Chicago is the largest city in Illinois and the third-largest in the United States, set on the southwest shore of Lake Michigan. It is known for its pioneering skyscraper architecture, deep-dish pizza, world-class museums, live blues and jazz, and a 26-mile lakefront of parks and beaches. Visitors can move between a dense downtown, the Chicago River and more than 70 distinct neighborhoods on the CTA 'L' train.
Top trails
Routes worth lacing up your boots for.
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1
Chicago Lakefront Trail
An 18-mile paved, car-free path hugging Lake Michigan from Ardmore Avenue on the north side to 71st Street on the south side. It passes Lincoln Park, North Avenue Beach, Navy Pier, Museum Campus and Promontory Point with constant skyline views.
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2
The 606 (Bloomingdale Trail)
A 2.7-mile elevated former railway line converted into a park, running between Ashland Avenue and Ridgeway Avenue through Wicker Park, Bucktown, Humboldt Park and Logan Square. Twelve access points roughly every quarter-mile are all accessible to people with disabilities.
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3
Chicago Riverwalk
A 1.25-mile pedestrian promenade along the Chicago River with six themed 'rooms' between Lake Michigan and Lake Street, passing under the historic bridges with cafes, public art and constant views of the surrounding skyscrapers.
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4
Promontory Point Lakefront Loop
A landscaped peninsula designed by Alfred Caldwell with limestone council rings, a limestone revetment and a meadow, linked to the Lakefront Trail. It offers one of the best southern views of the city skyline across the lake.
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5
Montrose Point Bird Sanctuary (Magic Hedge)
A migratory bird sanctuary with a thicket known as the Magic Hedge that draws many species during spring and autumn migration. Short footpaths join the Lakefront Trail and Montrose Harbor, with a skyline view from the point.
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6
Lincoln Park Nature Boardwalk
A quarter-mile boardwalk around the South Pond in Lincoln Park with native plantings, turtles, herons and a pavilion framing the downtown skyline. It joins the Lincoln Park Zoo grounds and the Lakefront Trail.
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7
North Branch Trail (Forest Preserves of Cook County)
A paved and crushed-limestone trail through the Forest Preserves of Cook County along the North Branch of the Chicago River, running north from Caldwell Woods toward the Chicago Botanic Garden in Glencoe through woods, meadow and river floodplain.
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8
Skokie Lagoons Trail
A chain of lagoons and surrounding woodland in the Forest Preserves of Cook County, with flat trail along the water. It is good for birds, turtles, herons and quiet cycling just north of the city.
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9
Indiana Dunes: West Beach Dune Succession Trail
A one-mile loop with wooden steps climbing through dune stages from beach grass to oak forest, with views over Lake Michigan and, on clear days, the Chicago skyline across the water.
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10
Indiana Dunes: Mount Baldy and Beach Walk
A shifting dune climbed by a short trail and wooden steps, with a long beach below. Mount Baldy is among the tallest and most-visited dunes in the park and offers lake views from the crest.
Trail difficulty levels
Pick a route that matches your fitness and experience.
Mostly flat, well-marked paths. Suitable for families and casual walkers.
Some elevation gain, longer distances. Requires basic fitness.
Significant climbs and exposure. Requires good fitness and route-finding.
Technical terrain, scrambling, or alpine conditions. Experience essential.
Local hazards
What to watch out for on the trail.
Sudden weather changes — always carry rain gear and warm layers.
Wildlife encounters — make noise on the trail and store food properly.
Trail conditions can deteriorate after rain — check recent reports before setting out.