An outdoor lover’s guide to Chicago

The beautiful Chicago shoreline. Photo: Shutterstock

The biggest city in the Midwest, and stop number six on GrindTV’s urban road trip series which tells you how to get outside when you’re in an urban area, is better known for its team sports than its outdoor sports.

But the lake, easy access to the rolling prairie outside of the city, and a good variety of state and city parks make Chicago a good place to get some fresh air when you need it most.

Here’s our guide to getting outside in the Windy City.

Cross-country ski

Skiing down Belden Ave. Photo: Victor Grigas wikimedia commons
Skiing down Belden Avenue in Chicago. Photo: Courtesy of Victor Grigas/Wikimedia Commons
In the winter, flat and wide open space makes for good cross-country skiing, so when it snows in the city, you can take your skinny skis out along the lakefront paths. The Forest Preserve District of Cook County trails are all open to skiers, and you can also ski on the public golf courses when it snows.

Mountain biking

Chicago has a surprisingly deep mountain biking community — SRAM is based there — and they say that the closest good riding is in Palos Forest Preserve, southwest of the city.

The former site of the country’s first nuclear reactor now holds more than 50 miles of trails, including winding, technical singletrack and some more mellow doubletrack. It can get crowded, and all the trails have two-way traffic, so keep your head up when you’re riding.

Road biking

Illinois Prairie Path in Chicago. Photo: Dan O'Neill Flickr
The Illinois Prairie Path near Chicago. Photo: Dan O’Neill/Flickr
The Midwest, with its rolling hills, is ideal for road biking. America’s first successful rails to trails conversion is the Illinois Prairie Path, which was turned from railroad line to recreational path in the 1960s.

It starts in Forest Park, on the CTA Blue Line, then winds more than 60 miles through the westerns suburbs.


The Mississippi Palisades, on the bluffs of the Mississippi River, a couple of hours west of the city, is a solid weekend trip for climbers. Most of the climbing is mid-grade top roping on the limestone cliffs.

The most popular zone is called The Cove and requires a spicy scramble to get into. The views of the river, though, are all-time.


Indiana Dunes near Chicago; photo by Diego Delso/Wikimedia Commons
The Indiana Dunes near Chicago. Photo: Courtesy of Diego Delso/Wikimedia Commons
Beach camping isn’t just a coastal thing. Indiana Dunes State Park, just over the Indiana border past Gary, offers up the Midwest’s version.

You can scramble on the 200-foot-high dunes, or hike Mt. Tom or Mt. Jackson before packing it in for the night. In the winter, when it might be too chilly for camping, you can cross-country ski the trails.


You’d never think of Chicago as a hub for triathlon, but it’s got a huge and thriving triathlon community with several clubs that amateurs can take part in to learn the ropes, including Well-Fit Triathlon Training and Multisport Madness, which is the home-club of world junior triathlon champion Lukas Verzbicas.

Chicago also played host to important International Triathlon Union races in 2014 and 2015.

More city guides on GrindTV

An outdoor lover’s guide to Washington, D.C.

An outdoor lover’s guide to New York

An outdoor lover’s guide to Boston

An outdoor lover’s guide to Denver

An outdoor lover’s guide to Seattle

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