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All listings in Chicago

Search yacht rentals in Chicago, Illinois.

Page 1 of 9207 listings

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
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
42FT Regal Commodore Express Cruiser
Powerboats in Chicago · 13 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2025
$245/hour
Stunning 45’ Sea Ray Yacht
Events in Chicago · 12 guests

Stunning 45’ Sea Ray Yacht

5.0
Superowner
$350/hour
Instant Book
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
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
'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
Luxurious 60' Yacht with Fly Bridge
Events in Chicago · 12 guests

Luxurious 60' Yacht with Fly Bridge

5.0
Superowner
$450/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
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
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
Sea Ray Express 390 Luxury Charter in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0
$250/hour
40' Luxury Cruiser Yacht for Charter in Chicago
Events in Chicago · 12 guests

40' Luxury Cruiser Yacht for Charter in Chicago

4.8
$300/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
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
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Events in Chicago · 12 guests

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

5.0
Superowner
Best of 2025
$200/hour
Instant Book
Maxum Yacht 44' in Chicago
Powerboats in Chicago · 13 guests

Maxum Yacht 44' in Chicago

4.9
Superowner
Best of 2025
$268/hour
Li'l Red, Crownline CR250 Cabin Cruiser.
Powerboats in Chicago · 10 guests

Li'l Red, Crownline CR250 Cabin Cruiser.

5.0
Best of 2025
$325/hour
Instant Book
2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
Events in Chicago · 8 guests

2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

5.0
$500/hour
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
Superowner
$300/hour
Instant Book
50' Multi-level Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

50' Multi-level Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2025
$350/hour
Instant Book

Motor Yacht Reviews in Chicago

  1. Nykea

    Nykea

    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

    We had an amazing experience with this boat rental! The team was fantastic—friendly, professional, and very communicative throughout the entire process. The boat itself was beautiful and well-maintained, with a top-notch sound system that made our time on the water even more enjoyable. From start to finish, the service was excellent. We’ll definitely be back again! Highly recommend.

  2. Fidelia

    Fidelia

    Double Decker 50FT Sea Ray Flybridge Yacht!

    My experience with Chris was amazing. We were late due to parking because it was Juneteenth. Chris understood and still had us for the full three hours. He was such an amazing and nice host. Captain Dan Leslie was so cooperative and the best captain we could have. They both made my birthday special and fun. I will return.

  3. Ashley

    Ashley

    28ft. Sea Ray Captained Boat Rental in Chicago

    Captain Memo you were awesome!! Thank you for the charter. The boat was great, you were great, the day was great! If you’re looking for a nice day out on the water with some friends/family look no further. Truly, we highly recommend using Captain Memo. Out of everyone, he was the most responsive and was an overall great person. Our group had a blast with him! Thank you again!!

  4. Daniya

    Daniya

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

    Book Kevin’s boat now! Our captain Hayden was so professional and prompt for our experience. The boat itself is gorgeous and perfect for an all girls getaway . I and my group couldn’t have asked for a better experience.

  5. EL

    Erika

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

    Kevin was easy to coordinate with, got back to me quickly, and the boat was just as pictured. Captain Justin was accommodating and personable. Couldn’t have asked for a better day on the boat! We’ll definitely be coming back!

  6. PD

    Prina

    28ft. Sea Ray Captained Boat Rental in Chicago

    Our party of 4 had a great time on Captain Memo’s boat. He was very communicative and sent a helpful video on where to find the marina. He also took pictures for us and sent them promptly following the ride. He made us feel very safe and welcomed.