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Rent a Boat or Yacht in Chicago, Illinois

Page 5 of 12269 listings

Sail in Style: Fuel & Fun Included on 37' Four Winns 348 Vista Yacht!
Events in Chicago · 12 guests

Sail in Style: Fuel & Fun Included on 37' Four Winns 348 Vista Yacht!

4.3
$300hour
Luxury 40 ft. Sea Ray Sundancer Motor Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Luxury 40 ft. Sea Ray Sundancer Motor Yacht in Chicago, Illinois

5.0
$300hour
31' Captained Sea Ray Sundancer, Fun in Chicago Aboard
Powerboats in Chicago · 6 guests

31' Captained Sea Ray Sundancer, Fun in Chicago Aboard

4.8
$250hour
46' Luxury Yacht! Price all inclusive!
Events in Chicago · 6 guests

46' Luxury Yacht! Price all inclusive!

5.0
$350hour
50 ft Double Decker Yacht | Sea Ray Bridge Express
Events in Chicago · 12 guests

50 ft Double Decker Yacht | Sea Ray Bridge Express

New
$100person
61’ Gorgeous Sunseeker Predator Fantastic Condition Weekday Special Rates!
Events in Chicago · 12 guests

61’ Gorgeous Sunseeker Predator Fantastic Condition Weekday Special Rates!

4.7
$250hour
50ft Azimut Luxury Italian Yacht in Chicago, Illinois
Events in Chicago · 12 guests

50ft Azimut Luxury Italian Yacht in Chicago, Illinois

5.0
$550hour
38' Sailing Catamaran, Chicago's Largest!
Sailing in Chicago · 12 guests

38' Sailing Catamaran, Chicago's Largest!

5.0
Superowner
$440-$500hour
Spacious 13 guest 50’ w/swim platform Cruisers Yacht for rent @ 31st Harbor
Events in Chicago · 13 guests

Spacious 13 guest 50’ w/swim platform Cruisers Yacht for rent @ 31st Harbor

5.0
$250-$300hour
50' Sea Ray Sundancer Yacht for 12 Guests in Chicago, IL - Best Value! (MPY#1)
Events in Chicago · 12 guests

50' Sea Ray Sundancer Yacht for 12 Guests in Chicago, IL - Best Value! (MPY#1)

5.0
Superowner
$350hour
32ft SeaRay Sundancer for Charter in Chicago
Events in Chicago · 6 guests

32ft SeaRay Sundancer for Charter in Chicago

5.0
$300hour
26' Formula Yacht Is Ready For Fun in Chicago
Events in Chicago · 12 guests

26' Formula Yacht Is Ready For Fun in Chicago

4.9
$250hour
Classic 20ft Four Winns ($300 For 2hrs Mon-Fri & Sun)(You Capt or Hire a Capt)
Powerboats in Chicago · 6 guests

Classic 20ft Four Winns ($300 For 2hrs Mon-Fri & Sun)(You Capt or Hire a Capt)

5.0
$150day
35' Luxury Motor Yacht with 4’ swim platform in Chicago
Events in Chicago · 12 guests

35' Luxury Motor Yacht with 4’ swim platform in Chicago

5.0
$180-$270hour
36' Sea Ray Cruiser for Charter in Chicago
Events in Chicago · 12 guests

36' Sea Ray Cruiser for Charter in Chicago

4.7
$250hour
37' Spacious Party Yacht For Every Occasion
Events in Chicago · 12 guests

37' Spacious Party Yacht For Every Occasion

5.0
$225hour
Doral Alegria 50' Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Doral Alegria 50' Yacht in Chicago, Illinois

5.0
$400hour
Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago, Illinois
Events in Chicago · 6 guests

Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago, Illinois

5.0
Superowner
$500-$575hour
Immaculate 250 Sea Ray ($600 For 3hrs Mon-Thu & Sun)(You Capt or Hire a Captn)
Powerboats in Chicago · 9 guests

Immaculate 250 Sea Ray ($600 For 3hrs Mon-Thu & Sun)(You Capt or Hire a Captn)

5.0
$200hour
Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
Sailing in Chicago · 4 guests

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

5.0
$202hour
53' Chris Craft Power Yacht in Chicago on Lake Michigan
Events in Chicago · 13 guests

53' Chris Craft Power Yacht in Chicago on Lake Michigan

5.0
$375hour
Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago
Events in Chicago · 6 guests

Experience Luxury and Adventure on a 33' Sea Ray Sundancer Yacht in Chicago

5.0
$250hour
44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!
Events in Chicago · 12 guests

44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!

5.0
$125hour
50' Sea Ray Sundancer (KMB #1) - Perfect for Parties!
Events in Chicago · 12 guests

50' Sea Ray Sundancer (KMB #1) - Perfect for Parties!

4.7
Superowner
$265hour

Chicago Reviews

  1. HB

    Hayden

    Sail in Style: Fuel & Fun Included on 37' Four Winns 348 Vista Yacht!

    Absolutely lovely! Had an amazing time celebrating my 30th birthday. Theresa was incredibly professional and communicative and the captain I chose from her recommendation list was top notch (fun but very professional). Not to mention the boat itself was awesome!

  2. MG

    Mattie

    Sail in Style: Fuel & Fun Included on 37' Four Winns 348 Vista Yacht!

    My friends and I had the absolute best time on this boat this weekend! The boat itself was perfect for our group of 12. Everything was clean and comfortable. We used the lily pad float that they offer and had so much fun on that before heading to watch the fireworks. Theresa promptly answered all my questions leading up to our charter, and that really put me at ease. Would definitely recommend and would definitely book again.

  3. AB

    Ashley

    46' Luxury Yacht! Price all inclusive!

    Terry and his wife made are trip amazing. They were super polite and helpful the whole trip. They took us out on the lake and gave us a nice small tour. We arrived 30 mins late and they were kind enough to still give us our full time. I will be booking with them again.

  4. AA

    Annie

    46' Luxury Yacht! Price all inclusive!

    we had such a wonderful time with Terry and Vanessa on their boat! They were so hospitable, fun, knowledgeable, and low-key. They made sure we had a great time from the minute we got to the boat to the minute we left (we were all sad to leave). It was a magical day on the water - credit to Terry/Vanessa and a perfect sunny day! Definitely going to book with them again; we feel so lucky we met them!

  5. Emily

    Emily

    46' Luxury Yacht! Price all inclusive!

    Truly one of the most amazing experiences I have ever had. If you are looking to tour Chicago in style you HAVE to book this excursion. The views, the boat and the atmosphere are nothing short of stunning, but that’s not even the best part. Terry and Vanessa are a bundle of AWESOME, they truly made the entire trip that much better.

  6. Alfredo

    Alfredo

    46' Luxury Yacht! Price all inclusive!

    Terry and Vanessa were the best! Everything went perfect, couldn’t ask for anything better. They went above and beyond to make sure we were comfortable, took us where we wanted to go, and overall made it a very enjoyable experience. Would definitely go again!