Run Chicago with a local

The must-run routes

• The Lakefront Trail — nearly 18 miles of flat lakeside path on Lake Michigan with the skyline behind you — Chicago's signature route, fast and epic.
• The Chicago Riverwalk & the Loop — right at the river's edge past drawbridges and downtown architecture, a supremely photogenic urban loop.
• The 606 (Bloomingdale Trail) — 2.7 miles of elevated former rail line through Wicker Park, Bucktown and Logan Square, away from traffic.
• Lincoln Park & North Pond — the city's biggest park, its lagoons and shaded paths, an ideal loop for an easy morning endurance run.
• Museum Campus & Northerly Island — on the lakefront by the planetarium and aquarium, the best head-on view of the skyline.

Run like a local

Your guide isn't a service provider — they're a Chicagoan who loves to run and wants to show you their city. They adjust the pace and distance to your level, pick the route to suit the time of day and the lake wind — a quiet Lakefront in the morning, the Riverwalk and the Loop at golden hour — and share the Chicago you won't find in guidebooks. Many of our Chicago guides are running-club members (parkrun, neighbourhood run crews) and sports students who know their training loops by heart. You leave with a real memory — and often a GPX track to run again on your own.

Self-guided routes

Public, well-known routes you can run on your own — a solid plan B to get moving right away. But the best of TourMyRun is still discovering them with a local who takes you, at your pace.

• The Lakefront Trail — Navy Pier heading north≈ 3 miles one-way, flat, extend at will

  A flat paved path along Lake Michigan, with a runners-only lane, heading toward Fullerton and Lincoln Park. The Chicagoans' go-to run — mind the lake wind. A continuous ribbon of nearly 18 miles if you want to go long.

  Start : Ohio Street Beach / Navy Pier (Streeterville)

• The 606 — Bloomingdale Trail≈ 2.7 miles one-way, car-free

  A former rail line turned elevated linear park, from Ashland to Ridgeway, through the hip northwest neighbourhoods. A flat out-and-back away from traffic.

  Start : Damen Ave or Milwaukee Ave access (Wicker Park)

• The Chicago Riverwalk & the Loop≈ 2.5 miles (downtown loop)

  A walk right at the river's edge between drawbridges and skyscrapers, extendable to the lake via the Lakefront Trail. The best of Chicago architecture at running pace.

  Start : Lake Shore Drive / DuSable Bridge, along the Chicago River

• Lincoln Park — North Pond & lagoons loop≈ 4 miles loop

  A shaded loop in the city's largest park, around North Pond and the lagoons, between the zoo and the lakeshore. Perfect for a quiet morning endurance run.

  Start : North Avenue Beach / LaSalle Drive footbridge

How it works

1. 1Search for a run in Chicago and pick a slot that suits you (pace, duration, neighbourhood).
2. 2Book in seconds — the app handles booking, chat with your guide, the GPX track and payment.
3. 3Meet your guide at the meeting point and run. Zero logistics — lace up, we handle the rest.

Upcoming runs in Chicago

• 
  15 km loop along the water in Chicago

  📍 riverside path, Chicago · 72 min

• 
  11 km loop along the water in Chicago

  📍 main square, Chicago · 65 min

• 
  Chicago: 19 km loop along the water

  📍 central station, Chicago · 93 min

• 
  12 km loop along the water in Chicago

  📍 marina, Chicago · 76 min

FAQ — Running in Chicago