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Chicago, Illinois Boat Rentals & Yacht Charters

Page 4 of 11258 listings

36ft Carver Mariner Motor Yacht in Chicago
Events in Chicago · 12 guests

36ft Carver Mariner Motor Yacht in Chicago

4.9
$350/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
62' $2M Italian Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

62' $2M Italian Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2026
$800/hour
Instant Book
61’ Gorgeous Sunseeker Predator Weekday Special Rates
Events in Chicago · 13 guests

61’ Gorgeous Sunseeker Predator Weekday Special Rates

4.9
Superowner
$280/hour
Sea Ray 48' Chicago Playpen, River, Winery, Lilly Pad
Events in Chicago · 12 guests

Sea Ray 48' Chicago Playpen, River, Winery, Lilly Pad

5.0
Superowner
$375+/hour
Limited Availability
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
Superowner
Best of 2026
$400/hour
Instant Book
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)
Events in Chicago · 12 guests

38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

5.0
Superowner
$250/hour
50' Sea Ray Sundancer - 12 Passengers in Chicago, Illinois
Events in Chicago · 12 guests

50' Sea Ray Sundancer - 12 Passengers in Chicago, Illinois

4.9
$350/hour
Doral Alegria 50' Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Doral Alegria 50' Yacht in Chicago, Illinois

5.0
$225/hour
40ft Formula 40 Performance Cruiser in Chicago
Tours in Chicago · 13 guests

40ft Formula 40 Performance Cruiser in Chicago

5.0
$349/hour
Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser
Events in Chicago · 12 guests

Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser

5.0
$300/hour
Explore the Famous Chicago Playpen! - 46ft Sea Ray
Events in Chicago · 12 guests

Explore the Famous Chicago Playpen! - 46ft Sea Ray

5.0
Superowner
Best of 2026
$400/hour
Instant Book
55' Sea Ray Luxury Yacht in Chicago
Events in Chicago · 12 guests

55' Sea Ray Luxury Yacht in Chicago

5.0
$375+/hour
SeaRay 330 Motor Yacht Charter in Chicago, Illinois
Events in Chicago · 12 guests

SeaRay 330 Motor Yacht Charter in Chicago, Illinois

5.0
$200/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200/hour
Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht
Powerboats in Chicago · 6 guests

Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht

5.0
$375/hour
42ft Searay Sundancer | Big Boat Small Price! End of Summer Discounts!
Events in Chicago · 10 guests

42ft Searay Sundancer | Big Boat Small Price! End of Summer Discounts!

5.0
$300/hour
Stunning 105ft Denison Party Yacht in Chicago
Events in Chicago · 30 guests

Stunning 105ft Denison Party Yacht in Chicago

4.7
$1,450+/hour
Set Sail on a Spacious 42' Silverton Yacht
Powerboats in Chicago · 12 guests

Set Sail on a Spacious 42' Silverton Yacht

5.0
$300/hour
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

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

5.0
Superowner
Best of 2026
$300+/hour
Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois
Powerboats in Chicago · 8 guests

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

4.6
$275/hour
44ft Regal Luxury Yacht On Lake Michigan!
Events in Chicago · 12 guests

44ft Regal Luxury Yacht On Lake Michigan!

5.0
$275+/hour
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

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

5.0
Superowner
Best of 2026
$300+/hour

Chicago Reviews

  1. AM

    Abigail

    Sea Ray 48' Chicago Playpen, River, Winery, Lilly Pad

    Our group had an amazing time!! Will 100% book again!

  2. AR

    Allaina

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

    My friends and I️ had an amazing time on Alonzo's boat. Alonzo was incredibly helpful during the booking process, and was able to quickly answer all of my questions. The boat was beautiful and we had a lot of fun. I'll definitely be rebooking soon!

  3. Ryan

    Ryan

    62' $2M Italian Luxury Yacht with Party up to 12

    The yacht was incredible and was everything shown in the pictures. Captain Rez did a tremendous job, was very social and outgoing, and clearly had a impressive amount of captaining knowledge. This was perfect for our corporate outing and we will definitely be renting again! Thank you!

  4. Toi

    Toi

    62' $2M Italian Luxury Yacht with Party up to 12

    Loved this yacht! It is beautiful & spacious. My guests thoroughly enjoyed. Captain Rez made the experience exceptional. I will book again. Side bar: the captain fee is separate not included at least as it was shown when I booked. Ask before booking.

  5. AD

    Ash

    61’ Gorgeous Sunseeker Predator Weekday Special Rates

    Brett's boat was exactly as described. We fell in love with it the moment we stepped on it. 4 hours just flew by :) On top of that he had amazing recommendation for hiring the Captain, who made the entire trip well worth it. We were 12 adults and there was plenty of room for everyone to sit, move around, and, most importantly, dance :P We'd definitely rent this boat if we get the opportunity again.

  6. Ricardo

    Ricardo

    61’ Gorgeous Sunseeker Predator Weekday Special Rates

    Just want to say a big Thankyou! To Mr. Feivey & gang. I booked 3 months in advance and had to reschedule dates. They were very accommodating and pleasant to work with. The ride was fantastic and the water was perfect temperature. This is my second time renting the “Sex Sea” and it was a great time per usual.