Chicago Waterfront Fun

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

There’s no better place for groups to enjoy Chicago’s summer weather than on the water, whether it’s along the storied Chicago River or out on the azure waters of Lake Michigan. From touring the Chicago Riverwalk to jet skiing along the lakefront, Chicago offers exciting ways for groups to play on the water.


Chicago Riverwalk ©Ranvestel Photographic

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.

Brush up on your city history at the McCormick Bridgehouse & Chicago River Museum. Enter the historic bridgehouse at river level, where you’ll marvel at the massive gears that power Chicago’s famous Michigan Avenue Bridge. Then make your way five stories up as you learn about the city’s movable bridges and the storied Chicago River.

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, voted one of the top 10 tours in the U.S. by TripAdvisor, 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.

Groups can also set out on the water with a private charter aboard the fun Island Party Boat (rent one with its own water slide!). Get active on a one- or two-hour guided group tour with Urban Kayaks, which travels the Chicago River’s main branch and includes narration of the city’s fascinating history. Or hop aboard the Odyssey Chicago River. Set to open in summer 2018, this single-level, glass-enclosed boat will ply the waters of the Chicago River and offer brunch, lunch and dinner.

City Winery

Stop for a bite to eat at one of the Chicago Riverwalk restaurants. City Winery Chicago Riverwalk is known for its signature wines, Mediterranean paninis and beautiful waterside garden. Get into the tropical vibe of Island Party Hut Tiki Bar and Grill and listen to live island music as you lunch on slow-smoked pulled pork and sip a refreshing fruity cocktail. Or grab a seat under one of the bright yellow umbrella-topped tables and munch on a cheeseburger sided with a vodka lemonade at O’Brien’s Riverwalk Café. At Tiny Tapp Riverwalk, you can pair a gourmet slider with a craft cocktail.


Navy Pier-2

Navy Pier is a lakefront favorite, and one of Chicago’s top attractions. Groups of 20 or more can arrange for 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 with Instagram-worthy views of the Chicago lakefront and skyline. Catch the latest flicks on the massive 3D screen at the AMC Navy Pier IMAX. Listen to free, live music in the seasonal Miller Lite Beer Garden. Or see a show at The Yard at Chicago Shakespeare, a unique new year-round theater venue made up of mobile seating towers that can be configured into a variety of shapes and sizes, accommodating audiences of 150-850 people.

Centennial Wheel at Navy Pier

The recently opened Fifth Third Bank Family Pavilion welcomes guests to Navy Pier with a myriad of local artisans. At the Chicago Children's Museum, kids can do everything from commanding a castle to climbing the rope rigging of a schooner. Cut loose at Pier Park, where kids and adults alike will have a blast on the whimsical hand-painted carousel and Pepsi Wave Swinger®. At the interactive Polk Bros Park, see free outdoor cultural performances on the Lake Stage and City Stage.

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

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 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! Shove off from Navy Pier aboard Tall Ship Windy, a traditional 148-foot-tall topsail schooner that was modeled after a Great Lakes trading ship. The cruise includes maritime storytelling about Lake Michigan’s notorious pirate history.


The scenic Chicago Lakefront Trail stretches for 18 miles along Lake Michigan and is lined with beautiful parks, boat harbors and beaches. Want to hit the waves? Check out these waterfront places where groups can rent everything from kayaks to jet skis.


Kayak Chicago Lake Michigan

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.


Gather the group for stand-up paddleboarding in the picturesque 31st Street Harbor with Chicago Water Sport Rentals. Basic instructions are offered, and equipment rental includes a life jacket, board and paddle. Sign up for the 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.


Jet Skiing on North Avenue Beach ©Adam Alexander Photography

Zoom along the lakefront on a wave runner rental from Jet Ski Chicago, located at North Avenue Beach. 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. Besides riding along the beachfront, you can also buzz by Navy Pier for a breathtaking view from the water. Reservations are recommended, and equipment includes a life jacket (wet suits are available). Jet ski rentals are offered seven days a week until dusk.


Treat your small group of up to six passengers to amazing skylines views aboard a privately chartered sailboat with Come Sailing. Kick back and let the crew man the 36-foot boat during a two-hour cruise (extended tours are also available) that departs from Monroe Harbor. Online reservations are accepted up to one hour prior to scheduled departure times, with the exception of the 8:30am Morning Sail, which must be reserved at least 12 hours in advance.

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