ON A BOAT SAILING

CHICAGO CRUISES & CHARTERS

SERVICES

2023 SAILBOAT RENTAL BOOKINGS NOW OPEN

SAIL & SWIM

SKYLINE CRUISE

FIREWORKS CRUISE

CUSTOM CHARTER*

Summer at its finest in Chicago! Chill in the Lake with a floatie, practice diving, lounge on the deck with your favorite drink at the Playpen

Your favorite people, tunes, drinks & snacks! Ride the wind with un-comparable views of the Chicago skyline and Lake Michigan

Get the best possible seats for the Navy Pier Fireworks! Every Wednesday and Saturday night, Memorial Day to Labor Day

Something else in mind? Private lessons, Photoshoots, engagements, bachelorette parties! Up to ten guests for custom pricing inquire

BOOK NOW

On A Boat Sailing is Chicago's top rated sailing experience and private sailing charter offering a variety of boat rides, sailing charters, sightseeing tours, playpen float parties, and customized private cruises on Lake Michigan. Our focus is on curated experiences for small groups looking for fun and celebration, romance, photography, relaxation or just good times. No matter the occasion, we will set the vibe right for you!

We sail seven days a week during our season of mid May to mid October with multiple departures each day. Explore our website and checkout all of the sailing cruises we have for you this season, or please get in touch with your ideas. We have hosted proposals, photoshoots, bachelorette parties, birthdays, anniversaries and corporate lunch outings.

We love sharing our passion for sailing with travelers and locals of all ages. For us, sailing offers adventure, relaxation, and the discovery of new places and like minded friends. Chicago is the best place to combine the thrill of sailing with views of a world class skyline-let us show you.

Cheers!

Greg and Cait