Top Chicago Sailing

Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.

Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.

Get views of Chicago's famous architecture from the deck of a boat during this sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 

If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.

Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 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.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

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 in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Board a luxurious yacht at Navy Pier for a 2-hour lunch cruise along Chicago’s scenic shoreline. Enjoy a three-course gourmet meal as you take in views of the Windy City from a climate-controlled observation deck, then sip coffee or tea while the yacht’s onboard DJ spins a leisurely afternoon playlist.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Watch Navy Pier's fireworks display from the deck of a sailboat. During this 75-minute cruise on Lake Michigan, get views of the Chicago city skyline lit up at night and the colorful fireworks exploding over the lake. Listen to your guide's commentary about the city's history and join in on some traditional shipboard working songs if you like.

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.

See the sights of Chicago from the water during a 90-minute tall ship sailing tour on Lake Michigan. Sip a complimentary drink as you soak in views of landmarks along the waterfront and the Great Lakes. It's the perfect way to experience the Windy City from a new perspective.

You will be treated to a morning of relaxation and fun on Lake Michigan on this sailboat charter. You are in charge of the itinerary, guest list, even music choices! There is a fridge and ice aboard if you would like to bring refreshments (no glass please) and if you are feeling adventurous, you can take a turn at the helm.

On June 18 and 19 2022 ten national teams will race cutting-edge, foiling F50 catamarans – capable of speeds in excess of 100 kph – along the shores of Lake Michigan in front of the Chicago skyline. Mark you calendars this Father’s Day weekend for two-days of speed, drama, and thrills as the entire city kicks off Summer 2022 at Navy Pier! Race times are at 3pm to 4:30pm both days. For a limited number of VIP guests, you can watch Sail Grand Prix aboard Chicago’s Official 148′ Flagship “Windy”. For this special event, Windy will depart Navy Pier at 2pm for a premium viewing area on Lake Michigan. Windy will return by 4:45pm.

Experience the Air & Water Show Aboard 148' Tall Ship Windy. This is a VIP Charter - Truly the Best Seat in Chicago. Leave our dock and motor to center stage for the best viewing of the Air & Water Show. A don’t miss experience. Chicago’s famous Air and Water Show aboard the Tall Ship Windy is truly a magical event. While the official schedule has yet to be announced, it’s anticipated that the US Navy Blue Angels will return again in 2022 to wow audiences — along with appearances by the USAF F-35A Lightning II Demo, Michael Goulian in his acrobatic Extra 330SC, Rob Holland in the MXS-RH, Susan Dacy in her Super Stearman “Big Red”, and antique military aircraft from the Warbird Heritage Foundation. Also watch for the US Army Golden Knights parachute teams, the U.S. Navy Leap Frogs parachute team, as well as other crowd-pleasing stunts by the AeroShell Aerobatic Team, and a performance by the Chicago Fire Department Air/Sea Rescue team.