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Find Tours on the Water Near You

4.9
(27,138 Reviews)

Page 3 of 10 • 240 listings

Chicago’s Casual Lakefront Escape On 29' Sea Ray Sundancer Yacht - 12 Guests
Events in Chicago · 12 guests

Chicago’s Casual Lakefront Escape On 29' Sea Ray Sundancer Yacht - 12 Guests

New
$250/hour
44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain
Events in Chicago · 13 guests

44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain

4.8
$349/hour
Double Decker 50ft Sea Ray Flybridge Yacht
Events in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht

5.0
Superowner
Best of 2026
$300+/hour
62' Azimut Italian Luxury Yacht for Rent  in Chicago, Illinois for 13 Guests
Events in Chicago · 13 guests

62' Azimut Italian Luxury Yacht for Rent in Chicago, Illinois for 13 Guests

3.0
$1,000/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
100ft Denison Party Yacht with Jacuzzi and Bar at 31st Harbor, Chicago
Events in Chicago · 30 guests

100ft Denison Party Yacht with Jacuzzi and Bar at 31st Harbor, Chicago

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

Set Sail on a Spacious 42' Silverton Express Cruiser Yacht

5.0
$275/hour
Rent this 42ft  Regal Commodore Express Cruiser In Chicago
Powerboats in Chicago · 13 guests

Rent this 42ft Regal Commodore Express Cruiser In Chicago

5.0
Superowner
Best of 2026
$225+/hour
Maxum 44ft Motor Yacht "My Kinda Party"
Powerboats in Chicago · 13 guests

Maxum 44ft Motor Yacht "My Kinda Party"

5.0
Superowner
Best of 2026
$260+/hour
Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago
Events in Chicago · 13 guests

Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago

4.8
$300/hour
Multi Level 48' Carver Mariner Yacht for 13 Guests in Chicago, IL
Events in Chicago · 13 guests

Multi Level 48' Carver Mariner Yacht for 13 Guests in Chicago, IL

5.0
$350/hour
Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago
Events in Chicago · 12 guests

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

5.0
$275/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
Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago
Events in Chicago · 13 guests

Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago

5.0
Superowner
Best of 2026
$225+/hour
44ft Regal Commodore Motor Yacht Charter In Chicago
Events in Chicago · 13 guests

44ft Regal Commodore Motor Yacht Charter In Chicago

5.0
$275/hour
38ft 'The Gwen' Carver Mariner Captained Charter With All Amenities In Chicago!
Events in Chicago · 13 guests

38ft 'The Gwen' Carver Mariner Captained Charter With All Amenities In Chicago!

4.9
Superowner
$275/hour
Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!
Events in Chicago · 10 guests

Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!

5.0
$300+/hour
New Boat in Chicago! 55ft Sea Ray Sundancer, Sleek & Spacious
Events in Chicago · 13 guests

New Boat in Chicago! 55ft Sea Ray Sundancer, Sleek & Spacious

New
Superowner
Best of 2026
$450/hour
44' Luxury Sea Ray Express Yacht Rental/Party Boat with Captain in Chicago
Events in Chicago · 13 guests

44' Luxury Sea Ray Express Yacht Rental/Party Boat with Captain in Chicago

4.9
$349/hour
 50ft Double Deck Yacht "Liquid Asset 3" in Chicago!
Events in Chicago · 13 guests

50ft Double Deck Yacht "Liquid Asset 3" in Chicago!

5.0
Superowner
Best of 2026
$300/hour
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 2026
$150+/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
42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion
Events in Chicago · 12 guests

42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

5.0
$225/hour

Local Tours Reviews

  1. SS

    Sonja

    44ft Regal Commodore Motor Yacht Charter In Chicago

    Robert was awesome! Very communicative, great boat driver, flexible with scheduling changes, professional, and kept us safe! Great value for the experience, good sound system, fun time for my bachelorette, and very experienced! The more flexible refund policy due to weather conditions helped us pick him as well since we didn’t live there but we didn’t need to use it thankfully! Thanks so much for taking care of us. Would book with him again if we lived in chicago!

  2. IC

    Isabel

    Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago

    We absolutely loved our experience! Our captain, Drake, was wonderful and we were very impressed with the boat. We had 13 guests, and the boat was comfortable for all of us. We went on a Saturday evening and enjoyed the fireworks and city views. Highly recommend!

  3. Dorissa

    Dorissa

    44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain

    Our group had an amazing time! We truly had such a fun and memorable experience. Our captain was incredibly professional, communicative, and kind from start to finish. The entire booking process was excellent and communication was perfect. Everything exceeded our expectations....We are absolutely going to book again.

  4. Haylie

    Haylie

    44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain

    We rented a boat in Chicago yesterday for my sister’s bachelorette party, and overall had a great time! First off, Max was an amazing captain — very friendly, helpful, and professional. He made us feel comfortable and ensured we had a smooth ride. The boat itself was clean, spacious, and had a nice downstairs area with a bathroom. We loved being able to lounge on the Lilly pad raft and enjoy the sunshine on the lake! That said, we were disappointed by the lack of transparency with the charges. Before the trip, we were not informed that a 20% automatic tip ($400) would be added on top of the nearly $3,000 we paid, which already included a $300 “service charge.” We had assumed that service charge was the gratuity. We fully intended to tip Max ourselves after the trip, but instead felt blindsided by the pre-added gratuity. The communication from both Get My Boat and the boat company could have been much clearer, and we were never provided with a full contract to review ahead of time. While we had fun and appreciated Max’s service, the surprise charges left us feeling taken advantage of. Transparency is key, and I hope the company addresses this for future customers.

  5. Mariah

    Mariah

    44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain

    Jimmy’s boat was great and so was our captain! He was patient helped us out—the dock was towards the end of the harbor and he offered to drive closer to pick up so we wouldn’t need to walk so far with all our things! Thanks for a great experience!

  6. Anna

    Anna

    44' Sea Ray Express Luxury Motor Yacht in Chicago with USCG Captain

    Amazing time on the lake and at the playpen! Perfect day and our captain was great! Keep in mind you have to plan to walk from the drop off area at 31st street harbor entrance, or wherever you park, and have a safety discussion before you leave so if get there 30 minutes early to walk from your car to the gate and get on board and settled to leave at your designated time.