Cookies!

We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.

20 passengers Party Boat in Chicago

With Captain

5.0(80 reviews)

220 bookings

the United States,Illinois,Chicago,Powerboats

We are a fully certified by the U.S. Coast Guard. And our trained staff waits to serve you. So let your worries be ours. Experience the great day on the water in Chicago, Illinois by boat! Charter the Pontoon for up to 20 passengers Rates: • Prime 3 hours (11am - 2pm ): $2,400.00 • Afternoon 3 hours ( 3pm -6pm ): $2,200.00 • Evening 3 hours ( 7pm - 10pm ): $2,100.00 What To Expect Onboard: The boats have a full-size bathroom, a little bar for servings drinks, two tables, a powerful sound system with Bluetooth connectivity, and an outlet to charge the phone. If you like swimming, we can anchor the boat in a designated area (playpen), and you can enjoy the water using our provided floating party mats. If you’d instead enjoy views of majestic Chicago landmarks, we offer a scenic river tour option as well. 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 • Wedding ceremony with Captain • Showers/Rehearsals • Graduation

Captain Greg

462 total bookings

Superowner

Best of 2025

Capacity: 20 guests

Powerboats, Pontoons, & RIBs: Pontoon

Reviews

5.0 (80 reviews)

Listing Accuracy
Awesome
Departure & Return
Awesome
Vessel & Equipment
Awesome
Communication
Awesome
Value
Awesome
Itinerary & Experience
Awesome

22 photos have been added by reviewers who booked this listing.

Serena

Greg made our boat trip perfect for my friend’s bachelorette. Everything was exactly as described and the service was awesome! We spent the day on the playpen and got to see some amazing views of the city. Would definitely book with Greg and crew again!
MC
Megan

Our boat day with Captain Greg was easily the best day of summer 2022! We had the most amazing time and the entire experience from booking to the trip couldn't have been better. The communication was wonderful, planning was so easy, and the boat was exactly what we were hoping for and more. Highly recommend a boat day with Captain Greg! We will definitely be booking again in the future. THANK YOU SO MUCH!
SG
Sandra

We had such a great time! I celebrated my birthday with a group of 20, it couldn't have been better. Captain and his wife were so fun, we went around the PlayPen. There were swimming mats and noodles provided for us along with a large cooler with ice. They both enjoyed the fun with us by dancing to music and encouraging photos! Such sweet people. Highly recommend!
Jennifer

Would definitely book again; so easy to communicate and had such a great time with Captain Greg and crew. Boat is exactly as described and the crew helped us deflate all our inflatables at the end of the trip so we could continue enjoying ourselves on the ride back to the harbor. Great boat for a large group!
SA
Steven

The crew was great, the boat was perfect for our group of 20 and we had a perfect day. We cruised the river and the Chicago skyline, capped off with swimming on a perfect day. The boat is great for a big group like ours and the staff is super nice, accommodating and knowledgeable. Total pros. We will definitely be back with our team next year! Five stars!

Captain Greg

462 total bookings

Superowner

Best of 2025

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

Make: Traident
Model: Trident

Length: 38ft

Year: 2016

Fuel type: Gas
Single Engine
Wheel steering
Head
Music System
Charter
Toilet
Outboard Engine

Approximate Location

You’ll get directions to the departure location when you make a booking.

Cancellation Policy

Full refund up to 30 days prior.

Additional Terms & Information

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.