Mobile Menu
Best Ways to Spend a Day on the Water in Chicago
Best Ways to Spend a Day on the Water in Chicago

Best Ways to Spend a Day on the Water in Chicago

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.

Paddleboard or Kayak on the River & Lake Michigan

Paddleboard or Kayak on the River & Lake Michigan

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

For more information on Urban Kayak

location_on Various Locations, CHI

Chicago Kayak Tours on the River and Lake Michigan

$40
book

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

For more information on Urban Kayak

Lake Michigan Party Boat Cruise

Lake Michigan Party Boat Cruise

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

For more information on Lake Michigan Party Boat Cruise

location_on The Playpen, CHI

Lake Michigan Party Boat Cruise

From$1800 $1440 20% off
book

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

For more information on Lake Michigan Party Boat Cruise

Chicago Fireboat Tours

Chicago Fireboat Tours

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

For more information on Chicago Fireboat Tours

best price

location_on DuSable Harbor, CHI

Chicago Fireboat Tours

$37
book

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

For more information on Chicago Fireboat Tours

Chicago Skyline Sail Aboard Tall Ship Windy

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

best price

location_on Lake Michigan, CHI

Chicago Skyline Sail Aboard Tall Ship Windy

From$36 $39 -8% off
book

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

Adventure Tour on an Ex-Military Boat

Adventure Tour on an Ex-Military Boat

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

For more information on Yachti Adventure Tours

best price

location_on Burnham Harbor, CHI

Yachti Adventure Tours

From$84 $75 11% off
  • event Multiple dates
Get tickets now

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

For more information on Yachti Adventure Tours

Wake Surf Lessons

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



best price

location_on Diversey Harbor, CHI

Wake Surf Lessons

From $750
  • event 4/18/22
book

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 Also Like