56
Cal-Sag and Centennial trail loop
96.3 km147 m
Best road cycling routes in Chicago today
Here are the best routes to ride in Chicago, ranked using wind, weather, tailwind, and headwind forecasts at 25 km/h.
Departure times are local to Chicago.
- 56
Calumet Beach preserve loop
109.7 km216 m - 56
Chicago Chicago
41.2 km42 m - 56
Chicago Lakefront loop
75.4 km142 m - 56
Chicago loop
67.0 km94 m - 56
Chicago route 7
76.5 km149 m - 56
Erie Lackawanna Pennsy greenway loop
41.9 km76 m - 56
Lakefront trail loop
30.4 km44 m - 56
North Branch forest loop
50.1 km85 m - 56
Thorn Creek trail loop
43.8 km81 m Build your own route
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How routes are ranked
Tailwind scores each route hour by hour using wind, rain and temperature along the ride at a 25 km/h cycling pace. Routes are sorted by weather score for your chosen departure time, highest first.
10 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 routes in the route planner, and follow turn-by-turn guidance when it is time to ride.
Find your best ever ride.
Open the map to score these routes for wind, rain and temperature, then pick the best hour to ride.
Free forever on 3 routes
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Free forever on 3 routes. No card.