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Rent a Boat or Yacht in Chicago, Illinois

Page 3 of 11262 listings

Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$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 )

5.0
Best of 2023
$440/hour
27' Chris Craft with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

4.9
Superowner
Best of 2023
$225/hour
31' Sea Ray Romantic or Family or Fun Getaway  Waiting for you !!!
Events in Chicago · 6 guests

31' Sea Ray Romantic or Family or Fun Getaway Waiting for you !!!

5.0
$300/hour
37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen
Events in Chicago · 12 guests

37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen

New
Best of 2023
$250/hour
Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
Powerboats in Chicago · 12 guests

Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht

4.9
Superowner
$300/hour
Downtown Chicago, Party on the Lake!
Powerboats in Chicago · 10 guests

Downtown Chicago, Party on the Lake!

4.9
$270/hour
20 passengers Party Boat in Chicago
Powerboats in Chicago · 20 guests

20 passengers Party Boat in Chicago

5.0
Superowner
Best of 2023
$680/hour
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 2023
$350+/hour
Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL
Events in Chicago · 13 guests

Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL

4.9
$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
Best of 2023
$600/hour
Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
Events in Chicago · 10 guests

Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

4.9
Best of 2023
$180/hour
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
Best of 2023
$250/hour
25ft Rinker - Captained included in price- Chicago
Powerboats in Chicago · 6 guests

25ft Rinker - Captained included in price- Chicago

4.9
Superowner
$160/hour
27 Sea Ray Sundancer DM for October specials
Events in Chicago · 8 guests

27 Sea Ray Sundancer DM for October specials

5.0
$180/hour
46' Spacious Portofino Party Yacht in Chicago For Every Occasion
Events in Chicago · 12 guests

46' Spacious Portofino Party Yacht in Chicago For Every Occasion

4.5
$250/hour
37' Luxury Sailing Yacht in Downtown Chicago
Sailing in Chicago · 7 guests

37' Luxury Sailing Yacht in Downtown Chicago

5.0
Superowner
$200+/hour
Bayliner Ciera Motor Yacht Charter in Chicago, Illinois
Powerboats in Chicago · 10 guests

Bayliner Ciera Motor Yacht Charter in Chicago, Illinois

5.0
Superowner
$200/hour
Burnham Harbor, CAPTAIN/FUEL INCLUDED
Events in Chicago · 7 guests

Burnham Harbor, CAPTAIN/FUEL INCLUDED

5.0
$200+/hour
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
Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago
Events in Chicago · 11 guests

Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago

4.8
$350/hour
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
Powerboats in Chicago · 12 guests

Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

New
$175/hour
Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties
Events in Chicago · 12 guests

Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

5.0
Best of 2023
$250/hour
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Events in Chicago · 5 guests

Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

5.0
Superowner
$200/day

Chicago Reviews

  1. Stephaughn

    Stephaughn

    Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL

    I recently had the pleasure of spending a day aboard this beautiful yacht, and it truly exceeded my expectations. From the moment we arrived, we were welcomed with warm hospitality by a professional and attentive crew. They made sure every detail was taken care of, ensuring our comfort throughout the day. The yacht itself is stunning—luxuriously designed, well-maintained, and spacious enough to accommodate our group comfortably. The interiors are elegant and equipped with every amenity we could possibly need. The outdoor areas are perfect for lounging, dining, and taking in the breathtaking views. Our time on the yacht was both relaxing and memorable, thanks to the crew’s excellent service and the captain’s expertise in navigating the local waters. They took us to the most beautiful and serene spots, making the experience even more special. Overall, our day on the yacht was truly wonderful. I highly recommend this yacht for anyone looking for an unforgettable experience on the water. We’re already looking forward to our next adventure on board.

  2. Frankie

    Frankie

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

    Had a great time ! This boat is amazing and perfect amount of space and luxury feel, we had an amazing time on our team outing and highly recommend to anyone looking for a memorable day out on the Lake/River!

  3. SK

    Sai

    27' Chris Craft with Water Toys plus Jet Ski Available

    Our experience with Captain Tim Jr was incredible! He is a fantastic captain, the boat was awesome, and he battled a storm to get us to the fountain, I proposed to my girlfriend, and he battled the storm right back to the dock. An experience we will never forget, best captain you could ask for!

  4. AC

    Alicia

    37' Luxury Sailing Yacht in Downtown Chicago

    When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!

  5. Roxana

    Roxana

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

    This is the second time I take the boat trip with this company and i have anything bad to say. Our captains went above and beyond Do a big present for your life and take this Amazing adventure i guarantee you nothing but happiness and a great time in that boat, i truly recommend it + Charles and Matt are the best!!!

  6. AS

    Alexa

    Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

    Had an amazing day on the water during the Air and Boat Show with Captain Bob as our guide. He's helpful in giving instructions to the dock, helps set up music and ensures a comfortable and safe experience. Due to his background in the CFD, he knew exactly where to anchor the boat so we could see great views of the air show. It was a worthwhile and memorable experience to share with friends and family!