With wind in its sails, Chicago is set up for an aquatic summer. ⛵
Published May 03, 2022
There's no better way to celebrate warm weather 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 gone ahead and rounded up some of the most bucket list-worthy water activities to experience in the city.
When the day calls for a summer adventure, Chicagonians can cruise the lakefront, or tour the architecture of the city along the river. Urban Kayaks offers access to both the Chicago Riverwalk and Lakefront locations, with options ranging from twilight and sunset paddles, and “happy hour” paddles that include a domestic brew.
Where: Two locations are available—check your tour package for exact address.
When: Dates Vary
Price: Starting at $40 per person
When the day calls for a summer adventure, Chicagonians can cruise the lakefront, or tour the architecture of the city along the river. Urban Kayaks offers access to both the Chicago Riverwalk and Lakefront locations, with options ranging from twilight and sunset paddles, and “happy hour” paddles that include a domestic brew.
Where: Two locations are available—check your tour package for exact address.
When: Dates Vary
Price: Starting at $40 per person
Bring up to a dozen of your friends to cruise Lake Michigan in the ultimate party boat. Enjoy their bluetooth sound systems, beer pong and flip cup tables on deck. And don’t forget to hop out and swim, to enjoy all the experience has to offer! All cruises are BYOB, with fireworks cruises available all summer long.
Where: Chicago Yacht Club, 400 East Monroe Street, Chicago, IL. 60603
When: Dates Vary
Price: Starting at $1,800 for up to 12 people
Bring up to a dozen of your friends to cruise Lake Michigan in the ultimate party boat. Enjoy their bluetooth sound systems, beer pong and flip cup tables on deck. And don’t forget to hop out and swim, to enjoy all the experience has to offer! All cruises are BYOB, with fireworks cruises available all summer long.
Where: Chicago Yacht Club, 400 East Monroe Street, Chicago, IL. 60603
When: Dates Vary
Price: Starting at $1,800 for up to 12 people
Chicago Fireboat Tours serves as a floating museum, showcasing photographs of the boat in action, firefighting artifacts, and giving a glimpse of what it was like to be a firefighter stationed on the boat. While times are available all throughout the day, we’re big fans of the Sunset Cruise, where you can catch a spectacular Chicago sunset behind the skyline.
Where: DuSable Harbor: 111 N Lake Shore Dr, Chicago, IL. 60601
When: Dates Vary
Price: Starting at $40 per person
Chicago Fireboat Tours serves as a floating museum, showcasing photographs of the boat in action, firefighting artifacts, and giving a glimpse of what it was like to be a firefighter stationed on the boat. While times are available all throughout the day, we’re big fans of the Sunset Cruise, where you can catch a spectacular Chicago sunset behind the skyline.
Where: DuSable Harbor: 111 N Lake Shore Dr, Chicago, IL. 60601
When: Dates Vary
Price: Starting at $40 per person
Live your best “Pirates of the Caribbean” fantasy in the famed Tall Ship Windy! You’ll explore Chicago’s gorgeous shores with a scenic trip around the great Lake Michigan, take in the world-famous skyline, and enjoy a full bar in the aft salon of Windy. And if it suits you better, check out their select firework night cruises.
Where: Navy Pier – Tall Ship Windy, 600 E Grand Ave., Chicago, IL. 60611
When: Dates Vary
Price: Starting around $36 for adults
For more information on Chicago Skyline Sail Aboard Tall Ship Windy
Live your best “Pirates of the Caribbean” fantasy in the famed Tall Ship Windy! You’ll explore Chicago’s gorgeous shores with a scenic trip around the great Lake Michigan, take in the world-famous skyline, and enjoy a full bar in the aft salon of Windy. And if it suits you better, check out their select firework night cruises.
Where: Navy Pier – Tall Ship Windy, 600 E Grand Ave., Chicago, IL. 60611
When: Dates Vary
Price: Starting around $36 for adults
For more information on Chicago Skyline Sail Aboard Tall Ship Windy
Ever find yourself wishing you knew more about the incredible buildings that populate the Chicago skyline? History and architecture enthusiasts alike will appreciate this experience for the knowledgeable tour guides. They will teach you the fascinating history behind Chicago landmarks. A perfect option for visitors or new Chicago residents wanting to learn more about their city. The whole time you will speed around on a RHIB, ex-military boat driven by a Master Class Captain.
Where: J Dock: 1559 E Waldron Dr, Chicago, IL. 60605
When: Dates Vary
Price: Starting at $75 per person
best price
Ever find yourself wishing you knew more about the incredible buildings that populate the Chicago skyline? History and architecture enthusiasts alike will appreciate this experience for the knowledgeable tour guides. They will teach you the fascinating history behind Chicago landmarks. A perfect option for visitors or new Chicago residents wanting to learn more about their city. The whole time you will speed around on a RHIB, ex-military boat driven by a Master Class Captain.
Where: J Dock: 1559 E Waldron Dr, Chicago, IL. 60605
When: Dates Vary
Price: Starting at $75 per person
You may not immediately think of surfing when you think of Chicago, but LakeTown Surf is bringing the waves to Lake Michigan with their unique wakesurfing lessons! As the only wakesurf 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
When: Dates Vary
Price: Starting at $750 for a group of up to six people
For more information on 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 their unique wakesurfing lessons! As the only wakesurf 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
When: Dates Vary
Price: Starting at $750 for a group of up to six people
For more information on Wake Surf Lessons
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