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Chicago is flat, gridded, and threaded with more than a dozen long trails: a car-free lakefront, two rail lines turned into parks in the sky, forest-preserve routes that leave the city limits without ever crossing traffic, and the suburban path that invented the American rail-trail. Here is the local’s map, with the miles, the trailheads, and how to bring the bike home on the train.
Chicago is the flattest big city in America, which makes it one of the easiest to ride. Start with the three rides you can reach on a Divvy: the lakefront, an elevated rail line, and a riverbank that only recently became passable.
Eighteen and a half car-free miles from Edgewater to South Shore, past four harbors, a dozen beaches and most of the postcard skyline. Since 2018 riders and walkers get separate lanes for nearly the whole run, and the Navy Pier Flyover, finished in 2021, carries the trail over the river without a single crosswalk.
A freight line elevated in the 1910s, reborn in June 2015 as a linear park twenty feet above the street, running through Wicker Park, Bucktown, Humboldt Park and Logan Square with ramps every few blocks. An eastward extension toward the river is in design, with a late 2027 target.
Two miles along the Chicago River linking Clark, California and Horner parks, finished in 2021. The centerpiece Riverview Bridge, opened in 2019, floats the path over the water itself and is the longest river-spanning pedestrian bridge in the city.
The South Side holds the trail named for the fastest man on two wheels, the city’s only true bike park, and the beginnings of a canal-bank route toward Indiana. Next in line: the Englewood Nature Trail, an elevated rail conversion in the works along 59th Street with an opening targeted around 2027.
An old rail spur running from Dan Ryan Woods across the Little Calumet to Whistler Woods, named for Marshall “Major” Taylor, the 1899 world sprint champion and one of the first Black world champions in any sport, who spent his final years in Bronzeville. A restored natural area and new public art joined the trail in 2026.
The city’s purpose-built bike playground inside a wetland park: an asphalt pump track open year-round, beginner-friendly singletrack, and a set of gravity jump lines on the Big Hill opening in summer 2026, with the Ford Calumet Environmental Center at the gate.
A canal-bank route along the Calumet-Sag Channel planned to run 26 miles from Lemont to the Burnham Greenway near the Indiana border. The western half, Lemont to Alsip, has been open since 2015; the eastern half has been filling in section by section.
The north corridors are the region’s oldest habit: leafy, continuous, and pointed at two destinations worth the miles, the Chicago Botanic Garden and the state line.
The classic Saturday ride: out of the city at Gompers Park (the 2016 extension brought the trailhead to Foster and Pulaski), up the river forest to the Chicago Botanic Garden. A short jog on Lake Cook Road connects onward to the Green Bay Trail and the Skokie Valley path.
The trackbed of the North Shore electric line, running beside the Metra tracks through the lakefront suburbs. At its north end the Robert McClory path carries the same corridor through Lake County to the Wisconsin line, where Kenosha County trails take over.
More than 31 unbroken miles of river woods from the Wisconsin line south through Lake County, with further sections continuing into Cook. Crushed gravel, shaded, and about as far from traffic as a ride here gets.
The northwest suburbs’ favorite training loop: a 7.3-mile circuit around the lakes of Ned Brown Preserve with two spurs bringing the paved total to 10.4 miles, plus the fenced elk pasture that has kept a small herd at the preserve’s corner since 1925.
The western suburbs are stitched together by the trail that invented the American rail-trail. In 1963, Naperville naturalist May Theilgaard Watts wrote a letter to the Tribune proposing that the abandoned electric interurban line be saved as a footpath; the result was the first successful rails-to-trails conversion in North America, and the model for every one since.
Sixty-one crushed-limestone miles on the old Chicago, Aurora & Elgin interurban: a main stem from Maywood to Wheaton, branches to Elgin and Aurora, and spurs to Geneva and Batavia. Flat, shaded, and threaded through a dozen downtowns built around the very stations the railroad left behind.
Down the Fox through Elgin, St. Charles, Geneva, Batavia and Aurora, crossing the river on old rail bridges and meeting the Prairie Path in four places. The section north of Elgin belongs to the Grand Illinois Trail, the 500-mile loop that links the region’s trails into one route.
The Fox River Trail’s northern continuation on an old Chicago & North Western line, 26 miles through McHenry County to the state line. Ridden together with the Fox River Trail it makes a fifty-plus-mile day along one river.
A quiet 25-mile creekside route through the near-west preserves, passing Brookfield Zoo country. A connector finished in Villa Park in 2024 tied it into the Prairie Path and the Great Western Trail, so the western network now closes the loop.
A rolling crushed-limestone loop around the entire Argonne National Laboratory campus, with ravines, pine plantations and an actual waterfall at Rocky Glen. The closest thing to a proper gravel ride inside the metro area, and the hilliest ten miles in DuPage County.
The Palos preserves sit on a glacial moraine that rises 150 feet over the surrounding flat, which by local standards is alpine. Below it, two canal corridors head downstate.
The region’s mountain-bike headquarters: more than 27 miles of volunteer-built singletrack across 15,000 acres of woods on Mount Forest Island, maintained by the CAMBr club, from beginner flow to rooty black-diamond lines. Multi-use and shared with hikers and horses, sunrise to sunset.
Twenty-two straight miles through New Lenox, Frankfort, Matteson and Park Forest on a corridor first cleared in the 1800s for a wooden plank wagon road that never got built. The rail line that used it instead is now one of the best-kept paved trails in the region, with downtown Frankfort as the classic midpoint stop.
The towpath of the Illinois & Michigan Canal, the 1848 ditch that connected the Great Lakes to the Mississippi and made Chicago the crossroads of the country. Now 61.5 flat crushed-stone miles past locks, aqueducts and canal towns, the granddaddy of long gravel days out here.
The trick to riding one-way trails is that the trains carry bikes. Metra allows bikes, e-bikes included, on all trains at all hours, a policy in place since January 2024; you lift the bike aboard yourself and park it in the marked cars. CTA trains take bikes every hour outside the weekday rushes (7 to 9 in the morning, 4 to 6 in the evening), two per car by the green decal. Every CTA and Pace bus carries a fold-down rack on the nose. And Divvy, the bike-share system, now runs more than 1,100 stations across Chicago and Evanston, the largest bike-share service area in North America, with e-bikes that can lock to ordinary racks.
The network on the street is growing too: the city marked 100 miles of new bikeways completed in the two years to fall 2025, the 606 is designing its extension east toward the river for late 2027, and the elevated Englewood Nature Trail is in the works on the South Side. The ride keeps getting longer.
Trail access has quietly become one of the most-requested lines on a buyer’s wish list, and we tour the blocks along the 606, the Lakefront Trail and the North Branch constantly. If starting a ride from your own front door is part of the brief, tell us which trail; our neighborhood guides and parks guide cover the green space around every one of them.
Talk to The Boulevard Group