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All listings in Chicago

Search yacht rentals in Chicago, Illinois.

4.9

(4,322 Reviews)

Page 1 of 10 • 231 listings

Limited Availability

Events in Chicago · 6 guests

29ft Sea Ray Sundancer Captained Boat In Chicago

5.0

Superowner

$200/hour

Powerboats in Chicago · 13 guests

Rent this 42ft Regal Commodore Express Cruiser In Chicago

5.0

Superowner

Best of 2026

$225+/hour

Powerboats in Chicago · 13 guests

Maxum 44ft Motor Yacht "My Kinda Party"

4.9

Superowner

Best of 2026

$260+/hour

Events in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht

5.0

Superowner

Best of 2026

$300+/hour

Events in Chicago · 12 guests

40ft Formula 370 Sun Sport Motor Yacht Charter Chicago Playpen Ready

5.0

$300/hour

Events in Chicago · 12 guests

Affordable Private Boat Rental for 12 on Lake Michigan/Playpen-39' Sea Ray Yacht

5.0

$300/hour

Limited Availability

Events in Chicago · 12 guests

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

4.7

$400/hour

Limited Availability

Events in Chicago · 13 guests

'Genius' 40ft Sea Ray Sundancer Captained Charter With All Amenities In Chicago!

5.0

Superowner

$275/hour

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

Limited Availability

Events in Chicago · 12 guests

42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

5.0

$250/hour

Events in Chicago · 12 guests

42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!

5.0

$350/hour

Events in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests

5.0

Superowner

Best of 2026

$300+/hour

Limited Availability

Events in Chicago · 7 guests

35' Maxum Motor Yacht At Burnham Harbor, Captain/Fuel Included

5.0

$275/hour

High Demand

Events in Chicago · 6 guests

27ft Chris Craft Motor Yacht With Water Toys plus Jet Ski Available in Chicago!

4.9

Superowner

$250/hour

Limited Availability

Powerboats in Chicago · 12 guests

Relax and Enjoy Aboard this 51' Sea Ray Sundancer Yacht at Diversey Harbor

5.0

Superowner

Best of 2026

$255/hour

Limited Availability

Events in Chicago · 12 guests

37' Silverton Spacious Party Yacht For Every Occasion In Chicago

5.0

$225/hour

Powerboats in Chicago · 13 guests

Set Sail on a Spacious 42' Silverton Express Cruiser Yacht

5.0

$275/hour

Limited Availability

Events in Chicago · 13 guests

'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

5.0

Superowner

$350/hour

Limited Availability

Powerboats in Chicago · 8 guests

Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

4.6

$275/hour

Events in Chicago · 13 guests

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

4.8

$300/hour

Limited Availability

Events in Chicago · 12 guests

SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests

5.0

$200/hour

Events in Chicago · 8 guests

Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

4.7

$300/hour

Events in Chicago · 6 guests

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

5.0

$375/hour

Limited Availability

Events in Chicago · 6 guests

New 48ft Sport Coupe Yacht in Chicago River & Lake Charter

4.9

$300/hour

Top Destinations Nearby

Motor Yacht Reviews in Chicago

Cindy

Maxum 44ft Motor Yacht "My Kinda Party"
Had an amazing birthday weekend with my friends for my birthday, Captin Drake was great and I would definitely book again! Thank you for an amazing experience.
DC
Douglas

Double Decker 50ft Sea Ray Flybridge Yacht
Had a great time on the Chicago River and lake! Boat is a great value and lots of space to relax and enjoy the views.
KD
Kareem

2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois
Nilufar made the booking process so easy and we had no issues from start to finish!
Gia

Book "After Hours" today! Sea Ray Sundancer 40ft Motor Yacht In Chicago
Amazing boat, we had the best time.
Anameti

29ft Sea Ray Sundancer Captained Boat In Chicago
We had a great time out with Captain Memo! He was very friendly and warm. We went out for a birthday. It was too chilly to get in the water but we were so comfortable on the boat enjoying the sun. When we’re back in town we’d love to go out on the water again with Captain Memo!
GF
Grace

29ft Sea Ray Sundancer Captained Boat In Chicago
Just like the namesake of the boat, our experience with Captain Memo was truly Unforgettable. If you are looking to create life long memories with friends, this is the boat for you. Captain Memo was generous and kind and the boat had such a homey vibe. The experience made me feel like I was in a movie, and I recommend this trip to anyone who is looking for a little magic in their lives.