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Rent a Boat or Yacht in Chicago, Illinois

Page 4 of 12273 listings

Drive it yourself or hire captain! Affordable sea ray bowrider!
Powerboats in Chicago · 8 guests

Drive it yourself or hire captain! Affordable sea ray bowrider!

4.8
Superowner
Best of 2025
$150+/hour
37' Spacious Party Yacht For Every Occasion
Events in Chicago · 12 guests

37' Spacious Party Yacht For Every Occasion

5.0
$225/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/hour
33ft Day Boat in Chicago
Events in Chicago · 10 guests

33ft Day Boat in Chicago

4.9
$375/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
Superowner
Best of 2025
$275+/hour
New Spacious 40ft Cruisers Yacht for Rent in Chicago
Events in Chicago · 12 guests

New Spacious 40ft Cruisers Yacht for Rent in Chicago

5.0
Superowner
$400/hour
46ft Prestige Flybridge Luxury Yacht in Chicago
Events in Chicago · 13 guests

46ft Prestige Flybridge Luxury Yacht in Chicago

4.9
$400/hour
27' Sea Ray Sundancer – Luxury Cruise with Extended Swim Platform
Events in Chicago · 6 guests

27' Sea Ray Sundancer – Luxury Cruise with Extended Swim Platform

5.0
$250/hour
Summertime Chi Vibes - Soak up the Sun in Style!
Powerboats in Chicago · 6 guests

Summertime Chi Vibes - Soak up the Sun in Style!

5.0
$300/hour
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
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 2025
$400/hour
Do it for Ships N Giggles!!
Events in Chicago · 12 guests

Do it for Ships N Giggles!!

5.0
$300/hour
43ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

43ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
Superowner
$300/hour
42ft Searay Sundancer | Big Boat Small Price!
Events in Chicago · 10 guests

42ft Searay Sundancer | Big Boat Small Price!

5.0
$350/hour
Instant Book
Luxury Sea Ray Sundancer for up to 12 peope
Events in Chicago · 12 guests

Luxury Sea Ray Sundancer for up to 12 peope

4.5
$350/hour
55' Carver Cockpit Motor Yacht -12 Passengers in Chicago, Illinois
Events in Chicago · 12 guests

55' Carver Cockpit Motor Yacht -12 Passengers in Chicago, Illinois

4.8
Best of 2025
$350/hour
Doral Alegria 50' Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Doral Alegria 50' Yacht in Chicago, Illinois

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
$350+/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
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
40ft Formula 40 Performance Cruiser in Chicago
Tours in Chicago · 13 guests

40ft Formula 40 Performance Cruiser in Chicago

5.0
$349/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
Best of 2025
$350/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

Chicago Reviews

  1. RC

    Rachel

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

    It was great! We ended up having a little later departure and they extended our arrival by the amount of time we missed out on from the departure. Really appreciate all the communication and help from James and his crew! Thank you so much, it was so fun!

  2. Pradyu

    Pradyu

    37' Spacious Party Yacht For Every Occasion

    Had a fantastic time on the yacht! Communication and service were excellent throughout, and the captain made everything smooth. The boat was a little rocky, but I’d chalk that up to the conditions of the day. Overall, an amazing day out on the water — would definitely recommend

  3. SL

    Seeta

    Luxury Sea Ray Sundancer for up to 12 peope

    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.

  4. Vanessa

    Vanessa

    43ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

    Kevin is super friendly and made our family day super relaxing and special. His communication was top notch, even providing a video showing where to park in the lot (super helpful!!!), and everything about the experience was great. Would definitely book again. :)

  5. BL

    Brianna

    Summertime Chi Vibes - Soak up the Sun in Style!

    Dan was awesome!! HIGHLY recommend. Very cool yet professional. He was a fantastic captain who made sure we were safe without dampening any of our fun. Thank you, Dan!!! We will be booking again next time we're in Chicago!!

  6. 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.