55
Calumet Beach, Sag Valley Forest Preserve & Salt Creek loop from Chicago
109.7 km216 m
Cycling routes / United States / Chicago
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.
Cal-Sag Trail and Centennial Trail
96.3 km147 mChicago
67.0 km94 mErie Lackawanna and Pennsy Greenway Loop
41.9 km76 mGrand Illinois Trail: Chicago Lakefront to Wolf Lake
75.4 km142 mLakefront Trail
30.4 km44 mNorth Branch Trail Loop
50.1 km85 mThorn Creek Trail
43.8 km81 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
Ride Chicago at the right time
Compare routes in Chicago, choose a departure window that matches the forecast, and navigate with confidence. With Tailwind GPS you get route planning, wind-aware scoring, and turn-by-turn guidance in one place — built to help cyclists find their best ever ride.