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Rent a Boat or Yacht in Chicago, Illinois

Page 7 of 12273 listings

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
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
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
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
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
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
Summertime Chi Ready!!
Events in Chicago · 12 guests

Summertime Chi Ready!!

5.0
$325/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
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
$400/hour
Mediterranean Yacht with Fly bridge Boat
Events in Chicago · 12 guests

Mediterranean Yacht with Fly bridge Boat

5.0
$400/hour
SeaRay 310 Sundancer  for Rent on Chicago's Lake Michigan
Events in Chicago · 6 guests

SeaRay 310 Sundancer for Rent on Chicago's Lake Michigan

5.0
$325/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
Spacious 50’ Yacht w/swim platform for rent @ 31st Harbor Charterer + 12 guests
Powerboats in Chicago · 12 guests

Spacious 50’ Yacht w/swim platform for rent @ 31st Harbor Charterer + 12 guests

5.0
$400+/hour
Charter a 33' Ciera Bayliner in Chicago
Events in Chicago · 10 guests

Charter a 33' Ciera Bayliner in Chicago

5.0
$250/hour
42' Luxurious Meridian Flybridge Yacht
Events in Chicago · 12 guests

42' Luxurious Meridian Flybridge Yacht

5.0
$500/hour
Sea Ray 400 Express Cruiser 40ft
Events in Chicago · 12 guests

Sea Ray 400 Express Cruiser 40ft

New
$325/hour
36' Sea Ray Cruiser for Charter in Chicago
Events in Chicago · 12 guests

36' Sea Ray Cruiser for Charter in Chicago

4.8
$350/hour
Experience the Best of Chicago on a 30ft Sea Ray Sundancer
Powerboats in Chicago · 10 guests

Experience the Best of Chicago on a 30ft Sea Ray Sundancer

5.0
$250/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

4.8
$245/hour
No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA
Events in Chicago · 36 guests

No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA

5.0
$793/hour
Luxury 35' Silverton 330 Sport Bridge Yacht Rental in Chicago!
Events in Chicago · 12 guests

Luxury 35' Silverton 330 Sport Bridge Yacht Rental in Chicago!

5.0
$325/hour
Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!
Events in Chicago · 12 guests

Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!

5.0
Superowner
Best of 2025
$400/hour
41' Stunning Sea Ray Yacht - Stunning throughout
Events in Chicago · 13 guests

41' Stunning Sea Ray Yacht - Stunning throughout

5.0
$400/hour
Sea Ray Summer Fun In The Sun!
Events in Chicago · 12 guests

Sea Ray Summer Fun In The Sun!

5.0
$350/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. 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!

  3. KW

    Kierra

    41' Stunning Sea Ray Yacht - Stunning throughout

    Mr Bennett boat was beautiful! He’s very communicative, very kind, and welcoming. The entire process from booking to trip end was seamless. The boat was very clean and spacious. I hosted a summer celebration, my friends and I and had an amazing time! I will only be booking with Norman going forward! 🎉

  4. Mel

    Mel

    33ft Maxum Scr - Your Next Charter Awaits You!

    I booked a charter for 11 people. Captain Mike and crew were incredible. We’re so appreciative of their hospitality. The trip went smoothly and was just a fun time. I’d book again!

  5. Paul

    Paul

    Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!

    Great time! Only advice is to get your captain booked early! So ask them for a list. Cost of $500 is in your fee but need book Captain directly. Tip is usually 20%. Captain Mike was the best!! Trip was a great time for family and friends. Thank you!!!!

  6. JS

    Julie

    No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA

    Captain Tim and first mate Sonny were awesome! I highly recommend, it was very easy, the on boat experience was amazing, and the bride's expectations were exceeded for her bachelorette boat experience!!