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TravelDestinationsNorth America

The Active Cities Guide to Chicago

The deep-dish pizza might get all the love, but there's plenty to keep you active in the windy city. Here's our guide to the best of it.

Chicago may not be famous for its beaches, but you can't beat seeing that skyline on a run. (Photo: benkrut/Getty Images)

Throughout the pandemic, we'll keep publishing news to help you navigate the state of travel today (like whether travel insurance covers the coronavirus), as well as stories about places for you to put on your bucket list once it's safe to start going more far-flung.

Trail Run

(Photo: Annemod/Flickr)

Des Plaines River Trail

This 55-miler meanders alongside the Des Plaines River through forested open spaces and the heart of the northern burbs. 

Work Out

(Photo: Courtesy of East Bank Club)

East Bank Club

This gym is massive and has exercise classes—from yoga to indoor track cycling—every 30 minutes during peak morning and evening periods. Bonus: the outdoor pool deck has a bar. From $25 per day

Road Bike/Run

(Photo: Eric Allix Rogers/Flickr)

Lakefront Trail

The 18-mile paved path goes through downtown along the edge of Lake Michigan. To up the distance, continue north for six miles to Northwestern University’s campus.


(Photo: Jamie McCaffrey/Flickr)

Chicago River

Rent a kayak and glide through a canyon of skyscrapers. Wateriders rents by the hour and leads evening tours. From $20.


(Photo: MD111/Flickr)

Portage Park and Lake Michigan

On the northwest side of town, Portage Park has an Olympic-size outdoor pool (one-month pass, $25), but we prefer Lake Michigan at Ohio Street Beach, a triathlete favorite.


(Photo: The Wit Hotel Chicago)


This 310-room hotel is in the heart of downtown, just a few blocks from Millenium Park’s running trails. Its open-air rooftop bar draws a crowd of locals on warm nights. From $269.

Gear Up

(Photo: Panu Tangchalermkul/Flickr)

Nike Chicago

Located on the city’s Magnificent Mile, the megastore has Thursday night training runs with multiple distances and provides free gear storage.

(Photo: WBEZ/Flickr)

Bobby’s Bike Hike

You can rent a bombproof commuter bike for $7 a day. But for, say, a GTR Carbon Elite with Shimano 105 components, reserve online with Bobby’s Bike Hike (from $65 per day).

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From Outside Magazine, Jun 2014
Lead Photo: benkrut/Getty Images