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8 Chicago group outdoor adventures

Looking for fun outdoor activities while your group is visiting Chicago? Here you can kayak the Chicago River, bike along Lake Michigan, and even go rock climbing in the heart of downtown.

We’ve got eight great ideas to help you plan an exciting Chicago outdoor adventure that your group will never forget.

Hit the parks and trail

Rock wall at Maggie Daley Park

Rock climbing in downtown Chicago? It’s a reality at the Maggie Daley Park Climbing Wall. 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 25-100 climbers allowed on the wall at once on a first-come, first-served basis. Or head over to the Maggie Daley Park Skating Ribbon, where you can rent roller blades or scooters at the fieldhouse and whoosh along a landscaped path in the center of Maggie Daley Park.

The Lakefront Trail stretches for 18 miles along Lake Michigan and is lined with beautiful parks, biking and jogging paths, boat harbors, and beaches. Join the Lakefront Neighborhoods Bike Tour hosted by Bobby’s Bike Hike or arrange for a private group tour.

Segway Tour
Absolutely Chicago Segway Tours

Plan a guided group tour with Absolutely Chicago Segway Tours and glide past attractions like Grant Park, a 300-acre oasis in the heart of the city featuring lush gardens. Grant Park’s centerpiece is the beautiful Buckingham Fountain, which features a nightly light show choreographed with music through mid-October.

Get out on the water

Ready to hit the water? Head to the Chicago Riverwalk and get out on the river with Urban Kayaks. First-timers will want to take the Riverwalk Intro Paddle, a one-hour lesson that’s a great option for small groups of paddlers who are new to the Chicago River. For more advanced kayakers, the 1.5-hour Historic Chicago Tour is a guided excursion along the Chicago River’s main branch. Or arrange your own private group outing.

Cruise year round on Odyssey Chicago River. The single-level, European-style dining boat departs from the Chicago River Esplanade, near NBC Tower. Soak in the stunning 360-degree views of the surrounding cityscape as the glass-enclosed vessel glides along the waters of the Chicago River. Odyssey Chicago River is available for full and partial charters, or smaller groups can book a large table for one of the lunch, brunch, dinner, or cocktail cruises.

Navy Pier is one of Chicago’s most popular attractions. Reach for the sky on the Centennial Wheel, riding in temperature-controlled gondolas that soar 200 feet up in the air with Insta-worthy views of the Chicago lakefront and skyline. Discounted tickets for groups of 20 or more are available.

Seadog Cruise at Navy Pier

For the adrenaline junkies in your group, kick things up a notch with Seadog Cruises and its Extreme Thrill Ride. The Seadog speedboat takes off with a jet-propelled blast from Navy Pier, reaching speeds that top 45 mph and making sharp turns and full 360-degree spins along the way. There’s also music and fun narration about the city as you ride. But be forewarned: you will get wet!

If your group includes fans of stand-up paddleboarding (SUP), make your way to the picturesque 31st Street Harbor and Chicago Water Sport Rentals. Basic instructions are offered, and equipment rental includes a life jacket, board, and paddle. More advanced groups can 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.

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