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All listings in Chicago

Search yacht rentals in Chicago, Illinois.

Page 2 of 9211 listings

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
$350/hour
Instant Book
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
$250/hour
SeaRay Sundancer 340 Motor Yacht
Events in Chicago · 12 guests

SeaRay Sundancer 340 Motor Yacht

3.8
$250/hour
39' Sea Ray for Rent in Chicago, Illinois!
Events in Chicago · 12 guests

39' Sea Ray for Rent in Chicago, Illinois!

5.0
$350+/hour
Instant Book
Burnham Harbor, CAPTAIN/FUEL INCLUDED
Events in Chicago · 7 guests

Burnham Harbor, CAPTAIN/FUEL INCLUDED

5.0
$250+/hour
Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
Events in Chicago · 8 guests

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

5.0
$225/hour
46' Spacious Portofino Party Yacht in Chicago For Every Occasion
Events in Chicago · 12 guests

46' Spacious Portofino Party Yacht in Chicago For Every Occasion

4.6
$250/hour
Instant Book
Double Decker 50ft Sea Ray Flybridge Yacht!
Events in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2025
$292/hour
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Events in Chicago · 20 guests

Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

4.8
$1,500/hour
7 to 13 passenger Lake Michigan Sailing Charter
Sailing in Chicago · 13 guests

7 to 13 passenger Lake Michigan Sailing Charter

5.0
$550/hour
Gorgeous Sea Ray Sundancer 40ft in Chicago with Stunning Interior
Events in Chicago · 13 guests

Gorgeous Sea Ray Sundancer 40ft in Chicago with Stunning Interior

5.0
Superowner
Best of 2025
$245/hour
Sail & Swim from a Luxury Sailing Yacht
Sailing in Chicago · 7 guests

Sail & Swim from a Luxury Sailing Yacht

5.0
Superowner
$150/hour
Instant Book
SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois

4.9
$200/hour
53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois
Events in Chicago · 12 guests

53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois

5.0
Superowner
$375/hour
Instant Book
Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!
Events in Chicago · 12 guests

Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!

4.9
$250/hour
*** $200 to $225 hr***Weekend Charter Rental - 33' Maxum!
Events in Chicago · 8 guests

*** $200 to $225 hr***Weekend Charter Rental - 33' Maxum!

4.9
$175/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
Best of 2025
$300/hour
42' Luxury Mediterranean Yacht - 3 Boats Available!
Events in Chicago · 12 guests

42' Luxury Mediterranean Yacht - 3 Boats Available!

5.0
$350/hour
Instant Book
39' Sea Ray Sundancer - Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

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

5.0
Superowner
$325+/hour
Price Drop!!! Sunday Morning Special!!35' Luxury Motor Yacht
Events in Chicago · 12 guests

Price Drop!!! Sunday Morning Special!!35' Luxury Motor Yacht

4.5
$180+/hour
2010 Sea Ray 450 Sundancer - 45FT Yacht 12 People
Events in Chicago · 12 guests

2010 Sea Ray 450 Sundancer - 45FT Yacht 12 People

5.0
$800/hour
2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
Events in Chicago · 8 guests

2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

5.0
$500/hour
Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
Events in Chicago · 13 guests

Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

4.9
$250/hour
36ft Carver Mariner Motor Yacht in Chicago
Events in Chicago · 12 guests

36ft Carver Mariner Motor Yacht in Chicago

4.8
$350/hour
Instant Book

Motor Yacht Reviews in Chicago

  1. cf

    carolynn

    Sail & Swim from a Luxury Sailing Yacht

    This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)

  2. RJ

    Rachel

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

    Captain Jim and his team went above and beyond to make our charter an unforgettable experience. From the moment we departed to the smooth arrival back at the dock, everything was handled with professionalism, confidence, and a warm, friendly attitude. The boat was immaculate, the ride was smooth, and Captain Jim clearly knew the waters like the back of their hand. They made us feel safe, relaxed, and completely taken care of the entire time. Whether it was pointing out interesting sights, adjusting course for the best views, or making sure we had everything we needed on board, their attention to detail was exceptional. You can tell they truly love what they do—and it shows in the way they connect with guests and manage every aspect of the trip seamlessly. I highly recommend Captain Jim and his team, to anyone looking for a top-tier charter experience. Thank you again for an incredible day on the water!

  3. MA

    Mahab

    46' Spacious Portofino Party Yacht in Chicago For Every Occasion

    Had the best time out on the water with Captain Kyle! He was super professional, friendly, and made sure we felt comfortable and had fun the entire trip. The boat was clean, spacious, and had everything we needed. Kyle knew all the best spots and kept the vibe fun and relaxed. You can tell he really knows what he’s doing and loves what he does. Highly recommend booking with him — can’t wait to go out again!

  4. RS

    Robert

    Double Decker 50ft Sea Ray Flybridge Yacht!

    This motor yacht is a great boat for the Oak St. playpen. We had a terrific time and luckily the weather cooperated! The boat is in great condition and offers multiple lounging areas. The speaker system connected easily and allowed us to listen to all our favorites. Using the backend on the stern we were able to also lounge halfway in the water with some beach chairs. Looking forward to the next time we boat with "Liquid Asset"!

  5. Ari

    Ari

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

    Captain James and Captain John were wonderful hosts. They were clear about procedures and safety that made my group feel really comfortable. The boat was clean and ready for our use. We had a great time at the playpen. I’d definitely book again if in the Chicago area. Thank you again!

  6. Lynnae

    Lynnae

    Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

    Great service great crew great experience! Michael was a very helpful and very nice deckhand! Captain Natalia was very experienced informative and thorough making sure we all made it back safe. Can’t stop hearing “3 points of contact!” in my head lol love it! Will be booking again soon.