Top Chicago Sailing Tours

Admire a side of Chicago that few other visitors get to experience—and enjoy a relaxing trip out on the water, tailored to your party—with this private sailboat charter and sailing tour. You and up to five other guests will have the exclusive use of a sailboat, complete with a captain for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you can even take a turn at the helm.

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the boat rental for you! Amenities on board include: Pricing for private groups up to 7 guests. Custom pricing available for larger groups up to 12. Anchoring in the Chicago Playpen for swim and float parties. Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties. Large open cockpit seating area. Complimentary beverages and snacks or BYO (alcohol allowed). Stereo surround sound speakers with Bluetooth connection. Fridge with ice, fully stocked kitchenware. Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse. Anchoring for concerts at Northerly Island. Kitchen, bathroom and changing room on board.

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

See Chicago’s legendary Air & Water Show from the best seat in the city! Secure a VIP spot on a Lake Michigan cruise (or Skydeck viewing party) and watch the U.S. Air Force Thunderbirds, Golden Knights, and dazzling stunt pilots soar overhead. Enjoy premium amenities, from fast-track boarding to reserved seating, up-close views, and included food or drinks (per package). With unmatched photo ops and the sound of jets flying overhead, this is a must-see experience for locals and visitors alike—just in time for summer’s biggest Chicago festival. Book early; these shows always sell out fast.

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

Set sail on a private fireworks cruise along the Chicago Lakefront aboard a meticulously maintained sailing yacht. Enjoy complimentary drinks or BYO. Perfect for summer birthdays, romantic proposals, anniversaries, and any reason to celebrate Summertime Chi!