music & nightlife · attractions & tours · outdoor activities ·
Published June 8, 2023
The Best Ways to Spend a Day on the Water in Chicago
With wind in its sails, Chicago is set up for an aquatic summer. ⛵
by Chicago Bucket List
There's no better way to celebrate warm weather than with long days on the water! Whether you’re into getting a party boat on Lake Michigan, spending an afternoon kayaking the lakefront, or viewing the city's coolest buildings along the river, there’s a Chicago aqua-adventure calling your name.
With so many options to choose from, we’ve rounded up some of the most bucket list-worthy water activities from the river to the playpen to experience in Chicago this season.
Chicago's Best Boating Tours and Water Experiences
Lake Michigan Party Boat Cruise
Bring up to two dozen of your friends to cruise Lake Michigan in the ultimate party boat. Enjoy the Bluetooth sound systems, beer pong, and flip cup tables on the deck, and don't forget to hop out and go for a swim on extra hot days! All cruises are BYOB, with fireworks cruises available all summer long.
Where: Chicago Yacht Club: 400 East Monroe Street, Chicago, IL. 60603
Summertime Chi Booze Cruises
This party boat series has a cruise for everyone, no matter how you like to celebrate Summertime Chi. Come on board and enjoy two levels of music and drinking in a climate-controlled setting. See the sights, then turn it up a notch as you head into Lake Michigan with a live DJ. Special events throughout the summer include Sunday Funday Booze Cruises, Firework Cruises, an Independence Day Cruise, and a prime view of the Nascar races coming to Chicago in July.
Where: Summer of George: 900 South Wells Street Chicago, IL
Jet Ski on Lake Michigan
For something a little more high-speed, strap on a life jacket and ride the waves of Lake Michigan on a jet ski. Jet Ski Chicago treats visitors to breathtaking views of the Chicago skyline from the water and offers some of the most powerful vehicles in the industry—boasting 110 horsepower engines—so you can spend an afternoon zooming across the lake. Makes for a fun group outing or an adventurous date idea!
Where: North Ave Beach: 1600 N Lake Shore Drive, Chicago, IL
Happy Hour Kayak Tours
Bring your crew on the most epic happy hour experience in the heart of Chicago! You will embark on an hour-long guided kayak tour downtown while soaking in the skyline views and end the day with a free beverage at Taco Rio!
Where: Urban Kayaks: 435 E. Riverwalk South, Chicago, IL
Lake and River Tiki Boat Cruises
Can you imagine a better way to spend your weekend than cruising through Chicago and enjoying delicious beverages with your favorite people? We can't either! Round up your crew, and get ready to set sail with Island Party Boat. You'll enjoy great views of the city, Island-themed decor and ambiance, and $3 Mimosas and $5 Bloody Marys for you and your party!
Where: Island Party Hut: 355 Chicago Riverwalk, Chicago, IL
Chicago SUP Fireworks Session
Experience Navy Pier’s amazing fireworks from the water in the best way possible: on a board! These paddles embark from North Avenue beach and include instruction along with awesome views of the Skyline and Fireworks show from the water! Great for groups of friends or date nights.
Where: 1603 N Lake Shore Dr, Chicago, IL
Tall Ship Windy
This summer sailing adventure offers spectacular views and an unforgettable day on the water. Choose from a variety of sails, including an afternoon tour featuring true stories of piracy, an evening tour featuring architecture and Chicago's skyline, or even a Pirates Pub Sail where you'll listen and sing to the traditional songs of the pirates!
Where: Navy Pier: Tall Ship Windy 600 E Grand Ave
Wake Surf Lessons
You may not immediately think of surfing when you think of Chicago, but Laketown Surf is bringing the waves to Lake Michigan with its unique wake surfing lessons! As the only wake surf club in the city, Laketown Surf offers a safe and fun experience for surfers of all levels. Single and group options are available and supplied with everything you need to have an amazing day on the water.
Where: Diversey Harbor: 2601 N Cannon Dr, Chicago, IL
Price: Starting at $108 per person
Private Yacht Charters
Rent your own private yacht for the day and take it for a spin on Lake Michigan’s cerulean waters! Knot My Boat Charters offers options ranging from sport cruisers to luxury yachts, so there’s a boat for any and every occasion. Each vessel is equipped with Bluetooth sound systems and multiple entertainment zones. Just bring snacks, drinks, and sunscreen!
Where: 3155 S Lake Shore Drive, Chicago, IL
Fireworks Evening Boat Rentals
If you want to see the Navy Pier Fireworks without the crowds, book an evening tour with up to 9 of your friends and enjoy the show from the water. The two-hour cruise is BYOB and snacks, so feel free to pack up some goodies for the trip!
Where: Chicago Boat Rentals: 1177 N Elston Ave, Chicago, IL
SUP and Sip
The perfect day on the water ends with a refreshing cold drink, and this experience has it built in. Chicago SUP is teaming up with Revolution Brewing to host SUP & SIP events. Swing by after work, relax with a paddle, and refresh with some tastings of Revolution Brewing’s best beers.
Where: 1601 N Lake Shore Dr, Chicago, IL
Chicago Kayak Tours on the River and Lake Michigan
The only thing better than admiring Chicago's architecture while strolling the Riverwalk is admiring it from the Chicago River. Take a historic tour of the city by kayak, and end the night with a fireworks show. Or head to the lakefront and learn paddling basics, or head out for and catch the sunset from the water.
Lakefront Location: 110 N. Lakeshore Dr / Chicago, IL
Riverwalk Location: 435 E. Chicago Riverwalk / Chicago, IL
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