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Chicago, Illinois Boat Rentals & Yacht Charters

Page 6 of 12 • 266 listings

Now to End of Season Discount! All Included! 42 Sea Ray Sundancer Pure Luxury.
Events in Chicago · 10 guests

Now to End of Season Discount! All Included! 42 Sea Ray Sundancer Pure Luxury.

5.0
$300/hour
50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo
Events in Chicago · 13 guests

50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo

5.0
$375/hour
See the Gorgeous Chicago Skyline & Experience Lake Michigan on 33' Sea Ray Yacht
Events in Chicago · 12 guests

See the Gorgeous Chicago Skyline & Experience Lake Michigan on 33' Sea Ray Yacht

5.0
$275/hour
60ft Azimut Evolution Double Decker Yacht Charter in Chicago
Events in Chicago · 13 guests

60ft Azimut Evolution Double Decker Yacht Charter in Chicago

5.0
Superowner
Best of 2026
$750+/hour
New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain
Powerboats in Chicago · 13 guests

New to Chicago! One of Kind Charter Boat - Fjord 44 Open with USCG Captain

4.6
Superowner
$275/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!

4.5
$300/hour
Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht
Events in Chicago · 6 guests

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

5.0
$375/hour
Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain
Sailing in Chicago · 6 guests

Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

5.0
$450/hour
Luxury 40ft Maxum 3700 SCR Motor Yacht Available To Cruise To The Playpen!
Events in Chicago · 12 guests

Luxury 40ft Maxum 3700 SCR Motor Yacht Available To Cruise To The Playpen!

4.8
$250/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
Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht
Events in Chicago · 13 guests

Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht

5.0
$175/hour
30ft Sea Ray Sundancer Motor Yacht - The Best of Chicago
Events in Chicago · 10 guests

30ft Sea Ray Sundancer Motor Yacht - The Best of Chicago

5.0
$200/hour
Now to End of Season Discount! All Included! 45 Sea Ray Sundancer Pure Luxury.
Events in Chicago · 10 guests

Now to End of Season Discount! All Included! 45 Sea Ray Sundancer Pure Luxury.

5.0
$300/hour
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

5.0
$175+/hour
Catch a summer vibe on the water aboard 39' Sea Ray motor yacht
Events in Chicago · 12 guests

Catch a summer vibe on the water aboard 39' Sea Ray motor yacht

5.0
$225/hour
Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests
Events in Chicago · 12 guests

Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests

5.0
$300/hour
Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht
Events in Chicago · 12 guests

Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht

5.0
Superowner
Best of 2026
$325/hour
"Captain is Free". If you have 6 passengers or less...this yacht is Just Right!!
Events in Chicago · 6 guests

"Captain is Free". If you have 6 passengers or less...this yacht is Just Right!!

5.0
$350+/hour
46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46' Azimut Quartano Motor Yacht Rental in Chicago, Illinois

4.8
$400/hour
Luxury 40' Sea Ray Sundancer Motor Yacht with Premium Sound System in Chicago
Events in Chicago · 12 guests

Luxury 40' Sea Ray Sundancer Motor Yacht with Premium Sound System in Chicago

5.0
$300/hour
33ft Maxum Scr Motor Yacht - Your Next Charter Awaits You!
Events in Chicago · 12 guests

33ft Maxum Scr Motor Yacht - Your Next Charter Awaits You!

5.0
$250/hour
Enjoy the Sun on Lake Michigan with Family or Friends on a 58' Sea Ray Yacht
Events in Chicago · 12 guests

Enjoy the Sun on Lake Michigan with Family or Friends on a 58' Sea Ray Yacht

5.0
$375/hour
Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests
Events in Chicago · 12 guests

Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests

5.0
Superowner
Best of 2026
$160+/hour
60ft Tiara Luxury Yacht – Chicago
Events in Chicago · 12 guests

60ft Tiara Luxury Yacht – Chicago

5.0
$650/hour

Chicago Reviews

  1. KT

    Ken

    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests

    Captain Mike is AMAZING!! He was incredibly accommodating, patiently waiting for our late arrivals and working with us to chart the perfect route so we could hit every spot on our list. Even through choppy waters, he expertly handled the boat to ensure a smooth and comfortable ride, all while keeping safety his top priority. An exceptional captain and host—he’ll absolutely be our first choice for our next outing!

  2. Tatyana

    Tatyana

    Now to End of Season Discount! All Included! 45 Sea Ray Sundancer Pure Luxury.

    Girls boat day was a success with captain Anthony and Mike!! The boat was spacious, clean, and perfect for our group of 10. Plenty of room on the vessel for all of us to roam around and enjoy a day in the Playpen. Communication was seamless with captain Anthony and made sure we were all set for our trip. Highly recommend and will def be booking again!

  3. JP

    Joon

    Now to End of Season Discount! All Included! 42 Sea Ray Sundancer Pure Luxury.

    Captain Anthony and his crew were amazing and provided my group and I an experience we will never forget! They were very professional and safety-oriented while being easy going and making sure everyone was comfortable and safe. He educated us about the water and kept an eye on everyone in my group. Everyone had a wonderful time and we will definitely be booking through him again. The marina at navy pier is also small compared to other nearby harbors which makes it very easy to find the boat and load and unload things. It’s also minutes away from the playpen so you will have no time wasted!

  4. Brittany

    Brittany

    50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo

    We rented the yacht for our friend’s 30th birthday bash and had an amazing time! Everyone associated with the boat, along with our captain, was so helpful and nice. We could not have asked for a better experience! Make sure to bring some ice for the cooler along with you. And know that there is an opportunity to get into the lake and swim if you’d like!

  5. AI

    Alissa

    50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo

    Chartering through Michael and his team was the best decision we made in planning this boat ride. From the customer service and communication response time in booking to the captain’s knowledge and ensuring our safety, everything was amazing. This was a first for many of us but the boat had everything we needed, was perfect in size and Michael and Captain G made sure we were informed, prepared, and enjoyed ourselves! Thank you Michael and team again for an amazing time!! We’re already planning our next booking with you!

  6. CU

    Chinazor

    50' Sea Ray Sundancer Motor Yacht for 13 Guests in Chicago, IL -July Promo

    I booked this yacht for my birthday, and it was nothing short of amazing! Their hospitality is top-notch. Look no further!! The yacht comfortably fit my group of 9 (could take more as permitted)— very spacious! I loved every bit of my experience on Meridian. Will book again.