Chicago · IL

Hiking trails near Chicago, IL

165 trails within 75 miles · 24 with detail pages · 80 within 25 miles

This page lists every named hiking trail in our database whose centroid sits within 75 miles of Chicago. Distance is straight-line from the metro center to the trail's centroid; an actual drive to a trailhead may be longer or shorter depending on which end you start from. Multi-state trails (e.g. the Appalachian Trail) appear here if any portion of their length passes within range.

Always check trail conditions, permits, and water sources with the maintaining organisation — National Park Service, U.S. Forest Service ranger district, or trail association. Mountain trails are often impassable for half the year due to snow.

Closest trails to Chicago

Top 5

Illinois · 40 mi

ADT - Illinois - I - Seg 1

26 miles from Chicago · ~45 min

Indiana

Paul H. Douglas Trail through Miller Woods

26 miles from Chicago · ~45 min

Indiana

DLT h - N. Lake to Midwest Rd

28 miles from Chicago · ~50 min

Indiana

Hobart Prairie Grove Trail (West)

30 miles from Chicago · ~50 min

Indiana

Hobart Prairie Grove Trail (East)

31 miles from Chicago · ~55 min

All trails within 75 miles, by distance

165 total

Within 25 miles of Chicago

80 listed
TrailLengthNetworkFrom metroDrive
Horner Park Nature Trail—Local6 mi~10 min
River Bank Neighbors Trail—Local6 mi~10 min
Trailside Museum of Natural History Trails—Local10 mi~20 min
Tan Unpaved Spur—Local11 mi~20 min
Brown Paved Spur—Local13 mi~25 min
Green Paved Spur—Local14 mi~25 min
Brown Unpaved Spur—Local14 mi~25 min
Yellow Unpaved Trail—Local14 mi~25 min
Purple Paved Trail—Local14 mi~25 min
Tan Unpaved Spur—Local15 mi~25 min
Blue Unpaved Spur Trail—Local15 mi~25 min
Yellow Trail Loop2 miLocal15 mi~25 min
Orange Unpaved Trail—Local15 mi~25 min
Green Unpaved Trail—Local15 mi~25 min
Black Trail—Local15 mi~25 min
Purple Unpaved Trail—Local15 mi~25 min
Red Unpaved Trail—Local15 mi~25 min
Black Paved Trail—Local16 mi~25 min
Brown East Trail4 miLocal16 mi~25 min
Black East Unpaved Spur—Local16 mi~25 min
North Island Loop Trail0 miLocal16 mi~30 min
Orange Unpaved Trail—Local16 mi~30 min
Oriole Trail0 miLocal16 mi~30 min
Riverbend Trail1 miLocal16 mi~30 min
Night Heron Trail2 miLocal16 mi~30 min
Monarch Trail0 miLocal16 mi~30 min
Black North Unpaved Spur—Local16 mi~30 min
Tan Trail2 miLocal17 mi~30 min
Yellow East Trail9 miLocal17 mi~30 min
Purple Single Track Loop2 miLocal17 mi~30 min
Farm Pond Trail—Local17 mi~30 min
Purple East Unpaved Spur—Local17 mi~30 min
Black Paved Spur—Local17 mi~30 min
Green East Single Track—Local18 mi~30 min
Tan West Single Track—Local18 mi~30 min
Purple Trail—Local18 mi~30 min
Black Unpaved Trail4 miLocal18 mi~30 min
Blue North Trail—Local18 mi~30 min
Red Paved Trail—Local18 mi~30 min
Green West Single Track—Local18 mi~30 min
Green Unpaved Trail—Local18 mi~30 min
Yellow Loop—Local18 mi~30 min
Green Unpaved Trail—Local18 mi~30 min
Brown Trail—Local19 mi~30 min
Brown West Trail1 miLocal19 mi~30 min
Red North Unpaved Trail—Local19 mi~30 min
Blue South Single Track3 miLocal19 mi~35 min
Yellow West Single Track3 miLocal19 mi~35 min
Orange Unpaved Loop6 miLocal19 mi~35 min
Blue Single Track—Local19 mi~35 min
Black Trail—Local19 mi~35 min
Purple West Unpaved Trail—Local19 mi~35 min
Yellow South Unpaved Trail—Local19 mi~35 min
Blue Trail—Local19 mi~35 min
Tan Trail—Local19 mi~35 min
Red South Single Track2 miLocal20 mi~35 min
Green Trail—Local20 mi~35 min
Yellow Paved Trail—Local21 mi~35 min
Rocky Glen Trail0 miLocal21 mi~35 min
Brown Unpaved Loop—Local21 mi~35 min
Red Unpaved Trail—Local21 mi~35 min
Main Trail10 miLocal21 mi~35 min
Tear-Thumb Trail1 miLocal22 mi~35 min
Orange Unpaved Spur—Local22 mi~40 min
South Field Trail1 miLocal22 mi~40 min
Oldfield Oaks Trail1 miLocal22 mi~40 min
Green Paved Spur—Local23 mi~40 min
Yellow Primitive Loop—Local23 mi~40 min
Black Paved Spur—Local24 mi~40 min
Purple Primitive Trail—Local24 mi~40 min
Orange Primitive Trail—Local24 mi~40 min
Blue Primitive Spur—Local24 mi~40 min
Tan Primitive Trail—Local24 mi~40 min
Tan Paved Spur—Local24 mi~40 min
Purple Paved Spur—Local24 mi~40 min
Blue Paved Spur—Local24 mi~40 min
Brown Primitive Loop—Local25 mi~45 min
Openlands Open Space—Local25 mi~45 min
Yellow Paved Spur—Local25 mi~45 min
Orange Paved Trail—Local25 mi~45 min

25-50 miles

66 listed
TrailLengthNetworkFrom metroDrive
Yellow Paved Loop—Local25 mi~45 min
Brown Paved Spur—Local25 mi~45 min
Brown Paved Trail—Local25 mi~45 min
Fort Sheridan Forest Preserve—Local26 mi~45 min
ADT - Illinois - I - Seg 140 miNational26 mi~45 min
Paul H. Douglas Trail—Local26 mi~45 min
Paul H. Douglas Trail through Miller Woods—26 mi~45 min
Red Maple Allée—Local28 mi~50 min
DLT h - N. Lake to Midwest Rd—Regional28 mi~50 min
Riverwalk—28 mi~50 min
West Beach Trail - Three Loops—Local28 mi~50 min
Tolleston Dunes Trail—Local29 mi~50 min
Portage Lakefront and Riverwalk Trail—Local29 mi~50 min
Hobart Prairie Grove Trail (West)—30 mi~50 min
Hobart Prairie Grove Trail (East)—31 mi~55 min
DLT j - Midwest to Howe—Regional31 mi~55 min
Cowles Bog Trail—Local32 mi~55 min
Dunes Long Trail Alternates—Local32 mi~55 min
Green Belt Trail—32 mi~55 min
Cowles Bog Trail (North)—32 mi~55 min
Little Calumet River Trail—Local32 mi~55 min
Cowles Bog Trail (South)—33 mi~55 min
Bailley / Chellberg Trail—Local33 mi~55 min
Beach Trail—Local33 mi~55 min
Trail 3—Local33 mi~55 min
Trail 4—Local33 mi~55 min
Trail 7—Local33 mi~60 min
Trail 8—Local33 mi~60 min
Nature Center Trail—Local34 mi~60 min
Trail 2—Local34 mi~60 min
DLT n - Howe Rd to Broadway—Regional34 mi~60 min
Trail 9—Local34 mi~60 min
Trail 10—Local34 mi~60 min
East Loop Trail—Local35 mi~1.0 hr
East Loop Trail Loop—Local35 mi~1.0 hr
Glenwood Dunes Trails—Local35 mi~1.0 hr
Dune Ridge Trail—35 mi~1.0 hr
Trout Park—Local35 mi~1.0 hr
Calumet Dunes Trail—35 mi~1.0 hr
Glenwood Dunes Trail (Alternate)—35 mi~1.0 hr
Glenwood Dunes Trail (Main)—35 mi~1.0 hr
Great Marsh Trail (North)—36 mi~1.0 hr
Central Loop Trail—Local36 mi~1.0 hr
Great Marsh Trail (South)—36 mi~1.0 hr
DLT p - Broadway to Mt. Baldy—Regional37 mi~1.1 hr
Ozark Trail390 miRegional37 mi~1.1 hr
Mount Baldy Trails—Local38 mi~1.1 hr
Mt. Baldy Beach Trail—38 mi~1.1 hr
Schweitzer Woods Forest Preserve hiking path—Local39 mi~1.1 hr
Brown Trail—39 mi~1.1 hr
Pink Trail—39 mi~1.1 hr
DLT q - Mt. Baldy to Long Beach—Regional39 mi~1.1 hr
Blue Trail—39 mi~1.1 hr
Red Trail—Local40 mi~1.1 hr
Orange Trail—40 mi~1.1 hr
Yellow Trail—40 mi~1.1 hr
Green Trail—40 mi~1.1 hr
DLT r - Long Beach to New Buffalo—Regional43 mi~1.2 hr
Moraine View Trail2 miLocal43 mi~1.3 hr
Oak View Trail1 miLocal44 mi~1.3 hr
VA Sterne's Woods Trail3 miLocal44 mi~1.3 hr
Prairie View Trail1 miLocal44 mi~1.3 hr
Fen View Trail1 miLocal44 mi~1.3 hr
Kettle View Trail1 miLocal44 mi~1.3 hr
Upland Trail—44 mi~1.3 hr
Galien River County Park Trails—Local47 mi~1.4 hr

50-75 miles

19 listed
TrailLengthNetworkFrom metroDrive
DLT t - New Buffalo to Warren Dunes / Bridgman—Regional50 mi~1.4 hr
Jens Jensen / Pepperidge Trails—Local52 mi~1.5 hr
Harbert Road Preserve—Local53 mi~1.5 hr
Warren Dunes Foot Trails—lcn53 mi~1.5 hr
Sugar Maple Loop—Local54 mi~1.6 hr
Hiking / Ski Trail—Local54 mi~1.6 hr
Nature Loop—Local54 mi~1.6 hr
ADT - Indiana (North) - G - Seg 397 miNational56 mi~1.6 hr
Indian Grass Loop Trail—Local60 mi~1.7 hr
WoodLand Trail—Local60 mi~1.7 hr
Butterfly Weed Loop Trail—Local60 mi~1.7 hr
ADT - Illinois - I - Seg 279 miNational66 mi~1.9 hr
Upland Trail—Local67 mi~1.9 hr
Lowland Trail—Local67 mi~1.9 hr
Wildflower Way—Local67 mi~1.9 hr
Grassland Loop—Local67 mi~1.9 hr
Red Trail1 miLocal70 mi~2.0 hr
Green Trail2 miLocal70 mi~2.0 hr
Yellow Trail2 miLocal70 mi~2.0 hr

Beyond 75 miles

Wider radius

Looking for trails further out? Browse the full Illinois hiking list or jump to all U.S. hiking trails.