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Rent a Boat or Yacht in Chicago, Illinois

Page 1 of 11262 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
44' Sea Ray Express Luxury Motor Yacht Rental in Chicago
Events in Chicago · 13 guests

44' Sea Ray Express Luxury Motor Yacht Rental in Chicago

4.8
$349/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
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
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
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
42FT Regal Commodore Express Cruiser
Powerboats in Chicago · 13 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2025
$245/hour
Beautiful Yacht 40 LOA 340 Sundancer Searay
Events in Chicago · 13 guests

Beautiful Yacht 40 LOA 340 Sundancer Searay

5.0
$250+/hour
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
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
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
$200/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
Downtown Chicago, Party on the Lake!
Powerboats in Chicago · 10 guests

Downtown Chicago, Party on the Lake!

5.0
Best of 2025
$230/hour
26 ft. Chaparral SSX257 Luxury Vessel
Powerboats in Chicago · 10 guests

26 ft. Chaparral SSX257 Luxury Vessel

5.0
$200/hour
Instant Book
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
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
Powerboats in Chicago · 12 guests

Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

4.7
Superowner
Best of 2025
$210/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
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
33' Formula Motor Yacht - Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht - Great for Playpen!

5.0
$250/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
24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches
Powerboats in Chicago · 5 guests

24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches

5.0
$200/hour

Chicago Reviews

  1. BM

    Bianca

    26 ft. Chaparral SSX257 Luxury Vessel

    Mark provided all details and answered all questions super-fast the listing was as described he made the whole process easy and smooth, and Eduard was a great Captain as well. Had an amazing time and will be booking again HIGHLY RECOMMENDED for bookings.

  2. Julia

    Julia

    Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

    Definitely recommend booking with Jason. The booking process and communication leading up to our reservation was top notch. My group had an amazing time and the boat was beautiful! Captain Jimmy was also great and made sure we were taken care of. Looking forward to booking with Jason again in the future.

  3. Amy

    Amy

    26 ft. Chaparral SSX257 Luxury Vessel

    Marks boats are exactly as advertised. The boat was immaculate and so easy to operate. He is quick to answer any and all inquiries leading up to and during the excursion if needed. This is my 2nd time using his boat and we will be regular customers.

  4. Beatris

    Beatris

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

    My experience booking with Jason was a 10/10 through and through from beginning to end. The entire process was seamless, from booking the boat rental to the actual boat day. Jason provided great communication and answered all of my questions promptly. The boat itself was even better than I imagined, very beautiful with a lot of space, very clean and well kept. The captain that was recommended was a great time and really took care of us. I thoroughly enjoyed my entire experience and will be booking with him again!

  5. CW

    Claire

    Beautiful Yacht 40 LOA 340 Sundancer Searay

    Great boat rental! Very affordable, and captain provided a cooler and lots of floaties to use in the playpen. Captain and owner were both super responsive leading up to the booking. Boat was well maintained, clean and lots of sitting space both inside and outside. Will definitely be booking again!

  6. Carina

    Carina

    Beautiful Yacht 40 LOA 340 Sundancer Searay

    Had a great 1st experience chartering this boat. Owner Peter was communicative and helpful through the process. Everything was thought of for our trip and we appreciated the amenities provided! It was smooth sailing for us and we will definitely book again.