Top Trails and Hikes in Chicago

🥾 Trails and Hikes in Chicago

• Lakefront Trail — The Chicago Lakefront Trail is an 18-mile paved path along Lake Michigan from Hollywood Avenue to 71st Street, passing beaches, parks, museums, and the skyline, one of the best urban bike trails in the US.
• Chicago Riverwalk — Walk the 1.25-mile Chicago Riverwalk along the south bank of the Chicago River from Lake Shore Drive to Lake Street, passing cafes, bars, public art, and boat launches with views of the skyline.
• Lincoln Park loop — Walk the loop through Lincoln Park, Chicago's largest park at 1,200 acres, with the zoo, conservatory, Nature Boardwalk, and North Pond, along the lakefront from North Avenue to Diversey.
• Burnham Harbor walk — Walk around Burnham Harbor near Soldier Field, with views of the harbor, Museum Campus, and the skyline, a pleasant waterfront loop popular with joggers.
• Museum Campus stroll — Walk the Museum Campus, a 57-acre lakefront park connecting the Field Museum, Shedd Aquarium, and Adler Planetarium, with views of the lake and the Chicago skyline.
• North Avenue Beach — Walk or bike along North Avenue Beach, one of Chicago's most popular beaches, with a beach house, volleyball courts, and views of the skyline and Navy Pier.
• Jackson Park trail — Walk the trails of Jackson Park, a 500-acre park on the South Side designed by Frederick Law Olmsted for the 1893 World's Columbian Exposition, with the Garden of the Phoenix and Wooded Island.
• Northerly Island loop — Walk the loop around Northerly Island, a 91-acre peninsula that was Chicago's first airport, now a nature preserve with prairie, trails, and views of the skyline and Lake Michigan.
• Bloomingdale Trail — The Bloomingdale Trail (The 606) is a 2.7-mile elevated rail-trail through Logan Square, Humboldt Park, Wicker Park, and Bucktown, with access parks, public art, and community gardens, Chicago's version of the High Line.
• Montrose Point Bird Sanctuary — Walk the Montrose Point Bird Sanctuary, a 13-acre nature preserve on the lakefront that is one of the best birdwatching spots in the Midwest, with over 300 species recorded during migration.
• Grant Park circuit — Walk through Grant Park, Chicago's 319-acre "front yard" between Michigan Avenue and the lake, with Buckingham Fountain, Millennium Park, the Art Institute, and Grant Park Symphony concerts.
• Promontory Point — Walk to Promontory Point in Burnham Park, a man-made peninsula on the South Side with a stone revetment, swimming cove, and views of the skyline, popular for sunset watching.
• Skokie Lagoons — Walk or kayak the trails around the Skokie Lagoons, a 244-acre nature preserve north of Chicago with seven interconnected lagoons, forest trails, and birdwatching.
• Morton Arboretum trail — Walk the 16 miles of trails at the Morton Arboretum in Lisle, 25 miles west of Chicago, with 4,100 tree species from around the world, a children's garden, and seasonal displays across 1,700 acres.
• Calumet Park — Walk the lakefront at Calumet Park on the far South Side, a 200-acre park with a beach, bike trail, and views of the Indiana Dunes across the state line.
• Cal Sag Trail — Walk or cycle the Cal Sag Trail, a 26-mile paved trail through the southern suburbs of Chicago, passing forest preserves, parks, and the Calumet-Sag Channel.
• Des Plaines River Trail — Walk or cycle the Des Plaines River Trail, a 31-mile unpaved trail along the Des Plaines River from the Chicago city limits to the Wisconsin border, through forest preserves and wetlands.
• Sauk Trail — Walk or cycle the Sauk Trail, a historic Native American trail through the southern suburbs of Chicago, now a paved path connecting parks and forest preserves.
• Chicago 606 — The 606 is a 2.7-mile elevated park and trail system built on a former rail line, connecting four neighborhoods (Logan Square, Humboldt Park, Wicker Park, Bucktown) with access parks and public art.
• Burnham Greenway — Walk or cycle the Burnham Greenway, a 6-mile trail from the South Side of Chicago to the Indiana border, connecting the Calumet area with the Wolf Lake and Eggers Grove forest preserves.