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The exciting boat tours have creative, inspiring, and educational elements to keep the people entertained. Set sail today or buy your tickets in advance—we’ve got more boats and more departure times to fit your schedule. Select Show departures next to the tour you’re interested in below, and then click on your desired departure time. Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail. Feel the wind in your hair (and fur!) on a memory-filled river and lake cruise adventure with your best friend.
Seadog Lakefront Speedboat
Enjoy happy hour drink specials onboard this Navy Pier Boat Tour every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Experience breathtaking views of Chicago from the water!
Tour the Windy City from the water
Take in the city’s magnificent architecture bathed in golden light as it begins its transition from day to night. The Tall Ship Windy is a must thing to do at Navy Pier. Very friendly and funny staff and always a good time, with beautiful views of the city of Chicago. Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer. No tours available for this day.Please note, fireworks tours typically run on Wednesday and Saturday evenings during the summer.
Chicago Skyline Sail
Our boats are docked on the slip of water off the Chicago River called Odgen Slip. Cruise down the Chicago River for 90 minutes as you listen to our expert guides discuss the history, impact and legacy of Chicago's renowned architecture. View over 40 Chicago landmarks on our Architecture Tour as you listen to our expert guides tell you how Chicago’s buildings and engineering made the city famous. There is simply no better way to experience Chicago’s world-famous skyline than on a Windy City Boat Tour with Tall Ship Windy. Our Skyline Cruise takes you out onto Lake Michigan, heading both north and south on the lake, you’ll see many of Chicago’s famous landmarks and the classic skyline vista.
The Official Flagship of the City of Chicago
For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. During summer season, you can even choose to upgrade your Chicago Dinner Cruise to include a spectacular fireworks display on Wednesdays and Saturdays. You get the opportunity to witness the spectacular show from the decks of the ship as the gorgeous sky is all lit up at night.
Recalling the handsome elegance of 20th century luxury yachts, our vessels are sure to make an impression. Choose from seven perfectly sized ships for your private event. Chicago CityPass saves 48% on premier admission tickets to Chicago’s top 5 attractions, including the Architecture River Tour. AMDI anticipates a public offering price between $3.50 to $4.50.
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To enjoy the Chicago Odyssey Dinner Cruise in the best possible manner, arrive well before the departure time and dress in your most festive attire. You get to enjoy the electric atmosphere of Navy Pier, alive with entertainers and remarkable views. These Chicago dinner cruises on Lake Michigan are operated by top dinner cruise lines including Spirit of Chicago Dinner Cruise and Odyssey dinner cruise Chicago. Head out on our traditional tall ship and explore the majesty of Lake Michigan while Windy sails across our beautiful lakefront Chicago skyline. From the world-famous Tall Ship Windy, experience the phenomenal sun setting across the Chicago Skyline.
Chicago Odyssey Dinner Cruise
There are three climate-controlled dining decks featuring a unique setting with understated Art Deco accents, which is reminiscent of the classic ocean liners. One of the highlights is visiting Captain’s bridge, which is open to all passengers throughout most of the cruise. It was a very educational and relaxing seventy-five minutes. Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy. Join us at Paradise Adventures in Panama City Beach, Florida, where sun-kissed shores await.
The classic speedboat journey through the waters takes you through blissful elements of a quick view of the magnificence. A round up of fun events, exclusive deals and happenings along Chicago’s Magnificent Mile. The Magnificent Mile is in the heart of Chicago's famous culinary scene and offers visitors a delectable spread of places to dine. Shops along The Magnificent Mile include more than 450 retailers, including flagship experiences, major department stores, and international designers and boutiques. Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides.
Spring and fall tour times are added as weather permits. There’s no better place to view Chicago or Lake Michigan than aboard 148′ S/V Windy; the Official Tall Ship Ambassador for the City of Chicago. Don’t miss these scenic and educational cruises from Chicago’s famous traditional tall ship!
TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour. The crew is fantastic and the tour guide is hilarious. His sense of humor really sets this tour apart from the rest, while still offering interesting insights on the city’s unique skyline. Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.
Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies. Follow @mercurycruises on Instagram, Twitter and Facebook to see latest cruise information, special promotions and fun city happenings. As soon as you step aboard, the Captain and crew will greet you and the ship’s photographer will record the moment. When you reach the deck, you are greeted by your host and escorted to a private table. Now the waiting staff will introduce themselves and the experience begins. Choose the seat that gives you the optimal view of the skyline that encompasses every soul on the boat.
Take in the stunning sights of Chicago’s skyline from Lake Michigan—it’s a view of the city like you’ve never seen it before! Our Skyline Lake Tour departs daily from Navy Pier spring through autumn, weather permitting. The menu is truly creative and appetizing consisting of seasonal hors d’oeuvres, appetizers, entrees and desserts and is freshly prepared on-board daily. We provide you with an extensive range of packages and features to choose from for your ultimate boating through tranquility.
Let me inspire you to explore Chicago more with reviews, photographs, and useful tips from my personal experience. Whether you’re a native Chicagoan, newcomer, or just visiting, a Spirit of Chicago brunch cruise is the perfect weekend outing. Explore the city’s beauty as you take a relaxed tour in the waterways that run through every beautiful street. Keep an eye on the sun to see it go up and down to mark the day’s adventures for every visitor in the city. If you are a lover of architecture, select a variety of options to explore the beauty of the city while floating in paradise. Enjoy a lively day in Chicago starting with a one of a kind experience at Ed Debevic's.
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