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Chicago, Illinois Boat Rentals & Yacht Charters

Page 4 of 12 • 281 listings

37' Silverton Spacious Party Yacht For Every Occasion In Chicago
Events in Chicago · 12 guests

37' Silverton Spacious Party Yacht For Every Occasion In Chicago

4.9
$225/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
35' Luxury Motor Yacht Charter in Chicago with Swim Platform
Events in Chicago · 12 guests

35' Luxury Motor Yacht Charter in Chicago with Swim Platform

4.2
$180+/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
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
Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
Sailing in Chicago · 10 guests

Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

5.0
Superowner
$250/hour
40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests
Events in Chicago · 12 guests

40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests

4.9
$300/hour
Private Charter 38' Party Pontoon for up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

Private Charter 38' Party Pontoon for up to 20 Guests in Chicago

5.0
Superowner
Best of 2026
$700/hour
Luxury Multi Level 38ft Meridian Yacht! Water Toys Included - Chicago, IL (I)
Events in Chicago · 13 guests

Luxury Multi Level 38ft Meridian Yacht! Water Toys Included - Chicago, IL (I)

5.0
Superowner
$250/hour
Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties
Events in Chicago · 12 guests

Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

5.0
Superowner
Best of 2026
$400/hour
Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago
Events in Chicago · 13 guests

Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago

4.9
$400/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
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
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Powerboats in Chicago · 5 guests

Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

5.0
Superowner
$225/hour
38' Four Winns 378 Vista Motor Yacht in Chicago, Illinois
Events in Chicago · 12 guests

38' Four Winns 378 Vista Motor Yacht in Chicago, Illinois

4.8
$408/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
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Ready to Use Doral Alegria 50' Yacht in Chicago, Illinois
Events in Chicago · 12 guests

Ready to Use Doral Alegria 50' Yacht in Chicago, Illinois

5.0
$225/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
62ft Azimut Italian Yacht Charter Chicago for Up to 12 Guests
Events in Chicago · 12 guests

62ft Azimut Italian Yacht Charter Chicago for Up to 12 Guests

5.0
Superowner
Best of 2026
$1,000/hour
Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests
Events in Chicago · 12 guests

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

3.9
$250/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
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
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

Chicago Reviews

  1. CU

    Chinazor

    Elegant 46ft Prestige Flybridge Luxury Yacht In Chicago

    Awesome experience! I booked this vessel on July 3rd to take birthday photos with a few friends. It’s spacious! Although it mostly rained, Captain Craig was incredible— very professional, great with the boat, and excellent with communication throughout the experience. I definitely will be booking again ✨

  2. LT

    Lauren

    40' Luxury Cruiser Yacht for Charter in Chicago - Accommodate up to 12 guests

    Our group had an amazing time! Was easy to book and had quick responses from Captain G. We loved the boat and our driver TJ! She was so fun, we’ll definitely be requesting her next time. They sent photos of our trip right after, can’t wait to book again.

  3. 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.

  4. MM

    Melanie

    Luxury Multi Level 38ft Meridian Yacht! Water Toys Included - Chicago, IL (I)

    My friends and I had a blast with Captain Derek and his first mate! They did everything they could to ensure a safe trip while going above a beyond to make it a fun time. Such a great experience and would highly recommend for your next outing!

  5. Pradyu

    Pradyu

    37' Silverton Spacious Party Yacht For Every Occasion In Chicago

    Had a fantastic time on the yacht! Communication and service were excellent throughout, and the captain made everything smooth. The boat was a little rocky, but I’d chalk that up to the conditions of the day. Overall, an amazing day out on the water — would definitely recommend

  6. CC

    Carlos

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

    Captain J is awesome! He is very responsive and answered any and all questions I had prior to the trip. His boat is great and very well maintained. It is also very spacious. We had a party of 11 and we felt like we had plenty of room on the boat. We will definitely be returning in the future!