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Rent a Boat or Yacht in Chicago, Illinois

Page 1 of 10239 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
$165/hour
Instant Book
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
$350/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
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
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
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
Luxurious 60' Yacht with Fly Bridge
Events in Chicago · 12 guests

Luxurious 60' Yacht with Fly Bridge

5.0
$450/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
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
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
*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
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
$250/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
$269/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
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
39' Sea Ray for Rent in Chicago, Illinois!
Events in Chicago · 12 guests

39' Sea Ray for Rent in Chicago, Illinois!

5.0
$350+/hour
NEW!!! 35' Luxury Motor Yacht with 4’ swim platform. Get 10% off for Weekend
Events in Chicago · 12 guests

NEW!!! 35' Luxury Motor Yacht with 4’ swim platform. Get 10% off for Weekend

4.7
$180+/hour
Captain Memo's 28 ft. Sea Ray in Chicago
Events in Chicago · 6 guests

Captain Memo's 28 ft. Sea Ray in Chicago

5.0
Superowner
$290/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
LABOR DAY WEEKEND DEAL $250/HOUR & UP ON 40' CRUISER OR 33' BAYLINER
Events in Chicago · 12 guests

LABOR DAY WEEKEND DEAL $250/HOUR & UP ON 40' CRUISER OR 33' BAYLINER

4.8
$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

Chicago Reviews

  1. Mardysa

    Mardysa

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

    I had an amazing time! I booked on rather short notice and Kevin came through for me especially with helping to find a captain for such a busy day. The entire process was smooth and Captain Lisa was great! I’d definitely book with him again in the future.

  2. karina

    karina

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

    Kevin was super nice and accommodating. Any question I asked he answered. Was able to provide me a captain on short notice. The boat itself was super clean! Even the bathroom. And it was a full bathroom. Very happy with purchase and experience. Thank you kevin!

  3. Julian

    Julian

    Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

    I recently had the pleasure of experiencing this boat trip with Captain Z and I can't say enough about how wonderful it was! From start to finish, Captain Z was an exceptional host, making sure every detail was taken care of. The boat itself equipped with everything we needed for a perfect day on water. They were friendly, attentive, and made everyone on board feel welcome and comfortable. We had so much fun exploring the beautiful scenery, enjoying the water and relaxing on the deck. I highly recommend for anyone looking for a memorable and enjoyable boat trip.

  4. 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!

  5. SR

    Sophia

    25.5 ft. Chaparral SSX257 Luxury Vessel

    We had 10 people on the boat, including the captain and a decent amount of stuff and it very comfortably fit everyone and everything! The boat had a great sound system and comfortable seating. Eduard was a great communicator and very helpful in setting up a fun day. Additionally, our captain Diego was awesome!

  6. Michael

    Michael

    25.5 ft. Chaparral SSX257 Luxury Vessel

    Awesome clean boat. Easy to drive and work with and all necessary amenities. Had awesome time at playpen with 5 of my friends but could easily fit a lot more. Eduard was easy to work with and made it a seamless experience.Next time coming to Chicago I will definitely be coming to him if I need a boat for the summer.