The best road cycling routes around Chicago
4.6
(263)
8,466
riders
143
rides
Last updated: November 12, 2025
4.8
(44)
662
riders
1. Grant Park & Lake Michigan shore from Thorndale
30.4km
01:16
40m
40m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.4
(5)
376
riders
2. Lakefront Trail to Indiana — Chicago
75.4km
03:11
140m
140m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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234
riders
3. Chicago – along the coast to Highland Park
76.5km
03:06
150m
150m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
105
riders
4. Chicago – North Shore Channel Trail & Skokie Lagoons
67.0km
02:42
90m
90m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
16
riders
5. Chicago – LaBagh Woods
41.2km
01:39
40m
40m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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