Chicago's Most Scenic Bike Trails

The full 18-mile trail is a gem, but the crush of humanity on the path’s northern sections can trigger bike rage you seriously don’t need. South of Museum Campus, though, things open up all the way to Hyde Park and beyond. Don’t miss the absolute best skyline view from Promontory Point.

This nine-mile path takes you through some of the toniest zip codes on the North Shore. Stop to shop in downtown Winnetka, Lake Bluff or Highland Park, then zag over to the lake for a beach picnic.  

On this jaunt toward the northern ’burbs, you’ll hug the north branch of the Chicago River, beginning on the Northwest Side near Devon and Milwaukee avenues and winding up through the Skokie Lagoons and Erikson Woods on your way to the Chicago Botanic Garden in Glencoe.

Road trip! Most Chicagoans spend at least part of their summers in southwest Michigan anyway, so why not do it on two wheels with a 34-mile ride through small towns, orchards and farms between Kalamazoo and South Haven?

Pack a big lunch if you’re planning to cover the entire length of this 61-mile rails-to-trails path, which stretches across portions of Cook, Kane and DuPage counties and rolls through open meadows, dense forests and several western suburban communities.

Break out the fat tires and head southwest to enjoy more than 50 miles of rugged trails, including the only legitimate mountain-biking routes in the metropolitan area.

Head to the western suburbs with or without your own bike to cruise among towering oaks, maples and ash. Rentals are available, and the paths are car-free all summer long on Fridays from 5:30 p.m. until sunset and on Saturdays and Sundays from 7 a.m. to 9 a.m. (admission charge applies).

Get out of town on 31 miles of crushed gravel that will lead you through the ecosystems (think wilderness and wetlands) of several forest preserves on your way from Chicago all the way up to Wisconsin, if you’re feeling ambitious.

Opening June 6, the Bloomingdale Trail will be the bicycle/pedestrian equivalent of the “L,” a nearly three-mile conduit of recreational access and parkland built on a long abandoned railway that stretches out above the urban fray of Bucktown, Wicker Park, Logan Square and Humboldt Park.