Climb, bike and paddle without ever leaving the city.

The fresh air, the sun on your back, the city buzzing with energy—there’s a lot to love about outdoor adventures in Chicago. Whether you prefer the sound of a paddle hitting the Lake Michigan waters, the whir of your bike spokes on a city trail or the full-throttle roar of a jet ski skimming the lakefront, we’ve got just the thing to get your heart pounding. 


Climbing wall at Maggie Daley Park in Chicago

Rock climbing in downtown Chicago? It’s a reality at the Maggie Daley Park Climbing Wall, located right next to Millennium Park. The soaring wall, complete with sculptural rocks and boulders, forms Chicago’s only climbing park. Reaching a maximum height of 40 feet, the wall is divided into beginner and advanced spaces with three different types of climbing: bouldering, lead-harnessed and top rope. Between 25-100 climbers are allowed on the wall at once, on a first-come, first-served basis. Climbing equipment is available for rental.

If you would rather keep your feet on the ground, head over to the Skating Ribbon, where you can rent a pair of roller blades or a scooter at the fieldhouse and whoosh along a landscaped path in the center of Maggie Daley Park.


Absolutely Chicago Segway Tours

Hop on board with Absolutely Chicago Segway Tours and glide effortlessly through Grant Park, a 300-acre oasis in the heart of downtown Chicago. Lush gardens blooming with colorful flowers dot the park, but the main attraction is the centerpiece Buckingham Fountain. Unveiled in 1927, the ornate fountain festooned with sea horses is one of the largest in the world. Catch the nightly display of colored lights and music choreographed with the fountain’s dancing waters through mid-October.

If sick tricks like Ollies and flips are more your style, let loose at the Grant Park Skate Park. This nearly two-acre lakefront course features concrete ramps, grinding rails, quarter pipes, two stair sets and a cool gap jump. There are also wheel-friendly elements for BMX bikes, rollerblades and scooters. 


Walking and biking the Chicago Lakefront Trail in Lincoln Park

The Chicago Lakefront Trail stretches for 18 miles along Lake Michigan and is lined with beautiful parks, biking and jogging paths, boat harbors and beaches (Oak Street and North Avenue are great for people watching). Join a guided tour with Bobby’s Bike Hike and peddle along the scenic path, which spans from the south to the north sides of the city. 

THE 606

The 606 Chicago

Cruise over to The 606, an elevated, 2.7-mile bike-friendly path winding through four of Chicago’s hippest neighborhoods: Wicker Park/BucktownLogan Square and Humboldt Park. You can rent wheels from a nearby Divvy bike-share station. 


Kayak Chicago

Want to hit the waves? Head to North Avenue Beach or Montrose Beach on Lake Michigan to rent a kayak from Kayak Chicago. Several different guided tours are offered, from architectural and sunset paddles to a Navy Pier fireworks float. Kayak Chicago also offers stand-up paddleboard (SUP) rentals. All kayak and SUP rentals include a personal flotation device and instructional paddle talk before heading out on the water.

If you’re a fan of SUP make your way to the picturesque 31stStreet Harbor and Chicago Water Sport Rentals. Basic instructions are offered, and equipment rental includes a life jacket, board and paddle. If you’re more advanced, sign up for a one-hour SUP Yoga class that begins with stretching on land before heading out to the blue waters of Lake Michigan. Besides SUP, Chicago Water Sport also rents jet skis and kayaks.

Zoom along the lakefront on a rental from Jet Ski Chicago. Located at the popular North Avenue Beach, Jet Ski Chicago rents powerful Yamaha VX110 Wave Runners. With the stunning Chicago skyline as your backdrop, jump the choppy waves or motor out to the Playpen (a no-wake zone and popular meeting spot for boaters just off Oak Street Beach) for a smooth water cruise. Jet ski rentals are offered seven days a week until dusk.

Featured Partners

More Outdoor Fun