Bookings Now Open Summer 2025

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The professional and private yacht charter platform​


A Chicago Harbor yacht cruise is perfect for corporate events, a birthday party, wedding cruise, bar mitzvah, rehearsal dinner, anniversary, or any nautical celebration. We pride ourselves in the integrity of the advice we offer to each of our clients.

We provide competitive rates and exceptional customer service with our captains, who have more than 30 years of combined experience sailing coastal waters. Our yachts, fully certified by the U.S. Coast Guard, offer a unique and memorable setting for corporate events.
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  • 01
    An Evening Cruise Beneath Chicago's Dazzling Experience the magic of Chicago’s skyline illuminated by a spectacular twice-a-week fireworks show as you cruise Lake Michigan in style.
  • 02
    A Sun-Filled Rendezvous at the Lively Chicago Scene Soak up the sun and enjoy vibrant energy as you sail through Chicago’s bustling lakefront hotspots.
  • 03
    A Scenic Pass Around McCormick Place, Adler Planetarium, and Buckingham Fountain Take in breathtaking views of Chicago’s iconic landmarks from the serene waters of Lake Michigan.
  • 04
    Rent the Yacht and Chart Your Own Itinerary Create your dream voyage with a personalized route, available for a modest additional cost.
luxury & premium

Why choose us​

Fun in the Sun is a Chicago boat rental company that specializes in providing luxurious, yet affordable, yacht rentals on Lake Michigan.

more than

30 years
of experience navigating coastal waters

more than

20 years
of hospitality experience

more than

15 years
of boating experience

our story​

The story of FunSun

Fun in the Sun is a Chicago boat rental company that specializes in providing luxurious, yet affordable, yacht rentals on Lake Michigan. Our team offers more than 15 years of boating experience and 20 years of hospitality experience, providing the best boat rental experience. We are committed to guest education and safety in order to deliver our clients a full-service yacht rental that is both fun and safe.

our

Cancellation Policy

We accept all cancellations made 5 days or more prior to your charter date without any fees. Cancellations made within 5 days of the charter date are subject to a 100% cancellation fee.

All requests for cancellation and charges must be made emailed to us via the inquire tab.

As for weather, that is decided on the day of since Chicago weather changes fequently. In the case that conditions are deemed  “too dangerous”  our team will work with charterer to temporarily postpone or reschedule your charter to a future date.

what our clients say​
“Our trip was amazing from start to finish! The boat is awesome, it got everything we need, we snorkelled, used the paddle boards and enjoyed the breath taking view while sailing on this paradise island.”
Katy
Nov 2022, Charter sailboat
“My experience with Floaty was amazing from the first contact to the very end of the yacht trip. They were so professional and responsive through the booking process and made everything easy.”
Lapina
Nov 2022, Charter sailboat
“Our trip was amazing from start to finish! The boat is awesome, it got everything we need, we snorkelled, used the paddle boards and enjoyed the breath taking view while sailing on this paradise island.”
Yeheskel S
Nov 2022, Charter sailboat
“My experience with Floaty was amazing from the first contact to the very end of the yacht trip. They were so professional and responsive through the booking process and made everything easy.”
Ruth V.
Nov 2022, Charter sailboat
our team

Meet the crew

Connor Fox
captain
Connor Fox
captain
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Robert Garrett
receptionist
Robert Garrett
receptionist
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Jeny Mike
skipper
Jeny Mike
skipper
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John Smith
skipper
John Smith
skipper
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