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Boat Rentals & Yacht Charters Near You

4.9
(58,394 Reviews)

Page 3 of 10 • 240 listings

21' Lund Walleye Boat for 3 in Chicago, Illinois
Fishing in Chicago · 3 guests

21' Lund Walleye Boat for 3 in Chicago, Illinois

5.0
$75/hour
Professionally Maintained 50' Sea Ray Sundancer  for 12 Passengers in Chicago
Events in Chicago · 12 guests

Professionally Maintained 50' Sea Ray Sundancer for 12 Passengers in Chicago

4.9
$350/hour
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 13 guests

41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
Best of 2026
$275+/hour
Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
Events in Chicago · 12 guests

Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience

5.0
$350/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
55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand
Events in Chicago · 12 guests

55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

5.0
Snoozed - Active 02 Jan 2027
'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!
Events in Chicago · 13 guests

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

5.0
Superowner
$350/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
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
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
Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht
Events in Chicago · 12 guests

Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht

5.0
Superowner
Best of 2026
$450/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
39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

39' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
Best of 2026
$250+/hour
42' Mediterranean Yacht for Luxury Cruises in Chicago - 3 Boats Available!
Events in Chicago · 12 guests

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

5.0
$400/hour
Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!
Powerboats in Chicago · 9 guests

Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!

5.0
$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
44' Luxury Sundancer Yacht in Chicago Includes Captain and Floating Island!
Events in Chicago · 12 guests

44' Luxury Sundancer Yacht in Chicago Includes Captain and Floating Island!

4.8
$349/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
Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago
Events in Chicago · 13 guests

Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago

5.0
Superowner
Best of 2026
$275+/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
Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests
Powerboats in Chicago · 13 guests

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

5.0
Superowner
Best of 2026
$300+/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

Local Reviews

  1. brett

    brett

    Luxury Boating Experience in Chicago aboard Sea Ray 550 Sedan Bridge Yacht

    Best day ever. Boat was better than advertised, even more spacious than we realized and very well kept. Eric and Claudia were our captain and crew and they made the day even better. Very friendly and accommodating. Our group of 12 had the best day. Highly recommend 10/10

  2. AC

    Amber

    Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago

    We had an amazing experience chartering Captain James' boat ICEMAN IV for our team of nurses! Captain K was outstanding, professional, friendly, fun, and made sure everyone had a great time. The entire experience was seamless from start to finish, and our group truly had the best time. We couldn’t have asked for a better captain or experience. Highly recommend!

  3. KR

    Kyler

    Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago

    Captain James and his wife run a fantastic operation. The boat was in pristine condition and ready exactly when they said it would be. Our captain (captain aaron) was great and even volunteered to get a group photo before we departed. I highly recommend this boat and will book with them again for future excursions

  4. CM

    Carolyn

    Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!

    Our experience with Frank was stellar from start to finish. He was a great communicator - informed, friendly, prompt, and willing to work with us on special requests. The boat was pristine and perfect for the occasion. Great sound system, storage, and seating areas, and it's a huge plus to have a bathroom on a boat that size. We did an evening cocktail cruise, but it would be fantastic for a daytime outing too. Highly recommend!

  5. KY

    Katherine

    Captained 41' Sea Ray Sundancer Motor Yacht for Charter in Chicago

    Captain James and family make this boating experience so easy and enjoyable. I will definitely ride with them again! The boat is so clean and accommodates 12 people comfortably. I highly recommend!

  6. Sigourney

    Sigourney

    Maxum 44ft Motor Yacht "My Kinda Party"

    Chris was wonderful to work with, super helpful and responsive. We had such a great time! Thank you for everything!