We Found These Experiences For You (18)
Boat Tour and Illinois
22 FT Private Pontoon Cruise - 2 Hours
Starting at $350 | Cruise the Chicago river for 2 hours!
Enjoy cruising the beautiful Chicago River for 2 hours The 22 ft pontoon has more space and a table for snacks and drinks. BYOB and food or allow us to cater so you have less to carry. You are the driver. Our crew will give you or someone in your group a lesson when you arrive Gas Powered, automatic. ...
Chicago
2 Hours
Private Tours
Boat Tour, Pontoon Boat Rental
Chicago Boat Rentals
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Annual VIP Membership
$250 • 50% off pontoon rentals for the season, yacht discounts, VIP perks
When purchased, members receive: -50% off any size pontoon rental -$100 off yacht rentals -Access to member-only events -No fee for cancellations and reschedules After membership is purchased, an exclusive code will be emailed. The code is exclusive to the customer who purchased and can be used to receive ...
Chicago
Private Tours
Boat Tour, Cruise / Large Boat
Chicago Boat Rentals
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18 FT Private Pontoon Cruise - 2 Hours
Starting at $150 | Cruise the Chicago river for 2 hours!
Enjoy cruising the beautiful Chicago River for 2 hours You are the driver! Our dock crew will train you or someone in your group when you arrive. Gas Powered, automatic. simple to drive. BYOB and snacks are welcome or we will be happy to cater to you. Although our boats have bluetooth capabilities, we ...
Chicago
2 Hours
Private Tours
Boat Tour, Pontoon Boat Rental
Chicago Boat Rentals
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Evening Boat Rentals (Fireworks )
Starting at $400 | 2 sizes available
Enjoy cruising the beautiful Chicago River for 2 hours. This cruise includes the famous firework show located next to Navy Pier. This offer is available only Wednesday and Saturday nights, Memorial Day through Labor Day. You are the driver! BYOB or we can cater Lifejackets provided (under 13 must be ...
Chicago
2 Hours
Boat Cruise, Boat Tour, Cruise / Large Boat, Evening Cruise, Fireworks Cruise, River Cruise, Sternwheeler/Riverboat
Chicago Boat Rentals
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Private Boat Tour
For all ages! • 2.5 Hours
Join Dave for a cruise on the Chicago River in your own private vessel for up to 10 people. Learn about the Chicago skyline and how innovative architecture shaped the city and changed the world. Ditch the herd with the microphone and the same old speech for an interesting local perspective and find out ...
Chicago
2.5 Hours
Private Tours
Boat Tour
Chicago by Dave
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Historical and Architectural Lake & River Tour
April 2026-November 2026
???? Discover Chicago by Water: History, Architecture & Firefighting Legacy Step aboard and let our expert docents guide you through the fascinating story of Chicago—told from the best seat in the city: the deck of our historic fireboat. ???? World-Famous Architecture Marvel at Chicago’s skyline ...
Chicago
90m - 2hrs
Boat Tour
Chicago Fireboat Tours
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51? Sea Ray Sundancer Powerboat
All Ages • 3 to 8 Hours • Up to 12 People
An incredible boating experience! Duration Three to Eight Hours About The Yacht has a huge front of the boat that can fit the entire group plus a sun pad. The back seating area of the boat has a plenty of room and turns into a lounger. She is a two bathroom, two bedroom sailboat with a great dining and ...
Chicago
Boat Tour
Chicago Sailboat & Yacht Charters
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Day Cruise (Endless Summer)
For all ages! • 3-6 Hours • Up to 13 Guests
Welcome aboard the luxurious 32 ft Larson Cabrio, a spacious cabin cruiser designed for ultimate comfort and enjoyment. Relax in a cozy bedroom, prepare meals in the fully equipped kitchen, and freshen up in the convenient bathroom. Our amenities include two fridges to keep your refreshments cool and ...
Chicago
3-6 Hours
Boat Tour
Endless Summer Chi
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The Chicago River Cruise
For all ages! • 3-6 Hours • Up to 13 Guests
Embark on a captivating journey through the heart of the Windy City with a unique Chicago River cruise! Discover hidden gems and gain an entirely new perspective as you navigate the bustling waterways, where architectural marvels rise majestically along the banks. Imagine gliding past the lively Chicago ...
Chicago
3-6 Hours
Boat Tour
Poseidon Chicago Charters
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Day Cruise
For all ages! • 3-6 Hours • Up to 13 Guests
Set sail with Poseidon Chicago Charters for an unforgettable daytime experience on the magnificent Lake Michigan! The Chicago skyline provides a stunning backdrop to your special occasion. Whether you're celebrating a momentous bachelor or bachelorette party, marking a milestone birthday, orchestrating ...
Chicago
3-6 Hours
Private Tours
Boat Tour
Poseidon Chicago Charters
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USVI Full Day
Best of the USVI • Fuel Included
Adventure in Style aboard Salty Viking! Explore the US Virgin Islands in complete comfort on Salty Viking, where every detail of your private, all-inclusive day on the water is tailored to you. Designed with expansive seating throughout, she’s ideal for families and larger groups. Stretch out on the ...
Cruz Bay
Private Tours
Boat Tour, Snorkeling
Salty Viking
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Independence Day Weekend Kick Off Sail
All ages • 2 Hours • Best View in the City Aboard 148 foot Schooner Windy
Duration 2 Hours About A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town! Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July ...
Chicago
Boat Tour
Tall Ship Windy
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Fireworks Cruise!
All ages • 90 Minutes • Great for friends & family!
Duration 90 Min. The Wednesday Fireworks Boat Tour starts promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm. About A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely ...
Chicago
Boat Tour
Tall Ship Windy
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Traditional Chicago Blues ~LIVE~ with Michael Charles!!
All ages • 2 Hours • Chase your Monday BLUES away!
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer. About We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the ...
Chicago
Boat Tour
Tall Ship Windy
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Chicago Skyline Sail
All ages • 75 Minutes • Great for friends & family!
Duration Each sail is approximately 75 minutes. About AVAILABLE NOW SAIL DAILY MAY THROUGH OCTOBER 1! Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from ...
Chicago
Boat Tour
Tall Ship Windy
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2026 Air & Water Show - Special Event!
All ages • 2.5 Hours • Great for friends & family!
Duration 2.5 Hours About An experience you don’t want to miss! Chicago’s famous Air and Water Show aboard the 148? Lakeshore Sail Charters is truly a magical event. While the official schedule has yet to be announced, we anticipate another year of thrill and excitement. We’ll leave our dock from ...
Chicago
Boat Tour
Tall Ship Windy
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Fireworks Cruise!
A Chicago tradition aboard the Official Flagship of the City of Chicago
Duration 90 Min. The Wednesday Fireworks Boat Tour starts promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm. About A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely ...
Chicago
Boat Cruise, Boat Tour, Cruise / Large Boat, Evening Cruise, Fireworks Cruise, Sailing
Tall Ship Windy
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Chicago River Cruise
Ages 21+ • 1-3 Hour Private Cruises • Discover Chicago from a Vintage Motorboat!
Private Vintage Motorboat River Cruise: Discover Chicago from the Water Experience Chicago from a whole new perspective with a private cruise aboard a beautifully restored 1962 vintage motorboat. Glide past iconic landmarks like Centennial Fountain, Navy Pier, and the Chicago Harbor Locks, all while ...
1-3 Hour Options
Private Tours
Boat Tour
Vintage Yacht Charters
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