calumet City on the border with Indiana.
Back in the city, this 2.7-mile (4.4-km) park trail along Bloomingdale Avenue was converted from an old elevated train track, as Chicago’s answer to New York’s the High Line. It was completed in 2015 and runs from Bucktown to Logan Square, with lots to see and do on the way. Although short in comparison to other trails, a chance to see the city from a different perspective makes this path worth several laps.
West of the city, the Salt Creek Greenway Trail travels a lengthy 26.7 miles (43 km) from the Brookfield Zoo to Busse Woods Forest Preserve. Not all of the trail is paved, and a few short sections require cycling on the road, but the majority passes through beautiful forest preserves and mostly quiet suburbs.
Intersecting the Salt Creek Trail is the Illinois Prairie Path, one of the country’s first rail-to-trail conversions. Following the path of the Chicago, Aurora and Elgin electric railroad, this trail combines five segments and the three main branches meet in Wheaton’s Volunteer Park. The whole path is a hefty 61 miles (98 km) long.