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Grab a group of friends and book a table – ideally one with a window-facing view—for a buffet-style meal before making your way to the dancefloor for an evening of DJ-curated music. Unlimited coffee, tea, and water will be on hand. Sure, walks along Michigan Avenue and State Street are nice and rooftop bars offer plenty of pretty sights – but the best way to see downtown Chicago is from the water. History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy.
Admire architecture with Chicago’s First Lady
Want to see Chicago from the water but don't have much time to spare? You can peep the skyline in just 30 minutes on Shoreline's Classic Lake Tour, which departs from Navy Pier and boasts some of the best views you'll find on Lake Michigan. If you're weighing your options, Wendella's architecture tour (which it claims is Chicago's original) is another way to explore all of the beautiful structures that line the river. Over the course of the 90-minute tour, you'll navigate all three branches of the Chicago River, while your guide fills you in on the stories behind some of the skyline's most prominent edifices. This tour departs from the Wendella Dock, located at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building.
Shoreline Architecture River Tours
Their glass-enclosed river vessel is particularly stunning. It offers passengers panoramic views of the city’s most iconic buildings as you glide along the Chicago River. They also offer lakefront brunch and dinner cruise options that depart from Navy Pier. Let the wind carry you to stunning views of the city from aboard the Tall Ship Windy, a four-masted, 148-foot topsail schooner. The 75-minute trip cruise brings guests on a scenic route running along the Lake Michigan shoreline, where you can take in lovely skyline vistas and glimpses of the sunset. Head to the onboard bar to find snacks and drinks for sale.
Lake Michigan Skyline Sightseeing Cruise
For more than 25 years, the CAC's expertly trained docent volunteers have led the CAC River Cruise, sharing fascinating stories behind more than 50 buildings along the Chicago River. Hear how Chicago grew from a small settlement into one of the world's largest cities in less than 100 years. In just 90 minutes, you'll get the best overview of Chicago’s architecture and its history.
Take in Chicago’s iconic skyline and the scenic Chicago River with sightseeing cruises at Navy Pier! These fun experiences offer guests panoramic city views along with entertaining and enlightening commentary about Chicago’s architecture and history. Embark on a 90-minute (approximate) sightseeing adventure aboard our most popular daily tour. See Chicago from the unique perspective of the river and lake and learn about the city as our lively guides take you on a journey filled with tall buildings and taller tales.
On these 30-minute speed boat rides, you’ll tear across Lake Michigan at up to 45 miles per hour while getting entertaining and informative commentary on Chicago. 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. Wacker Drive into your GPS.Located at the northeast corner of Michigan Avenue and Wacker Drive, a black awning marks the boat dock entrance stairs that lead down to the river.
Find Your Experience
Hop on a boat at Navy Pier or on Michigan Avenue. 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. Around the world, Chicago is known for its outstanding architecture, and it’s easiest to admire the city’s legacy from the water. By partnering with the Chicago Architecture Center, Chicago’s First Lady offers the most comprehensive tour of the skyline — docents must train 100 hours before they can lead tours. For three generations, Wendella Tours and Cruises has been cruising the Chicago waterways.
If you’re looking for other ways to sail, we invite you to explore our other exciting locations! Tall Ship Windy is proud to be a part of the Amphitrite Digital family of companies. Chicago's Leading Lady, Chicago’s Classic Lady, and Chicago's Emerald Lady are wheelchair-accessible. These vessels cruise at the 9am, 10am, 11am, 12pm, 1pm, 2pm, 3pm and 5pm departure times. When boarding, guests cross two ramps and enter through a 36-inch-wide opening (doorway). Crew members will assist in guiding the wheelchair across the gangway.
Enjoy a three-course gourmet dinner on the water in the Odyssey Chicago, where you can enjoy breathtaking views of the skyline surrounding you. Departing from Navy Pier, this cruise includes a dinner with freshly prepared entrées, mains, and desserts. The 2.5 or 3-hour ride takes you around Lake Michigan, with a cash bar to keep the drinks flowing throughout your meal. While Chicago’s summer fireworks are already fun to watch, it’s an entirely new experience when you’re on a 3D tour.
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One of the best ways to see Chicago is from the water. The city is home to two stunning waterfronts — the Chicago River and Lake Michigan — and each offers plenty of cruise options. Here’s your guide to Chicago lake and river cruises, boat tours, dinner cruises, and beyond. There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail.
Departing from Navy Pier's Polk Bros Park or the northeast corner of the Michigan Avenue Bridge, this 60-minute trip packs in all of the architectural sights that visitors want to see. Tour guides highlight more than 40 towering Chicago landmarks, including the Tribune Tower, the Wrigley Building, and Marina City (a.k.a. "The Corncobs" or "The Wilco Building"). I’m a life long Chicagoan and I brought my out of town relatives on this cruise and we all loved it!
Grab a group of up to six friends and book a private cruise aboard Lady Grebe, a 48-foot vintage yacht that can be reserved for two-hour trips along the Chicago River. The reservation comes with a premium drinks package and you can also opt to kick things up a notch with picnic baskets full of food or full-service catering. If you balk at the idea of traipsing around museums and galleries all day with just your legs for locomotion, this whistle-stop boat ride is the tour for you. See every worthy Chicago landmark in 30 minutes on Seadog’s speedboat, which can sometimes feel like a floating rollercoaster. Launching from Navy Pier, the captain will efficiently guide you (with a running commentary) around Lake Michigan, past Museum Campus, Magnificent Mile, Grant Park, and more.
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If you have limited mobility, see these directions for an alternative way to reach the dock. Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions. Sign up for our email to enjoy Chicago without spending a thing (as well as some options when you’re feeling flush). Feel the spirit of centuries past and hoist the sails as part of your Chicago boat excursion on Tall Ship Windy. AMDI anticipates a public offering price between $3.50 to $4.50.
With its variety of tour options, cruise times and lengths, and a heated, enclosed cabin, Wendella is a great choice for families looking for flexibility. Choose from lake & river architecture, sunset cruises, and more. Host an event unlike any other in the city! Book your group aboard one of Spirit’s regularly scheduled lunch, brunch, cocktail or dinner cruises, or... Odyssey Lake Michigan presents special prix fixe dinner cruises, offering guests the opportunity to try one of Chicago’s most unique dining experiences at an incredible... That’s what’s on offer with this Chicago River tour.
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