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Boat Rentals & Yacht Charters Near You

4.9
(58,394 Reviews)

Page 4 of 10 • 240 listings

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
Spacious 50’  Yacht with Swim platform @ 31st Harbor
Events in Chicago · 12 guests

Spacious 50’ Yacht with Swim platform @ 31st Harbor

5.0
$400+/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
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
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
Sailing in Chicago · 6 guests

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

5.0
Snoozed - Active 14 Jun 2027
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
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
 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
New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago
Events in Chicago · 12 guests

New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago

5.0
Superowner
$400/hour
Come enjoy fun in the sun on our 30ft Bayliner Ciera (Captain fee not included)
Events in Chicago · 8 guests

Come enjoy fun in the sun on our 30ft Bayliner Ciera (Captain fee not included)

4.8
$200/hour
Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht
Events in Chicago · 10 guests

Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht

5.0
$275/hour
Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!
Events in Chicago · 12 guests

Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!

5.0
Superowner
$300+/hour
Big Space. Big Fun. Easy on Your Budget
Events in Chicago · 12 guests

Big Space. Big Fun. Easy on Your Budget

5.0
$250/hour
Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!
Events in Chicago · 12 guests

Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!

4.9
$300/hour
Luxury 54' Sea Ray Sundancer Yacht for Charter in Chicago
Events in Chicago · 12 guests

Luxury 54' Sea Ray Sundancer Yacht for Charter in Chicago

4.2
$500/hour
Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht
Powerboats in Chicago · 12 guests

Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht

4.7
Superowner
$350/hour

Local 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. TF

    Todd

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

  4. TZ

    Ty

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

    Our group of 12 people had an awesome time on the boat. Coordination and communication was great throughout and we had a perfect day on the lake with Captain Mike. I would absolutely charter from Tristan again.

  5. QT

    QUAN

    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

    DO IT! Highly recommend! Captain Kyle responds quickly and is super accommodating. Our group had a fantastic time and would do again in a heartbeat.

  6. Osamudiamien

    Osamudiamien

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

    Had one of the best times I’ve ever had with my closest group of friends. The boat was a beautiful piece of architecture, the captain was very nice, and being in the playpen for a few hours is something special. Can’t wait to book another boat with Tristian in the near future. My only advice to people is that if you’re considering doing this, don’t wait. Book it now.