Chicago Lakefront loop
75.4 km142 m
Cycling routes / United States / Chicago
Best road cycling routes in Chicago
Here are curated road cycling routes in Chicago. Filter by distance and elevation to find your next ride.
Departure times are local to Chicago.
Chicago loop
67.0 km94 mNorth Branch forest loop
50.1 km85 mThorn Creek trail loop
43.8 km81 mErie Lackawanna Pennsy greenway loop
41.9 km76 mLakefront trail loop
30.4 km44 mCalumet Beach preserve loop
109.7 km216 mCal-Sag and Centennial trail loop
96.3 km147 mBuild your own route
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How routes are ranked
Tailwind scores each route hour by hour using wind direction, weather, and a 25 km/h cycling pace. Routes are sorted by forecast score for your chosen departure time, highest first.
8 curated routes in Chicago, United States.
Nearby places
Plan and navigate rides in Chicago
Compare the best road cycling routes in Chicago, pick a departure time that fits the forecast, and open any ride on the map. Tailwind GPS is a free planning and navigation tool for cyclists: score routes hour by hour, download GPX files for Garmin, Wahoo, or any GPS device, build new loops in the route planner, and follow turn-by-turn guidance when it is time to ride.