Bucket Listers

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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 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.

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

Stand Up Paddleboarding with Views of the Fireworks

Get ready for an evening session of stand up paddleboarding on the iconic North Avenue beachfront, with unobstructed views of the Navy Pier Fireworks. This 1-1/2 hour experience invites you to bring your own snacks, wine, and blankets to relax and watch the sky light up after your time on the water is finished.

Where: Pick Up Location: North Avenue Beach: 1601 N Lake Shore Dr. Chicago, IL 60614

When: Multiple dates and times 

Price: $59 per person on Bucket Listers (originally $75)

For more information on stand up paddleboarding amongst the fireworks.

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

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

Party Under the Fireworks on a Yacht Cruise

Go on a two-floor fireworks yacht cruise! The “Hell or Highwater” yacht cruise takes you on a sail on the riverways and lakefront of Chicago, with a stunning display of fireworks at your back. The yacht’s open-air upper deck has a disco dance party theme and the lower deck is dedicated to the Goth sounds of the underworld. There will be additional special themed nights on July 1 and July 30. 

Where: Dusable Harbor: 200 N. Breakwater Access, Chicago, IL

When: Saturday, May 28: Hell or Highwater

Friday, July 1: Theme Night

Saturday, July 30: Theme Night

Price: Starting at $45 per person 

For more information on Auris Presents Yacht Cruises: Hell or Highwater.


Summer Mondays with Stand Up Paddleboarding and Beer Tasting

Come wind down on your Monday night with Chicago SUP and Revolution Brewing. Enjoy an evening stand up paddle boarding session on the water followed by beach time sampling one of the best Chicago-based beers in the city. It’s a great way to fight off any beginning-of-the-week scaries. 

Where: Pick Up Location: North Avenue Beach: 1601 N Lake Shore Dr. Chicago, IL 60614

When: Various Mondays, 6 p.m. - 7:30 p.m.

Price: $35 per person on Bucket Listers (originally $40)

For more information on Sup & Sip Summer Mondays.

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

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

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