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Rent a Boat or Yacht in Chicago, Illinois

Page 1 of 11259 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
$800/hour
20 Passenger Captained Party & Event Boat in Chicago
Powerboats in Chicago · 20 guests

20 Passenger Captained Party & Event Boat in Chicago

5.0
Superowner
$700/hour
28ft. Sea Ray Captained Boat Rental in Chicago
Events in Chicago · 6 guests

28ft. Sea Ray Captained Boat Rental in Chicago

5.0
Superowner
$225/hour
36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Events in Chicago · 6 guests

36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

4.9
$280/hour
27' Maxum 2400 Motor Yacht Rental in Chicago
Powerboats in Chicago · 8 guests

27' Maxum 2400 Motor Yacht Rental in Chicago

4.3
$300/hour
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
Powerboats in Chicago · 12 guests

Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

5.0
Superowner
Best of 2025
$210/hour
42FT Regal Commodore Express Cruiser
Powerboats in Chicago · 13 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2025
$245/hour
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Events in Chicago · 12 guests

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

5.0
$175/hour
'Genius' 40' Sea Ray Sundancer Captained Charter with all amenities in Chicago!
Events in Chicago · 13 guests

'Genius' 40' Sea Ray Sundancer Captained Charter with all amenities in Chicago!

5.0
Superowner
$275/hour
14 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 14 guests

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

5.0
Superowner
$600/hour
Stunning 45’ Sea Ray Yacht
Events in Chicago · 12 guests

Stunning 45’ Sea Ray Yacht

5.0
Superowner
$350/hour
Instant Book
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
$220/hour
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Powerboats in Chicago · 12 guests

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

5.0
Superowner
Best of 2025
$170/hour
Instant Book
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
Events in Chicago · 12 guests

Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!

5.0
$250/hour
Beautiful Yacht 40 LOA 340 Sundancer Searay
Events in Chicago · 13 guests

Beautiful Yacht 40 LOA 340 Sundancer Searay

5.0
$250+/hour
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$250/hour
Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois
Events in Chicago · 13 guests

Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois

5.0
$400/hour
'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!
Events in Chicago · 13 guests

'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!

4.9
Superowner
$275/hour
26 ft. Chaparral SSX257 Luxury Vessel
Powerboats in Chicago · 10 guests

26 ft. Chaparral SSX257 Luxury Vessel

5.0
$200/hour
Luxurious 60' Yacht with Fly Bridge
Events in Chicago · 12 guests

Luxurious 60' Yacht with Fly Bridge

5.0
Superowner
$450/hour
Instant Book
2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025
Events in Chicago · 12 guests

2020 Beneteau GT 42' "James Bond" Yacht — Book Now for Summer 2025

4.7
$400/hour
Instant Book
35' Sea Ray SLX Motor Yacht Charter in Chicago
Events in Chicago · 13 guests

35' Sea Ray SLX Motor Yacht Charter in Chicago

5.0
$250/hour
Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.
Powerboats in Chicago · 6 guests

Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.

5.0
$225+/hour
Double Decker 50FT Sea Ray Flybridge Yacht!
Powerboats in Chicago · 13 guests

Double Decker 50FT Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2025
$292/hour
Instant Book

Chicago Reviews

  1. DC

    Daniela

    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

    We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.

  2. ZD

    Zinnia

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!

  3. KM

    Kasey

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I booked this experience because Nijole had amazing reviews — and now I truly know why. She is talented, no-nonsense host who knows exactly how to make you feel comfortable when you're aboard. We could not have been more grateful or had a better time. Thank you, Nijole! A superstar.

  4. 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.

  5. 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!

  6. Mae

    Mae

    28ft. Sea Ray Captained Boat Rental in Chicago

    5 stars all the way! From booking our excursion to communication on the day of, Memo was great. He gave us the option of cruising down the river or spending more time at the play pen. Was so accommodating and kind. He made our day perfect!