Top Chicago Cruises & Sailing - page 2

Chicago is famous for its architecture, and the best way to see it is on a cruise down the Chicago River. Glide by historic and modern marvels like the Civic Opera House, Wrigley Building, and Willis Tower from the comfort of an open-deck boat. Live narration reveals each building’s fascinating history, so you'll learn more than you would just observing on your own.

Most people have to decide between a boozy Sunday and a river cruise. During this special boat ride in Chicago, you get the best of both worlds. Enjoy a range of mimosas and other brunch drinks for purchase as you cruise down the Chicago River. Enjoy front-row seats as you pass by iconic skyscrapers and other downtown landmarks, with staff available to answer your questions.

Experience Chicago’s fireworks like never before on a river cruise with 3D viewing glasses. Cruise past major sights like Buckingham Fountain, Museum Campus, and the John Hancock Building while learning about the city's history from your onboard guide. Capture stunning skyline photos and enjoy front-row views of the dazzling fireworks from the mouth of the river.

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

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.

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

Admire Navy Pier’s fireworks from the best possible vantage point: the water. On this luxury Lake Michigan dinner cruise, you’ll enjoy front-row seats for the spectacular display (weather permitting) while digging into a plated and chef-prepared gourmet meal. A DJ is on hand to set the mood and spin some tunes, with craft cocktails for purchase.

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

On most tours of Chicago, you only see a small selection of the city’s highlights, but you can customize this flexible-duration private tour to suit your schedule and tastes. Choose to discover hidden gems that most tourists miss, snap photos of landmarks like the Willis Tower, explore the Windy City’s shopping scene, and much more.

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!

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.

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic stops ✔️ Zero wasted time ✔️ Only the best views, landmarks, and photo spots We don’t stall, we don’t drag things out — and when we say “See All of Chicago,” we mean it. From skyline views and lakeside gems to architectural icons and hidden local favorites, our guided route is packed with unforgettable stops — and none of the filler. Let’s explore the city — the right way.

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.

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.

Don't worry about finding your own way to or from the airport: with a private airport transfer service, you can navigate Chicago without worry. Choose between various luxury vehicle options, including an executive sedan, first-class sedan, and SUV, and meet your driver directly at your Chicago address or at your arrival gate. Then, enjoy a stress-free ride through the Windy City directly to your destination.

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Along DE way, it connects iconic cities such as St. Louis, Tulsa, Amarillo, Albuquerque, Flagstaff and Los Angeles, offering a unique experience through varied landscapes, from the Midwest Plains to the Southwest Deserts, each with its own history and culture. Route Chicago : 50 points Route DE Chicago to St. Louis : 56 points Route San Luis : 13 points Route DE San Luis to Joplin : 56 points Route Joplin to Oklahoma city : 29 points Route DE Oklahoma City to Amarillo : 27 points Yellow Route to Santa Fe : 39 points Route DE Santa Fe to Las Vegas : 80 points Route DE Las Vegas to Los Angeles : 34 points Total DE DE DE DE l’Or points of interest: 384

Captain Greg and his wife First Mate Cait are world-class sailors. Their resumé includes a 9-month, 6,000 nautical mile voyage from Chicago to the Bahamas and back from October 2020 to July 2021 completing "America's Great Loop". They share their passion for sailing and affinity for Lake Michigan with guests every year. Your meticulously maintained sailing yacht, a 2003 french-built Jeanneau Sun Odyssey 37, offers the flexibility of adventurous sailing with the option to drop anchor & swim or float on the Lake. It is the best private experience in the heart of the city. Your Chicago sailing charters are perfect for summer birthdays, romantic proposals, anniversaries, and more. Take in the sights, sounds and breathtaking scenery of the Chicago Lakefront. From adventurous sailing to relaxing sunset cruises, float parties, Navy Pier fireworks and plenty of special events throughout the year- we have something for everyone!