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With Captain
Lively, feel-good cruises in Chicago where groups celebrate birthdays and parties, enjoy smooth planning, and relax at fun anchor spots together.
Spacious party-style pontoon that comfortably fits larger groups, with guests noting it was easy to gather, relax, and enjoy time together on board.
Consistently praised for smooth communication, easy coordination, and a friendly crew that finds great spots and keeps the outing running effortlessly.
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AI Overview
Owner's Description
ABOUT THE TRIP Celebrate on the water with a private charter in Chicago! Perfect for bachelor and bachelorette parties, birthdays, corporate events, or even wedding ceremonies, this pontoon offers a fantastic way to enjoy the city from a unique perspective. Choose to cruise through the Chicago River, marvel at the city’s iconic landmarks, or anchor in the Playpen for a fun-filled day of swimming and relaxation. ABOUT THE BOAT This 2016 Traident Trident pontoon is 38 feet long and fully equipped for group outings. It features a full-sized bathroom, a powerful Bluetooth sound system, and floating party mats for added fun. With spacious seating and an oversized cooler stocked with ice, this boat is designed for comfort and entertainment. WHAT'S INCLUDED Your booking includes access to all onboard amenities, including the bathroom, sound system, and floating mats. Ice is provided, and you are welcome to bring your own food and drinks. WHAT'S NOT INCLUDED Food, drinks, and additional services are not included. OTHER THINGS TO KNOW You can choose from three trip options: Prime Time (11 AM – 2 PM), Afternoon (3 PM – 6 PM), or Evening (7 PM – 10 PM). You can coordinate specific needs and itinerary details with the owner after booking to ensure your outing is exactly as you envision.
Captain Greg
565 total bookings
Superowner
Best of 2026
- Capacity
- 20 guests
- Powerboats, Pontoons, & RIBs
- Pontoon
Reviews
(101 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
45 photos have been added by reviewers who booked this listing.
TS
Tyrese
Greg was great I would book again.
Thomas
Thanks for making this an incredible experience with my best friends! Everything went smooth and communication was perfect. 5/5 would book again !
Macy
Would definitely reccomend for large groups, great experience with pong tables for games, pads to float on and lots of room for 20 people. Captain greg was great as well
Emily
The boat was so spacious and the experience was so fun! The waves were pretty strong that day but the captain did a great job of controlling the boat. They were so patient with my party as we were late but still gave us a time to remember!
Chelsea
Our group had a great time. I love that we have the option to travel along the river or go to the playpen. There was plenty of space and it was just a great way to relax!
Captain Greg
565 total bookings
Superowner
Best of 2026
For over 6 years our we have specialized in fully customizable events aboard our commercial pontoon vessels . Every detail is customized to meet our client's objectives. Each detail will not be overlooked when you treat your guests to the stunning Chicago skyline setting aboard.
Features & Details
- Traident
- Trident
- Capacity: 20 people max
Safety Equipment
Life Jackets (1)
Guest Amenities
Toilets (1)
Leisure & Entertainment Equipment
Bluetooth
Sound System
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
400 E Monroe
Chicago, Illinois, 60601
United States
Departure Location
Cancellation Policy
Free cancellation up to 30 days before your trip.
Additional Terms & Information
The boat is Ideal for • Sunset trips • Playpen party in Chicago scene • River Trips • Bachelor and Bachelorette party • Wedding ceremony by Captain Additional Services: • Birthday • Anniversaries • Family reunions • Team Building • Showers/Rehearsals • Graduation Weather Policy: If weather is bad or waves over 3 feet there will be no refund ,you will be able to reschedule anytime as long it does not interfere, with a charter that was schedule on that date.We are very flexible and easy to work with.
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