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Rent a Boat or Yacht in Chicago, Illinois

Page 6 of 11262 listings

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
$350/hour
40’ Cruiser Yacht Charter for fun, music and you bring the action!
Events in Chicago · 12 guests

40’ Cruiser Yacht Charter for fun, music and you bring the action!

4.4
$300/hour
31ft Sea Ray Motor Yacht Charter in Chicago, Illinois
Events in Chicago · 12 guests

31ft Sea Ray Motor Yacht Charter in Chicago, Illinois

5.0
$300/hour
New to Chicago! One of Kind Charter Boat
Powerboats in Chicago · 13 guests

New to Chicago! One of Kind Charter Boat

5.0
Superowner
$325/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Best of 2025
$375+/hour
50ft Spectacular Luxury Italian Unique Yacht
Events in Chicago · 13 guests

50ft Spectacular Luxury Italian Unique Yacht

5.0
$300/hour
Enjoy the Sun with Family or Friends on a 58' SeaRay Sundancer
Events in Chicago · 12 guests

Enjoy the Sun with Family or Friends on a 58' SeaRay Sundancer

5.0
$350/hour
Lake Michigan Chicago Yacht Party – 40' Luxury Sea Ray for Up to 12 Guests
Events in Chicago · 12 guests

Lake Michigan Chicago Yacht Party – 40' Luxury Sea Ray for Up to 12 Guests

5.0
$225/hour
Cruise on the New & Luxurious 2024 Chaparral 30' Yacht!!!
Events in Chicago · 10 guests

Cruise on the New & Luxurious 2024 Chaparral 30' Yacht!!!

5.0
$275/hour
Chicago Boat Cruise on Captained Sea Ray Sundancer 260 Motor Yacht
Events in Chicago · 8 guests

Chicago Boat Cruise on Captained Sea Ray Sundancer 260 Motor Yacht

5.0
$275/hour
33ft Maxum Scr - Your Next Charter Awaits You!
Events in Chicago · 12 guests

33ft Maxum Scr - Your Next Charter Awaits You!

5.0
$300/hour
Limited Availability
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
$300/hour
Instant Book
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

5.0
Superowner
Best of 2025
$200/hour
Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat
Powerboats in Chicago · 12 guests

Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat

New
$250/hour
Instant Book
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Powerboats in Chicago · 12 guests

41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
$390+/hour
Luxury 54 Foot Sea Ray Sundancer Yacht for Charter
Events in Chicago · 12 guests

Luxury 54 Foot Sea Ray Sundancer Yacht for Charter

5.0
$500/hour
Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay
Events in Chicago · 12 guests

Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay

5.0
$400/hour
63ft Premier Sea Ray Chicago Playpen, River, Winery
Events in Chicago · 12 guests

63ft Premier Sea Ray Chicago Playpen, River, Winery

5.0
Superowner
$700/hour
SeaRay 320 Sundancer Yacht -  31st Street Harbor Beach Playpen Chicago
Events in Chicago · 12 guests

SeaRay 320 Sundancer Yacht - 31st Street Harbor Beach Playpen Chicago

5.0
$250/hour
37' Luxury Carver Multi-Level Yacht w/ Premium Sound
Events in Chicago · 12 guests

37' Luxury Carver Multi-Level Yacht w/ Premium Sound

5.0
$275/hour
Enjoy Chicago in this 46' Sea Ray - Great for Birthdays - Bachelorette Parties
Events in Chicago · 12 guests

Enjoy Chicago in this 46' Sea Ray - Great for Birthdays - Bachelorette Parties

5.0
Superowner
Best of 2025
$200/hour
Mediterranean Yacht with Fly bridge Boat
Events in Chicago · 12 guests

Mediterranean Yacht with Fly bridge Boat

5.0
$400/hour
End of Summer Deal!! $1000 for 3 hours
Events in Chicago · 12 guests

End of Summer Deal!! $1000 for 3 hours

4.5
$350/hour
40 foot Luxury Cruiser
Events in Chicago · 12 guests

40 foot Luxury Cruiser

5.0
$250/hour

Chicago Reviews

  1. Katey

    Katey

    Cruise on the New & Luxurious 2024 Chaparral 30' Yacht!!!

    Frank was an incredible host for this boat- such a beautiful boat with a luxurious feel. He was very accommodating, communicative, and he just exuded kindness and honesty- the kind of person you'd feel comfortable paying this much money to! He even brought a trolley to help carry our coolers. They also had coolers on the boat- which was so helpful and unexpected. We had such a great time on the boat. HIGHLY recommend.

  2. SL

    Seeta

    End of Summer Deal!! $1000 for 3 hours

    We had am amazing time at the Air & Water show. Communication with Kadir was prompt and accurate. The Captain Emir was a super star, I would definitely recommend them. The boat is as pictured perfect for a party of 10. The whole process from start to finish was seamless.

  3. DH

    Danielle

    SeaRay 320 Sundancer Yacht - 31st Street Harbor Beach Playpen Chicago

    From start to finish, I had a 5 star experience. Kat made booking easy, was extremely accommodating, and responsive! The vessel was clean, and just as photoed. Captain Derek was personable, professional and a good time. If you find yourself in Chicago, book with “Owner”, they rock!

  4. SE

    Sabrine

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

    So stunning, and a TON of fun! You get a little tour of Chi and a ton of pic opportunities and then a good amount of time to swim or paddle board. So amazing and definitely will book again!

  5. KM

    Kacy

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

    If you’re looking for a reliable and luxury charter for the day in Chicago - you absolutely need to book Rick. They showed us the best time and made us feel so comfortable. We had never been to Chicago before and they knew all the best spots and catered to what our vibe was. 10/10 experience.

  6. ME

    Melissa

    Enjoy the Sun with Family or Friends on a 58' SeaRay Sundancer

    I can’t say enough about Dana and her crew. Exceptional service, amazing communication, and perfect boat for hosting and playing in the play pen. I would highly suggest Dana to anyone looking for a fun day out on the water.