Urban Adventure: Hike, Bike, Climb, Paddle Chicago

Embark on an urban adventure with the best hiking, biking, climbing, and paddling spots in Chicago and throughout Illinois.

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by Jamie Bartosch in Outdoors, Chicago, Activities
September 14, 2018

Courtesy of Brooklyn Boulders

Climbing at Brooklyn Boulders in Chicago

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Chicago has beautiful natural features, but one thing it doesn’t have: elevation. Illinois ranks as one of the flattest states in the U.S. But, that smooth ride is what attracts bikers, paddlers and other outdoor adventure seekers.

Kayak and bike rental places have sprouted up all over Chicago lately, thanks to the Chicago River’s renaissance, most noticeably downtown, and the growing number of bike paths and easy-to-find rentals. Whether you prefer a guided tour, or venture out solo, here are ways to mix in a little urban adventure and exercise with your visit.

Biking in Chicago

Chicago’s Lakefront Path is arguably one of the most beautiful paths in the country with skyscrapers on one side and Lake Michigan beaches on the other with tons of sightseeing like Buckingham Fountain and Navy Pier along the way. For sand and more, North Avenue Beach makes an ideal stop along the 18-mile paved path. Watch intense volleyball games or chess matches or find a seat along the water where sailboats bob in the lake. Be wary of weekend crowds, which jam the path with traffic.

Fun, guided downtown bike tours by Bobby’s Bike Hike help visitors navigate the roads and learn about the city’s history and food (one tour has a deep-dish pizza stop). New night rides end with Navy Pier fireworks.

For a shorter ride through Chicago’s neighborhoods, hop on The 606, an elevated path similar to New York City’s High Line. The straight-line path cuts through trendy Logan Square and Wicker Park, passing new condos, art displays and adorable restaurants, like Miko’s Italian Ice made with fresh fruit.

In the suburbs, find leafy bike paths like the Fox River Trail, which starts in Aurora and heads north through a forest preserve and quaint towns like St. Charles. The waterfall is the star of Darien’s Waterfall Glen, a 9.5-mile loop around Argonne National Laboratory where you can take walking tours of their world-renowned science and engineering facilities. If you’re willing to travel 60 miles southwest of the city, you can ride alongside roaming bison on Midewin Tallgrass Prairie’s bike paths.

Hiking in Chicago

Most hiking is found in state parks, like in the rock formations and waterfalls at Starved Rock State Park in Utica, 90 miles away. But there are a few paths tucked in the city, including the lakefront area at the South Shore Nature Sanctuary. Butterflies flutter around the prairies, woodlands and lily ponds. Migrating birds like the olive green Ruby-Crowned Kinglet populate its small dune habitat. 

Even farther south, on the South Shore Line train stop, find the Indiana Dunes National Lakeshore, where you can hike and climb the towering sand dunes along Lake Michigan with the Chicago skyline in the distance.

Wildflowers and a quiet lake are along the hiking paths at Independence Grove Forest Preserve in north suburban Libertyville, which offers guided hikes on Sundays in the fall months.

Paddling in Chicago

Kayaking through downtown Chicago’s skyscraper canyons is not for the meek. Boat traffic on the Chicago River and windy weather make for a wavy ride. However, it’s an unforgettable, adventure-filled experience that provides a unique view of the city’s stunning architecture. Guided tours by Urban Kayak lead paddlers along various sections of the river, under bridges, and past iconic buildings like the Merchandise Mart. The skyline and architecture tours launch from their new Montrose Harbor location and take place in Lake Michigan. For calmer waters, go in early morning or sunset.

Kayakers, canoeists and stand-up paddleboarders plan day-long trips along the Lake Michigan shoreline – and possibly an overnight camping trip at Illinois Beach State Park in Zion using the Illinois Department of Natural Resources’ Lake Michigan Water Trail map.

The IDNR also hosts a few guided Lake Michigan Water Trail tours (June 30, July 1 and August 3, 2018). Details are available here.

To pedal before you paddle, bike the North Shore Bike Path to the kayak rentals at Skokie Lagoon in suburban Winnetka. You may spot a snapping turtle or muskrat in one of the lagoon’s many nooks.

Climbing in Chicago

Because you can’t legally scale skyscrapers, all of the climbing done in Chicago is indoors. The West Loop’s Brooklyn Boulders is a 25,000 square foot climbing space, surrounded by art, music and a workout gym. The massive climbing walls, some of which require ropes and hooks. Road trip to Savanna, Illinois, along the Illinois-Iowa border, to climb or rappel the 150-foot limestone bluffs at Mississippi Palisades State Park. The state’s best climbing is in its southern tip, in Shawnee National Forest’s Jackson Falls area. There climbers can choose from 60 different climbs on sandstone bluffs and freestanding boulders.


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