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Rent a Boat or Yacht in Chicago, Illinois

Page 1 of 11263 listings

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
Best of 2025
$175/hour
Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
Events in Chicago · 8 guests

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

5.0
$195/hour
Stunning 45’ Sea Ray Yacht
Events in Chicago · 12 guests

Stunning 45’ Sea Ray Yacht

5.0
$300/hour
25.5 ft. Chaparral SSX257 Luxury Vessel
Powerboats in Chicago · 10 guests

25.5 ft. Chaparral SSX257 Luxury Vessel

5.0
$200/hour
Double Decker 50FT Sea Ray Flybridge Yacht!
Events in Chicago · 13 guests

Double Decker 50FT Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2025
$292/hour
*Embark on a Luxury Lake Michigan Adventure: Rent Our Stunning 2006 Rinker Fiest
Powerboats in Chicago · 8 guests

*Embark on a Luxury Lake Michigan Adventure: Rent Our Stunning 2006 Rinker Fiest

5.0
$225/hour
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
$175/hour
Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago
Events in Chicago · 13 guests

Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago

5.0
$275/hour
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Events in Chicago · 12 guests

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

5.0
Best of 2025
$175/hour
2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024
Events in Chicago · 12 guests

2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024

4.7
$400/hour
Instant Book
Captain Included. Escape the ordinary and cruise on 28’ Sea Ray of fun!
Powerboats in Chicago · 6 guests

Captain Included. Escape the ordinary and cruise on 28’ Sea Ray of fun!

5.0
$225+/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
Stylish elegance and spacious comfort ... your best time ever!
Events in Chicago · 12 guests

Stylish elegance and spacious comfort ... your best time ever!

4.9
$250/hour
Luxurious 60' Yacht with Fly Bridge
Events in Chicago · 12 guests

Luxurious 60' Yacht with Fly Bridge

5.0
$450/hour
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
Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat
Events in Chicago · 12 guests

Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat

5.0
$150/hour
Captained charter on 40' Sea Ray with all amenities in Chicago!
Events in Chicago · 13 guests

Captained charter on 40' Sea Ray with all amenities in Chicago!

5.0
$350/hour
SeaRay Sundancer 340 Motor Yacht
Events in Chicago · 12 guests

SeaRay Sundancer 340 Motor Yacht

3.6
$250/hour
36ft Carver Mariner Motor Yacht in Chicago
Events in Chicago · 12 guests

36ft Carver Mariner Motor Yacht in Chicago

4.8
$300/hour
41' Stunning Sea Ray Yacht - Stunning throughout
Events in Chicago · 13 guests

41' Stunning Sea Ray Yacht - Stunning throughout

5.0
$350/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
$269/hour
45ft Sea Ray 400 EC Big Boat Small Price Everyone Can Enjoy! END OF SUMMER SALE
Events in Chicago · 10 guests

45ft Sea Ray 400 EC Big Boat Small Price Everyone Can Enjoy! END OF SUMMER SALE

5.0
$200/hour
42ft Searay Sundancer | Big Boat Small Price END OF SUMMER SALE!
Events in Chicago · 10 guests

42ft Searay Sundancer | Big Boat Small Price END OF SUMMER SALE!

5.0
$200/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

Chicago Reviews

  1. JY

    Jordan

    Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat

    Jason and Justin did a great job communicating and coordinating our trip. We did 3 hours and then the rain affected our time so we added another hour. Justin was a fun captain and helped us have the best time possible. We definitely recommend renting Jason’s yacht and having Justin as your captain. Will be back for the next season of boating!

  2. SS

    Scarlett

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

    We had a great time! Kevin was very flexible and helped us reschedule easily when the weather did not cooperate. Highly recommend.

  3. Adam

    Adam

    Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

    Had an incredible time out on Kevin’s boat. We had Captain Justin and I couldn’t recommend him enough. We were celebrating a bachelor party and this was the highlight of the weekend!

  4. MM

    Melanie

    Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat

    Jason has very competitive pricing that is well worth it. Communication was very easy. He provided me with a very simple list to find a captain (which was the piece I was most worried about). The boat came with ice and cups which made it so easy for hosting. Had a great time!

  5. KJ

    Kaylan

    Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat

    We had an amazing time on Jason’s boat celebrating a 30th birthday! Our captain Justin was phenomenal. Everything was just as it was on the listing. Boat was clean, as was the bathroom. Ice and coolers were provided as well as kitchen utensils. An amazing deal comparatively. Wouldn’t change a thing! Thank you Jason and Justin!

  6. MF

    Maddie

    Stunning 45’ Sea Ray Yacht

    We rented out this yacht for my boyfriend’s birthday party! The boat was spacious and just as described. Our captain Peter and his wife were an amazing crew, thorough with safety, attentive, and went above and beyond to make sure that we had an incredible time! Booking with Eugene was a breeze, he was quick to respond, as well as answered every question that I asked! Everyone had a blast, and we will definitely be booking through them again!