You’ll find loads of fun group water activities in Chicago on scenic Lake Michigan and the winding Chicago River.


Warm summer weather is wholeheartedly embraced in Chicago. And there’s no better place to enjoy it than on the water, whether it’s along the storied curves of the Chicago River or out on the azure waters of Lake Michigan. From biking along the lakefront to kayaking the river surrounded by skyscrapers, Chicago offers some of the most exciting ways for groups to play.



Kayaks along the Chicago Riverwalk

Head down to the south bank of the Chicago River and explore the pedestrian-friendly Chicago Riverwalk, which stretches from Lake Shore Drive to Lake Street. Here you’ll find water activities, sightseeing cruises, outdoor dining and amazing river views. Groups can set out on the water with a private charter aboard the fun Island Party Boat (rent one with its own water slide!) or get a guided tour with Urban Kayaks (the 1.5-hour Historic Chicago Tour travels the Chicago River’s main branch and includes narration of the city’s fascinating history).

Chicago Architecture Foundation River Cruise

There are also plenty of sightseeing boats to choose from, including Wendella Sightseeing Boats, Mercury, Chicago’s Skyline Cruiseline, Chicago Line Cruises or the Chicago Architecture Foundation Center River Cruise Aboard Chicago’s First Lady Cruises, one of the city’s most popular architecture cruises, which passes more than 50 architectural gems along the Chicago River. A cost-effective and quick way to take a cruise is via Chicago Water Taxi, which loops around seven docks on the river, making stops from downtown to Chinatown.

City Winery at Chicago Riverwalk

Stop for a bite to eat at one of the waterside restaurants, including City Winery Chicago Riverwalk, with its signature wines, Mediterranean paninis and beautiful waterside garden; steak sandwiches and vodka lemonade at O’Brien’s Riverwalk Café; and Tiny Tapp Riverwalk, known for its gourmet sliders and craft cocktails.



Navy Pier

Navy Pier is a lakefront favorite, and one of Chicago’s top attractions. Navy Pier offers groups of 20 or more discounted tickets to Navy Pier-produced events and attractions, plus Food Court Certificates that provide a selection of meal options at various Navy Pier eateries. Reach for the sky on the Centennial Wheel , riding in temperature-controlled gondolas that soar 200 feet up in the air. Catch a cool 3-D flick at the AMC Navy Pier IMAX theater. Or see a show at the Chicago Shakespeare Theater. Opening in fall 2017, The Yard at Chicago Shakespeare Theater will be a unique year-round theater venue, made up of mobile towers that can be configured into a variety of shapes and sizes, accommodating audiences ranging from 150-850 people.

Mystic Blue Boathouse

Arrange for a group lunch or dinner cruise aboard the Spirit of Chicago or Odyssey Lake Michigan (formerly Odyssey Cruises). Or head out on one of the late-night moonlight cruises aboard Mystic Blue, with a DJ and dance floor. Set sail on an architecture or nighttime fireworks cruise (Wed. and Sat. evenings during the summer) with Shoreline Sightseeing. Or hop on a Shoreline Sightseeing Water Taxi for an easy and economical way to reach the Museum Campus, which lets you off right at the Shedd Aquarium.

Seadog Cruises Chicago

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 45mph and making sharp turns and full 360-degree spins along the way. There’s also music and a fun narration about the city as you ride. But be forewarned: you will get wet!



Chicago Lakefront Trail

The scenic Chicago Lakefront Trail stretches for 18 miles along Lake Michigan and is lined with beautiful parks, boat harbors and beaches (Oak Street and North Avenue are great for people watching). Take time to sun on the sand at 31st Street Beach or gather the group for stand-up paddle boarding in the harbor with Chicago Water Sport Rentals. Don’t miss Northerly Island, a manmade peninsula that juts into Lake Michigan and features nature paths for strolling, as well as the outdoor Huntington Bank Pavilion that hosts big-name summertime concerts.

Bobby's Bike Hike Chicago

Rent some wheels and join the Lakefront Neighborhoods Bike Tour hosted by Bobby’s Bike Hike, with private group tours available. Or glide along the waterfront with Absolutely Chicago Segway Tours. Choose the Chicago Lakefront Museum Campus Tour or opt to have a private tour specially customized for your group.


Photos top to bottom: Chicago Riverwalk; Chicago Architecture Foundation River Cruise Aboard Chicago's First Lady Cruises: City Winery Chicago Riverwalk; Navy Pier; Mystic Blue; Seadog Cruises; Chicago Lakefront Trail; Bobby's Bike Hike

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