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    All listings in Chicago

    Boat tours in Chicago, Illinois.

    4.9
    (5,425 Reviews)

    Page 2 of 11 • 254 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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

    5.0
    $225/hour
    Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago
    Powerboats in Chicago · 6 guests

    Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

    5.0
    $225/hour
    Limited Availability
    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina
    Events in Chicago · 13 guests

    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

    5.0
    $300/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
    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
    $300/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
    $300/hour
    High Demand
    62ft Azimut Italian Yacht Charter Chicago for Up to 6 Guests
    Events in Chicago · 6 guests

    62ft Azimut Italian Yacht Charter Chicago for Up to 6 Guests

    5.0
    Superowner
    Best of 2026
    $500/hour
    High Demand
    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
    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
    High Demand
    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
    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
    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
    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
    27ft Sea Ray Sundancer Cruiser on Lake Michigan near Chicago for Up to 8 Guests
    Events in Chicago · 8 guests

    27ft Sea Ray Sundancer Cruiser on Lake Michigan near Chicago for Up to 8 Guests

    5.0
    $160/hour
    High Demand
    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
    High Demand
    Chicago 40ft Formula Performance Cruiser for Up to 13 Guests
    Events in Chicago · 13 guests

    Chicago 40ft Formula Performance Cruiser for Up to 13 Guests

    5.0
    $349/hour
    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
    High Demand
    Luxury Chaparral 277 SSX Wakeboat for 10 Guests In Chicago
    Powerboats in Chicago · 10 guests

    Luxury Chaparral 277 SSX Wakeboat for 10 Guests In Chicago

    5.0
    $175/hour
    Limited Availability
    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
    High Demand
    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
    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
    46ft Maxum Motor Yacht Charters at Belmont Harbor Chicago Lake Michigan
    Events in Chicago · 6 guests

    46ft Maxum Motor Yacht Charters at Belmont Harbor Chicago Lake Michigan

    5.0
    $400/hour
    Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev
    Events in Chicago · 13 guests

    Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

    5.0
    Superowner
    Best of 2026
    $500/hour
    Instant Book

    Top Destinations Nearby

    Tours Reviews in Chicago

    1. LW

      Leteshia

      Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

      WOW! My birthday boating experience couldn’t have been any greater! Starting with him showing up on time and already having everything ready to go for us and everything was soo nice and clean ! The speaker system was amazing, he was very Courteous and had real genuine good vibes! The scenery was EVERYTHING! I would highly recommend booking him ! He even captured some pictures and videos of us and everything turned out PERFECT! Thanks Samuel my birthday has been made 🙂 DEFINITELY BOOK HIM!

    2. JN

      Jessica

      Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

      Such a lovely trip. Up to the trip Kevin and his team were extremely responsive. This was amazing and we will be doing this again! Thanks!

    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. CF

      Connie

      45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

      Look no further for your boat rental needs. Captain Douglas will help you choose the perfect boat and crew to make your experience beyond what you can imagine!!

    5. JD

      Jorge

      Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

      Great service, great vibes, chill, definitely recommend and will take another ride again!

    6. AW

      Ashley

      Chicago Lake Michigan Yacht Charter aboard 43' Sea Ray Sundancer w/ Captain Kev

      Very responsive and helpful. Great experience!

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