Tour My Run!Tour My Run!Chicago is a city you run between the lake and the skyline. Along Lake Michigan, the Lakefront Trail rolls out nearly twenty miles of flat, fast pavement, skyscrapers on one side and open water on the other — from first light, it's where the whole city runs. In the heart of the Loop, the Chicago Riverwalk hugs the water's edge past drawbridges and Art Deco façades, while The 606 (the Bloomingdale Trail) crosses the northwest neighbourhoods on a raised former rail line. On TourMyRun, a local runner takes you along their routes: the Lakefront from Navy Pier, the Lincoln Park loops around the lagoons, the skyline view from Museum Campus and Northerly Island. Not a sightseeing coach, not a random jog around your hotel: one hour of running with someone who lives here, at your pace, who knows the right wind, the right turns and the right tempo.
Come, I'll take you running
To get taken running in Chicago, book a run on TourMyRun: a local runner welcomes you and their group at a meeting point, and you set off along their route, at your own pace, for the length of a run — often around an hour. You never run alone, and there's nothing for you to organise.
📄 Download the Chicago running guide — routes, maps and tips (free PDF)
Get the free guideYour 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.
Looking for someone to run with in Chicago? A local is ready to go. Rather than running alone in a city you don't know, you join a resident who already runs this ground: they open up their route, match the pace to yours, and show you the city on the move.
Not here for the performance? Many guides offer an easy-paced discovery run — a gentle jog, almost at walking pace, to see the city without racing through it. You stop at the viewpoints and take the time to look: it's a way to discover Chicago on the move with a local, at a pace that lets you take everything in.
Yes. On TourMyRun, a run is led by a local who welcomes a small group of runners: you join others — visitors or locals — for a shared group run, without ever having to run alone. It's the group of a TourMyRun run, led by a resident — not an outside club or crew.
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.
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)
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)
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
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
Your guide is a passionate amateur, not a professional. They are not paid: what you pay covers the organisation and a contribution towards the costs they incur — never a wage, never a service contract. It's a run between runners, not a ticketed tour.
Chicago is one of the flattest big cities: the Lakefront Trail, the Riverwalk and The 606 are flat and rolling, ideal for cruising. Every listing shows distance and pace, and your guide adapts the rhythm to your level.
Usually around 1 hour, but it depends on the run you pick — each listing shows distance, duration and pace.
Yes. Chicago guides often offer sunrise slots on the Lakefront and weekday runs — ideal between meetings or before a day of sightseeing. In winter, favour sheltered slots and the milder hours.
Absolutely. If you know your routes by heart and enjoy running with others, you can offer your runs and choose your slots. It's voluntary: your costs are covered, never a wage.
Book a run on TourMyRun: a local runner takes you along their route and matches the pace to yours. You pick a slot, meet them at the meeting point, and run with company.
Yes — every TourMyRun run is led by a local who welcomes a small group. You join other runners for a shared run, and never run alone.
With a resident who knows the city. They open up their routes and their group: you discover Chicago like a local, not like a tourist.
Yes. Some guides offer an easy-paced discovery run, almost at walking pace, with stops at the viewpoints — to see the city on the move, at your own pace.
Search the runs in Chicago on TourMyRun: each listing shows the route, the pace, the duration and the local who guides you. Pick the one that suits you.
Come, I'll take you running
