Where should I run?
Answer two questions and we'll point you to the right route.
Chicago isn't a city you run through, it's a city you run along. The lakefront, the river, the forest preserves, the old rail lines converted to paths: almost every great run here follows water or history. This guide covers the routes worth knowing, with starting points, trail conditions, and marathon training notes for each.
The Lakefront
Chicago's crown jewelThe Lakefront Trail is what makes Chicago one of the great running cities in the world. An uninterrupted 18.5-mile paved path along Lake Michigan, running from Ardmore Avenue on the north side all the way down to South Shore on the south. Flat, well-maintained, and open year-round.
The north section (Grant Park to Kathy Osterman Beach, ~8.5 miles) passes through Lincoln Park, Belmont Harbor, and Montrose, with stunning skyline views, plenty of company, and run clubs at every turn. The south section (Grant Park to South Shore, ~9 miles) is quieter, less crowded, and ideal for tempo work.
The path is shared with cyclists. Stay in your lane, especially on the busy north stretch. Weekday mornings are far more relaxed than weekend afternoons.
City Paths
Urban routes beyond the lakefrontThe 606 (Bloomingdale Trail)
🛤️A 2.7-mile elevated rail trail running east-west through Wicker Park, Bucktown, Humboldt Park, and Logan Square. Flat, car-free, and always buzzing. Think NYC's High Line, but for runners. Popular with run clubs for tempo repeats and easy shakeouts. The elevation gives you a unique perspective on the neighborhoods below.
Chicago Riverwalk
🌉A scenic run along the south bank of the Chicago River through the Loop, connecting to the Lakefront Trail at the east end. Best for an easy sightseeing run rather than a speed session. You'll be sharing with tourists and stopping for lights. The architectural views are unmatched. Combine with the lakefront north for a solid 10-mile loop from downtown.
North Shore Channel Trail
🌿A tree-lined path running alongside the North Shore Channel from Lawrence Ave north to Evanston. Quieter than the lakefront, partially shaded, and passes through a series of parks with public tracks. The real value: it links directly to the Green Bay Trail at the top, giving you a corridor that runs all the way to the Wisconsin border. Great gateway to a longer point-to-point run via Metra back.
Suburban Rail Trails
The best long-run infrastructure in the Chicago areaIllinois Prairie Path + Great Western Trail
🌾The Illinois Prairie Path is one of the great running trails in the Midwest, a former Chicago Aurora & Elgin railway line converted into a 61-mile crushed limestone network threading through the western suburbs.
The Main Stem (Maywood to Wheaton, ~15 miles) is the anchor. Tree-lined, mostly shaded, and running through the downtowns of Villa Park, Lombard, Glen Ellyn, and Wheaton, each with coffee shops, restaurants, and bars right off the path. Water fountains throughout. Bridges over major roads mean you rarely stop for traffic.
Pair it with the Great Western Trail, straighter, more exposed, fewer amenities, and you have a full marathon-distance loop.
Green Bay Trail
🌲A 6.5-mile trail running through the North Shore suburbs from Wilmette to Glencoe, paralleling the Metra UP-N line. Quiet, tree-lined, and residential. Connects south to the North Shore Channel Trail in Evanston, giving you a corridor that can stretch 15+ miles one-way. The Metra one-way trick works perfectly here: run north, train home.
North Branch Trail
🌳A ~20-mile paved trail following the North Branch of the Chicago River through Cook County forest preserves. Wooded, peaceful, and far less crowded than the lakefront on weekends. Passes through LaBagh Woods, Edgebrook, Bunker Hill, and up to the Skokie Lagoons. Genuinely remote feeling for being inside the city limits.
Des Plaines River Trail
🏞️55 miles of crushed limestone along the Des Plaines River through Cook and Lake County forest preserves. True forest running: river views, wildlife, isolation. Best suited for runners who want to disappear into nature without driving hours. Pick an 8–12 mile section and explore.
Off-Road & Trail
Dirt, hills, and something differentPalos Trail System
⛰️The most genuine trail running experience near Chicago. 40+ miles of dirt and crushed limestone paths through Cook County's Palos Division forest preserves: double and single track, rolling terrain, actual hills, roots, and the occasional mud. Not technical by trail running standards, but a real departure from road running. Universal Sole holds their Trail Challenge series here throughout the year, making it a great introduction if you want a guided first experience.
Route Combinations
Chicago's paths connect. Here are the best multi-route combinations worth knowing.
Lakefront Trail north + Riverwalk west through the Loop + streets back to start. Best city-running loop in Chicago.
North Shore Channel Trail (Lawrence Ave) connects directly to the Green Bay Trail in Evanston. Run north as far as you want. Metra UP-N back from any station.
Illinois Prairie Path Main Stem + Great Western Trail forms a precise 26.2-mile limestone loop through the western suburbs. The training run.
Ardmore Ave (north end) to South Shore Drive (south end). Do it point-to-point. Red Line home from either end. A Chicago rite of passage.
North Branch Trail from Gompers Park through LaBagh, Edgebrook, and Bunker Hill Woods to Skokie Lagoons. Genuinely remote feeling.
Take Metra UP-W to Elmhurst. Run the Prairie Path west to Wheaton, explore the branching network, train home from Wheaton. Zero logistics stress.
Seasonal Notes
Lakefront is plowed but can ice near the water. Prairie Path is ideal, the crushed limestone compacts and drains well in cold. Avoid forest preserve trails after snow.
Palos and forest preserve trails get muddy through April. North Branch blooms beautifully. The lakefront heats up fast, get there early or run south.
Lakefront gets crowded midday. Prairie Path and North Shore Channel offer shade. Start before 7am for anything over 8 miles in July–August.
Peak season. September–October on the Prairie Path and North Branch is stunning. Palos in October for fall color is as good as it gets in the region.
Want More Route Detail?
Worth bookmarking alongside our race calendar and run clubs directory.