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    Illinois, US Boat Rentals & Yacht Charters

    4.9
    (5,756 Reviews)

    Page 2 of 13 • 302 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Limited Availability
    '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
    20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!
    Powerboats in Chicago · 20 guests

    20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

    5.0
    Superowner
    Best of 2026
    $700/hour
    Limited Availability
    Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois
    Powerboats in Chicago · 8 guests

    Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

    4.6
    $275/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
    Limited Availability
    SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests
    Events in Chicago · 12 guests

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

    5.0
    $200/hour
    Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago
    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
    Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht
    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
    New 48ft Sport Coupe Yacht in Chicago River & Lake Charter
    Events in Chicago · 6 guests

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

    4.9
    $300/hour
    44ft Regal Luxury Yacht Perfect for Playpen Parties and Lake Michigan Cruises!
    Events in Chicago · 12 guests

    44ft Regal Luxury Yacht Perfect for Playpen Parties and Lake Michigan Cruises!

    5.0
    $275+/hour
    Limited Availability
    Cruisers Y3375 Express Yacht Downtown Chicago Experience
    Powerboats in Chicago · 10 guests

    Cruisers Y3375 Express Yacht Downtown Chicago Experience

    5.0
    Superowner
    $250/hour
    Limited Availability
    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!
    Events in Chicago · 12 guests

    Explore the Famous Chicago Playpen! - 46ft Sea Ray Motor Yacht!

    5.0
    Superowner
    Best of 2026
    $220/hour
    Instant Book
    Limited Availability
    37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen
    Events in Chicago · 12 guests

    37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen

    5.0
    Superowner
    Best of 2026
    $220/hour
    Instant Book
    Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests
    Events in Chicago · 7 guests

    Captained 51' Sea Ray Sundancer Luxury Yacht in Chicago - 7 Guests

    5.0
    Superowner
    $500+/hour
    Limited Availability
    Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht
    Events in Chicago · 12 guests

    Anchor in the Famous Chicago Playpen with 37' Rinker Fiesta Vee Yacht

    5.0
    Superowner
    Best of 2026
    $325/hour
    Instant Book
    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago
    Events in Chicago · 13 guests

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

    5.0
    $275/hour
    27ft Sea Ray Deck Boat for 5 Guests, Captain Included
    Powerboats in Chicago · 5 guests

    27ft Sea Ray Deck Boat for 5 Guests, Captain Included

    5.0
    $235/hour
    Limited Availability
    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests
    Sailing in Chicago · 6 guests

    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

    5.0
    $225/hour
    33ft Bayliner Powerboat Charter in Chicago for 10 Guests
    Events in Chicago · 10 guests

    33ft Bayliner Powerboat Charter in Chicago for 10 Guests

    4.6
    $300/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
    $275/hour
    Limited Availability
    Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties
    Events in Chicago · 12 guests

    Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties

    5.0
    Superowner
    Best of 2026
    $400/hour
    Instant Book
    Limited Availability
    44ft Azimut Premier Party Yacht Chicago for Up to 13 - plus Jet Ski Available
    Events in Chicago · 13 guests

    44ft Azimut Premier Party Yacht Chicago for Up to 13 - plus Jet Ski Available

    5.0
    Superowner
    $625+/hour
    Limited Availability
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
    Sailing in Chicago · 6 guests

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    5.0
    Superowner
    Best of 2026
    $220/hour
    Limited Availability
    46' Sunseeker Portofino Yacht in Chicago for Parties & Events
    Events in Chicago · 12 guests

    46' Sunseeker Portofino Yacht in Chicago for Parties & Events

    4.7
    $250/hour
    Limited Availability
    Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper
    Events in Chicago · 12 guests

    Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper

    4.7
    $250+/hour

    Top Destinations Nearby

    Illinois Reviews

    1. WK

      William

      Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

      Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!

    2. KS

      Kailey

      20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

      We booked with Troy for an outing of 20 people and everyone had such a great time! Communication was very easy prior to the trip, having a captain included was huge, they have tables set up for games and food, a speaker system, floaties for the water, and the crew was very helpful! The views were also amazing! Would definitely recommend and would do again

    3. Reanna

      Reanna

      Cruisers Y3375 Express Yacht Downtown Chicago Experience

      The boat day was our favorite part of our bachelorette trip. We had the best time and we loved Captain Sam! 10/10 recommend this company!

    4. LO

      Leila

      37ft Beautiful Sea Ray Venture Motor Yacht - Explore Chicago's Famous Playpen

      The rental was a smooth process, answered all questions very quickly. The boat was clean and captain Mike was great!!

    5. SB

      Shannon

      20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

      We had so much fun with Captain Jerry and Steve! We rented the boat for a bachelorette and the boat was perfect for moving around and hanging out. It was raining a bit and we were able to be under cover for that time. Steve and Jerry were so attentive and wonderful to ride with. I will definitely be looking to rent with them again!

    6. EB

      Emmie

      20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

      10/10!!!!Captain Troy was amazing from the start. He communicated so well and had so much energy and excitement about us booking. Day of our captain’s Jerry and Steve were amazing!!!! They were so kind and helpful from start to Beginning. We had such an amazing time!! 5 stars all the way book these guys!!!😁😁

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