Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in Chicago

Search pontoon rentals in Chicago, Illinois.

Page 1 of 1 • 12 listings

24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!
Powerboats in Chicago · 24 guests

24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!

5.0
Superowner
Best of 2026
$800/hour
20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!
Powerboats in Chicago · 20 guests

20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

5.0
Superowner
Best of 2026
$700/hour
24 Guests Captained Party & Event Boat in Chicago with Bathroom & Aqua mat
Powerboats in Chicago · 24 guests

24 Guests Captained Party & Event Boat in Chicago with Bathroom & Aqua mat

5.0
Superowner
Best of 2026
$800/hour
16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!
Powerboats in Chicago · 16 guests

16 Passenger Captained Party & Event 32ft Pontoon Boat in Chicago, Illinois!

5.0
Superowner
Best of 2026
$650/hour
Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour
Powerboats in Chicago · 14 guests

Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour

5.0
Superowner
Best of 2026
$600/hour
Experience Chicago by the water - Rent this 38' Traident Party Pontoon
Powerboats in Chicago · 20 guests

Experience Chicago by the water - Rent this 38' Traident Party Pontoon

5.0
Superowner
Best of 2026
$680/hour
Private Charter 38' Party Pontoon for up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

Private Charter 38' Party Pontoon for up to 20 Guests in Chicago

5.0
Superowner
Best of 2026
$700/hour
No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina
Events in Chicago · 36 guests

No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

5.0
$793/hour
1962 Chris Craft Yacht Charter on the Chicago River!
Events in Chicago · 6 guests

1962 Chris Craft Yacht Charter on the Chicago River!

5.0
$250+/hour
50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package
Powerboats in Chicago · 36 guests

50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package

4.6
$1,350/hour
50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina
Events in Chicago · 24 guests

50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina

5.0
$1,136/hour
Polynesian Party Boat for up to 6 people, Captain and Beverage Credit included
Powerboats in Chicago · 6 guests

Polynesian Party Boat for up to 6 people, Captain and Beverage Credit included

New
$250/hour

Pontoon Reviews in Chicago

  1. Sergio Andres

    Sergio Andres

    1962 Chris Craft Yacht Charter on the Chicago River!

    Albert was amazing! He was very kind, patient, helpful, and attentive throughout the entire experience. He went above and beyond to make our special day unforgettable. We are extremely grateful for his kindness and for such a beautiful experience. We highly recommend him!

  2. EC

    Eleana

    Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour

    We had such a fun time out on the boat for my sisters bachelorette!! Our captains were fun, knowledgeable and gave us some optionality on where we wanted to go and jump in the water. Communication was great and I would absolutely recommend to others!

  3. EZ

    Elizabeth

    No Tie Ups - 50' Corinthian Passenger Boat takes 36 people at Navy Pier Marina

    Perfect day even though it was a rainy one. The whole crew did a great job of anticipating needs and keeping things on track. I'd definitely recommend this to others looking to have a fun day out on the water!

  4. JW

    Jenna

    24 Passenger Captained Pontoon Boat - Fridays and Sunday Fundays in Chicago!

    Could not recommend more!! I booked for a birthday and was so impressed. First off, the customer service was amazing from time of booking to getting off the water. Troy called before and made sure we had any questions answered as well as just general chat about what we wanted the day to look like. Second, we had SO much fun on the water and our captain Jerry, and first mate Hannah were so welcoming and accommodating. They set us all up with games, made sure our drinks were filled, took group photos, and provided such a fun and safe experience. I will be sending all my friends this way because it was truly such an awesome day!

  5. AG

    Ali

    20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

    We booked a 20 person pontoon with Troy for my bachelorette party and he mad the booking process so easy! Then day of Corey and Bree were our captains and were so fun and amazing! Would 10/10 recommend the boat to any group looking for a fun activity :)

  6. KS

    Kailey

    20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

    We booked with Troy for an outing of 20 people and everyone had such a great time! Communication was very easy prior to the trip, having a captain included was huge, they have tables set up for games and food, a speaker system, floaties for the water, and the crew was very helpful! The views were also amazing! Would definitely recommend and would do again