Kayaking, walking, boating, biking, — whether you love the sound of a paddle hitting Lake Michigan’s waters, the whir of your bike spokes on a city trail, or the full-throttle roar of a speedboat skimming the lakefront, there’s a whole lot of outdoor adventure waiting for you to Chicago.

Here are some of Chicago’s top spots to enjoy the outdoors.

Walk and bike the Lakefront Trail

(c) Clayton Hauck

Chicago’s iconic Lakefront Trail, which stretches 18.5 miles along Lake Michigan, is lined with beautiful parks, boat harbors, and sandy beaches. It also offers easy access to a variety of top cultural institutions, like Lincoln Park Zoo, Peggy Notebaert Nature Museum, and the South Shore Cultural Center. Plus, the trail is dotted with a variety of scenic waterfront dining options.

Join a guided tour with Bobby’s Bike Hike, which explores lakefront neighborhoods and beaches adjoining the Lakefront Trail. Or grab a Divvy bike as part of the city’s bikeshare program from one of the many Divvy stations across the city, and explore the lakefront at your own speed.

Explore The 606

Get your fitness fix on The 606, an elevated biking, walking, running, rollerblading, and skateboarding-friendly path on Chicago’s northwest side.

The unique path transformed an abandoned railway line into one of the city’s most popular and beautiful outdoor attractions. The paved trail, which rises around 18 feet above street level, is lined with lush greenery, public art, observation areas, and intimate parks.

The trail extends 2.7 miles through four of Chicago’s hippest neighborhoods: Wicker Park, Bucktown, Logan Square, and Humboldt Park. The path is popular with walkers, runners, bikers, and families. You can rent your own set of wheels from a nearby Divvy bike share station or explore the trail on foot.

Kayak on the Chicago Riverwalk

The scenic Chicago Riverwalk is the perfect place to enjoy the outdoors in the heart of downtown.

Head to Urban Kayaks to rent a kayak and glide along downtown’s skyscraper-lined waterfront. You can also take one of their guided tours to learn more about the riverfront architecture. Or hop on one of the many boat tours that depart from the Riverwalk.

Riverwalk seating

The Riverwalk’s 1.25-mile pedestrian stretch consists of a series of coves, where you’ll find bars and restaurants, the McCormick Bridgehouse & Chicago River Museum, public art (including Art on theMART, the world’s largest video-projection art installation), plus walking, biking, fishing, and bird watching.

Swim and play on Lake Michigan

chicago beach guide volleyball

Looking for a sun-soaked getaway? Chicago’s sandy beaches are the perfect place to relax, swim, and enjoy stunning skyline views. Head to popular North Avenue Beachto play a round of beach volleyball, rent a bike, hop on a kayak, or take a spin on a Jet Ski. 

You can also rent stand-up paddleboards, kayaks, Jet Skis, and more at picturesque 31st Street Beach. Chicago Water Sport Rentals will have you out on the water in no time, no matter your experience level. You can try your hand at paddleboard yoga, hop on a banana boat ride, or try a gravity-defying FlyBoard.

Check out our Chicago beach guide for more waterfront activities.

Seadog Cruise at Navy Pier

There are also tons of lakefront cruise options that let you see the city from the water. Adrenaline junkies will love Seadog Cruises’ Lakefront Speedboat Tour, which departs from Navy Pier. For a higher-octane version, complete with sharp twists and turns and 360-degree spins, take Seadog’s Extreme Thrill Ride (be ready to get wet).

For a slower pace, try a leisurely architecture tour from Mercury Sightseeing CruisesShoreline Sightseeing, or Wendella Tours & Cruises. You can get a picture-perfect view of the city skyline on the lake, or cruise through a skyscraper canyon on the Chicago River.

Segway and skate in Grant Park

Segway Tour

Grant Park is a sprawling oasis in the heart of downtown Chicago. Lush gardens bloom with color, creating a beautiful backdrop for the park’s main attraction, Buckingham Fountain, one of the largest fountains in the world. In the summer, there’s a 20-minute water show every hour throughout the day, when the fountain’s center jet shoots 150 feet into the air.

One easy way to cover a lot of ground in the park is with a tour from Absolutely Chicago Segway Tours. If ollies and flips are more your style, let loose at the Grant Park Skate Park. This lakefront course features concrete ramps, grinding rails, quarter pipes, two stair sets, and a gap jump. There are also wheel-friendly courses for BMX bikes, rollerblades, and scooters.

Explore neighborhood parks

Chicago’s many neighborhoods are filled with great green spaces and lots of charm. In Humboldt Park, hop on a vintage swan paddleboat at the historic boat house, then take a walk around the scenic lagoon. Or head to Hyde Park, where you’ll find an authentic Japanese garden and relics from the 1893 World’s Fair in Jackson Park.

If you love venturing off the beaten path, pay a visit to Ping Tom Memorial Park in Chinatown. This 17-acre oasis, complete with pagoda-style pavilion, Chinese landscape design, and impressive river views, is located in the heart of one of the oldest Chinese communities in the country. Make your way to REI Boat House, which offers kayak rentals and classes. You can also take a Chicago Water Taxi all the way from downtown to Ping Tom Memorial Park.

Run, play, and climb in Maggie Daley Park

Maggie Daley Park

Imagine rock climbing, skating, and letting the kids run wild with Lake Michigan and the city skyline as your backdrop. That’s exactly what you’ll find at Maggie Daley Park, part of the Millennium Park campus.

Your first stop should be Maggie Daley Park’s whimsical Skating Ribbon. In the summer, you can travel the winding path with rollerblades or a scooter. In the winter, the ribbon is transformed into a magical ice skating loop.

Rock climb at Maggie Daley Park

Maggie Daley Park also feature a soaring Climbing Wall that reach up to 40 feet. The outdoor climbing park is divided into beginner and advanced spaces, with three types of climbing offered: bouldering, lead-harnessed, and top rope. The park also features a miniature golf course, tennis courts, a sprawling playground, picnic groves, and more.