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Boat Rentals & Yacht Charters Near You

4.9
(67,463 Reviews)

Page 8 of 10 • 240 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
41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago
Events in Chicago · 13 guests

41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago

5.0
Superowner
Best of 2026
$275+/hour
Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht
Events in Chicago · 12 guests

Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht

5.0
Superowner
Best of 2026
$250+/hour
August & September Specials:  Private Boat Rental for Up to 12
Events in Chicago · 12 guests

August & September Specials: Private Boat Rental for Up to 12

5.0
$250/hour
44ft Chris-Craft 412 Amerosport Party Yacht in Chicago Harbor
Events in Chicago · 13 guests

44ft Chris-Craft 412 Amerosport Party Yacht in Chicago Harbor

New
$295/hour
Chicago looks better from the deck of 45' Rinker Motor Yacht
Events in Chicago · 12 guests

Chicago looks better from the deck of 45' Rinker Motor Yacht

5.0
$350/hour
Private Boat Charter - Sea Ray 390 Sundancer In Chicago
Events in Chicago · 12 guests

Private Boat Charter - Sea Ray 390 Sundancer In Chicago

5.0
$200/hour
Party Cruise on 40ft Sea Ray Express Yacht Chicago for You & 12 Friends
Events in Chicago · 12 guests

Party Cruise on 40ft Sea Ray Express Yacht Chicago for You & 12 Friends

5.0
$300+/hour
Unique Experience with our Sea Ray 330 Sundancer Yacht for 7 Guests in Chicago
Powerboats in Chicago · 7 guests

Unique Experience with our Sea Ray 330 Sundancer Yacht for 7 Guests in Chicago

5.0
Snoozed - Active 02 Jan 2027
2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois
Events in Chicago · 12 guests

2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

4.7
$400/hour
Cruisers Y3375 Express Yacht Downtown Chicago Experience
Powerboats in Chicago · 10 guests

Cruisers Y3375 Express Yacht Downtown Chicago Experience

5.0
Superowner
$250/hour
Cruise Lake Michigan on a 39ft Sea Ray 390 Express Cruiser for 12 Guests
Events in Chicago · 12 guests

Cruise Lake Michigan on a 39ft Sea Ray 390 Express Cruiser for 12 Guests

5.0
$250/hour
Take in Breathtaking Chicago Skyline Views from Spacious 32' Chaparral Yacht
Events in Chicago · 12 guests

Take in Breathtaking Chicago Skyline Views from Spacious 32' Chaparral Yacht

New
$450/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
Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago
Events in Chicago · 12 guests

Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago

4.9
$350/hour
Luxury 39’ Sea Ray Sport Cruiser in Chicago, Illinois
Events in Chicago · 12 guests

Luxury 39’ Sea Ray Sport Cruiser in Chicago, Illinois

5.0
$225/hour
Private Luxury Charter In Chicago - Sea Ray 360 Sundancer Motor Yacht
Events in Chicago · 13 guests

Private Luxury Charter In Chicago - Sea Ray 360 Sundancer Motor Yacht

5.0
$300/hour
40ft Carver Mariner Motor Yacht Charter in Chicago
Events in Chicago · 13 guests

40ft Carver Mariner Motor Yacht Charter in Chicago

New
$745/hour
Exquisite Mediterranean 40' with Flybridge Yacht in Chicago
Events in Chicago · 12 guests

Exquisite Mediterranean 40' with Flybridge Yacht in Chicago

5.0
$400/hour
39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included
Events in Chicago · 12 guests

39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included

5.0
$350+/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
32' Maxum 3000 SCR Motor Yacht on Lake Michigan - Chicago
Events in Chicago · 10 guests

32' Maxum 3000 SCR Motor Yacht on Lake Michigan - Chicago

5.0
$300/hour
Captained Charter on 36' Sea Ray Cruiser in Chicago
Events in Chicago · 12 guests

Captained Charter on 36' Sea Ray Cruiser in Chicago

4.8
$350/hour
Beautiful 39ft Double Decker Carver Mariner Luxury Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Beautiful 39ft Double Decker Carver Mariner Luxury Yacht in Chicago, Illinois

New
$350/hour

Local Reviews

  1. CS

    Crystal

    Cruisers Y3375 Express Yacht Downtown Chicago Experience

    Me and my friends had a great boat ride! Ramsey was extremely easy to communicate with and was very responsive throughout the entire process. He even FaceTimed us to walk us through how to setup the Bluetooth because we weren’t able to get it to work while on the boat. I would definitely recommend this boat charter and Captain Sam for your operator!

  2. Kathy

    Kathy

    39' Sea Ray Express Cruiser for Rent in Chicago with Captain Included

    George and his boat crew were absolutely amazing! We had such a fun time out on the boat and couldn’t have asked for a better experience. Everyone was friendly, welcoming, and made sure our group was comfortable and having a great time from start to finish. The whole experience was easy, fun, and memorable. We’ll definitely be booking with George and his crew again and would highly recommend them to anyone looking for an amazing day out on the water!

  3. 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!

  4. SD

    Sam

    Chicago looks better from the deck of 45' Rinker Motor Yacht

    Gill and Captain Maurice made chartering a boat so easy and stress free and were so accommodative. They worked with us to find a better departure time when the morning weather was a bit iffy and overall made the whole charter so smooth and fun! Highly recommend!!

  5. 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!

  6. HB

    Haniyyah

    Cruise Lake Michigan in Chicago aboard 39' Sea Ray Sundancer Motor Yacht

    Thank you for an amazing experience! My friends and I had a fantastic time on Lake Michigan. The boat was clean and well-maintained, the sound system was great, and our captain was professional, friendly, and made sure we had an incredible time. Everything on the water exceeded our expectations.