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    Find Tours on the Water Near You

    4.9
    (10,995 Reviews)

    Page 2 of 10 • 240 listings

    24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches
    Powerboats in Chicago · 5 guests

    24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches

    5.0
    $200/hour
    Chicago Luxury Boat Rental
    Events in Chicago · 10 guests

    Chicago Luxury Boat Rental

    5.0
    Snoozed - Active 20 Aug 2025
    Experience Lake Michigan like never before on Beautiful 35ft Maxum
    Events in Chicago · 10 guests

    Experience Lake Michigan like never before on Beautiful 35ft Maxum

    4.8
    $225/hour
    68' Luxurious Private Yacht Charters in Chicago
    Events in Chicago · 45 guests

    68' Luxurious Private Yacht Charters in Chicago

    5.0
    $1,750/hour
    Experience Lake Michigan like never before!!!!!
    Events in Chicago · 8 guests

    Experience Lake Michigan like never before!!!!!

    New
    $225/hour
    Willard Marine SeaForce!! Former Military Adventure Boat!
    Powerboats in Chicago · 6 guests

    Willard Marine SeaForce!! Former Military Adventure Boat!

    New
    $270/hour
    Burnham Harbor, CAPTAIN/FUEL INCLUDED
    Events in Chicago · 7 guests

    Burnham Harbor, CAPTAIN/FUEL INCLUDED

    5.0
    $250+/hour
    Beautiful 40ft Sea Ray Yacht
    Events in Chicago · 12 guests

    Beautiful 40ft Sea Ray Yacht

    New
    $250/hour
    Lakeside Paradise Escape with Premier 310 Escalante Double Decker Tritoon
    Powerboats in Dandridge · 12 guests

    Lakeside Paradise Escape with Premier 310 Escalante Double Decker Tritoon

    New
    $333/hour
    Instant Book
    Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
    Sailing in Chicago · 6 guests

    Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

    5.0
    $450/hour
    No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA
    Events in Chicago · 36 guests

    No tie ups - BIG BOAT for up to 36 people - at NAVY PIER MARINA

    5.0
    $793/hour
    Sail & Swim from a Luxury Sailing Yacht
    Sailing in Chicago · 7 guests

    Sail & Swim from a Luxury Sailing Yacht

    5.0
    Superowner
    $200/hour
    Instant Book
    Big Party Boat for up to 24 people - at Navy Pier Marina
    Events in Chicago · 24 guests

    Big Party Boat for up to 24 people - at Navy Pier Marina

    New
    Snoozed - Active 02 Sep 2025
    Sailing Lessons with Chicago's #1 Rated Sailing School
    Tours in Chicago · 6 guests

    Sailing Lessons with Chicago's #1 Rated Sailing School

    New
    Best of 2025
    $175+/hour
    Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay
    Events in Chicago · 12 guests

    Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay

    New
    $400/hour
    46' luxury yacht for up to 12 people - DUSABLE Harbor
    Events in Chicago · 12 guests

    46' luxury yacht for up to 12 people - DUSABLE Harbor

    New
    $280/hour
    No tie ups - 40ft Premium Yacht - lots of room group of for 12 - DuSable Harbor
    Events in Chicago · 12 guests

    No tie ups - 40ft Premium Yacht - lots of room group of for 12 - DuSable Harbor

    New
    $250/hour
    Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
    Events in Chicago · 12 guests

    Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

    4.9
    Superowner
    Best of 2025
    $200/hour
    DiverseyHarbor Luxury 44' Yacht- Free Champagne, Free Fuel, Free Floating Island
    Events in Chicago · 12 guests

    DiverseyHarbor Luxury 44' Yacht- Free Champagne, Free Fuel, Free Floating Island

    5.0
    $375/hour
    Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
    Powerboats in Chicago · 12 guests

    Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

    4.8
    Superowner
    Best of 2025
    $210/hour
    Luxury Sea Ray Sundancer for up to 12 peope
    Events in Chicago · 12 guests

    Luxury Sea Ray Sundancer for up to 12 peope

    4.0
    $400/hour
    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
    Powerboats in Chicago · 12 guests

    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

    5.0
    Superowner
    Best of 2025
    $170/hour
    26’ Sea Ray 240 Sundeck
    Powerboats in Chicago · 10 guests

    26’ Sea Ray 240 Sundeck

    1.0
    $225/hour
    Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.
    Powerboats in Chicago · 6 guests

    Cpt included. A perfect blend of comfort and adventure aboard Sea Ray Sundancer.

    5.0
    $225+/hour

    Local Tours Reviews

    1. CM

      Connor

      Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

      Fantastic day on the water! The entire process was so smooth and easy to get ready for the rental. Finding a captain was easy and Hayden was phenomenal! He was very clear with what we needed and safety in/around the boat. Will definitely be booking again in the future

    2. AE

      Alexandra

      24’ Robalo CC Lake Michigan charters. Downtown Chicago to the Indiana beaches

      Bill was the best charter I’ve used! So communicative, accommodating, and really made our trip to Chicago amazing. Made everything feel safe while also having a blast in the playpen. Can’t wait to come back to Chicago and book with him again!

    3. CS

      Carol

      Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

      We had such a great time! Our captain, Zack, was great and super friendly! Communication with the Captain and owner was super simple and always met with a quick response. Our group is already talking about the next time we can go out! Such a great find!

    4. MM

      Marina

      Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

      We had a blast sailing on Kevin’s boat. Everything was as described. Great communication and straightforward booking experience with the owner Kevin and captain Ron. Thank you for making our daughter’s birthday memorable and fun!

    5. SR

      Staci

      DiverseyHarbor Luxury 44' Yacht- Free Champagne, Free Fuel, Free Floating Island

      I would highly recommend booking with Nick. The boat was very nice, Nick was super responsive and easy to work with, and his Captain pick (Lee) was amazing. No complaints and made for a very smooth booking and charter experience.

    6. TK

      Taran

      Chicago Luxury Boat Rental

      My girls and I book this boat for a little day out, and it was more than perfect! Captain Jose and Captain Tony were so sweet and attentive and constantly communicated how the weather was looking and our plan. The boat was bigger than we thought and such a nice surprise. I could not recommend Captain Savage more!

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