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All listings in Chicago

Search pontoon rentals in Chicago, Illinois.

Page 1 of 16 listings

24 Passenger Captained Party & Event Boat in Chicago!
Powerboats in Chicago · 24 guests

24 Passenger Captained Party & Event Boat in Chicago!

5.0
Superowner
Best of 2026
$800/hour
16 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 14 guests

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

5.0
Superowner
Best of 2026
$600/hour
38-ft Party Pontoon for Up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

38-ft Party Pontoon for Up to 20 Guests in Chicago

5.0
Superowner
Best of 2026
$680/hour
16 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 16 guests

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

New
Superowner
Best of 2026
$650/hour
38-ft Party Pontoon for Up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

38-ft Party Pontoon for Up to 20 Guests in Chicago

5.0
Superowner
Best of 2026
$700/hour
Polynesian Party Boat, up to 6 people, captain and drink package included!
Powerboats in Chicago · 6 guests

Polynesian Party Boat, up to 6 people, captain and drink package included!

New
$250/hour

Pontoon Reviews in Chicago

  1. TS

    Tyrese

    38-ft Party Pontoon for Up to 20 Guests in Chicago

    Greg was great I would book again.

  2. EW

    Emma

    24 Passenger Captained Party & Event Boat in Chicago!

    We had a great time on our excursion. They let us pick where we wanted to go and what we wanted to do, and had everything we needed on the boat. The boat itself was clean and safe and had plenty of room for 16 of us to comfortably move around. Would definitely use them again.

  3. LV

    Lizzie

    24 Passenger Captained Party & Event Boat in Chicago!

    Highly recommend this boat experience! Our group had the best time, and everything went according to plan. Capitan Jerry and Stella were super helpful and kept everyone safe, and our group had a really fun time. Highly recommend!!! Communication was clear and set expectations.

  4. NL

    Nora

    24 Passenger Captained Party & Event Boat in Chicago!

    This could not have been a better experience for me and my team! Booking was super easy, cost is fantastic, and the experience was exactly what I hoped. The boat was the perfect says to accommodate us, and Bree and Stella were so kind and fun. We want to go back again with this stellar crew! I would absolutely book with this group again. Thank you for such a fun time!

  5. MH

    Marjorie

    24 Passenger Captained Party & Event Boat in Chicago!

    Dear Captain Chuck and first mate bananas, I truly had the time of my life fighting dragons with you. You men kept the party going with the dranks flowing! Party games galore, lily pad madness, and noodles nonsense <3. Troy, these hero’s deserve raises please send them to Philly so we can do the same in the very clean—not riddled with exoli—schuykill river xoxoxoxo your favorite girls: Jen (bride), MK(trouble), Deanna (belly flop), Cara (real name Mary), Turn up Tori (always turning up), Mandy (and baby pearl), Kaileen (and baby Charlie names after Megan’s dead dog), Megan (life vest queen) Aileen (holding on for dear life ), Marcy (tequila guzzler), and erin (more than a mom)

  6. MB

    Megan

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

    This was our second year doing a boat day with Troy and both years were a blast - we have nothing but great things to say about our experiences! We also got captain Laura two years in a row - she is the absolute best!!! Thanks to Troy, Laura, and Matt for making this day super fun and easy for us. We are already looking forward to next year!