Cruises & Sailing · Tomorrow

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— Cruises & Sailing
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    Chicago Skyline Cruise

    (27)
    Sailboat, water, skyline: that sounds like a recipe for the perfect day of relaxation. See Chicago's skyline the way it was meant to be seen from the water. On this beautiful tour of Chicago, hop on a sailboat to kick back and forget about all worries. You'll tour Lake Michigan as you enjoy the gorgeous skyline in front of you. This optimal vantage point is truly one of the most unique and best ways to see the city. So, whether you're a tourist or a local, sit back, relax, and experience Chicago in a new light.
    Chicago Skyline Cruise

    600 E Grand Ave, Chicago

    • Enjoy Chicago's beautiful skyline from a unique vantage point
    • Take a leisurely trip around Lake Michigan on a sailboat
    • Relax with the wind at your back and gentle waves rocking you back and forth
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    27 positive reviews
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    Lake Michigan & Chicago Architecture Speedboat Tour

    (28)
    Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! Bear witness to the dozens of skyscrapers lining the river, including the Sears Tower and the Tribune Tower. From your entertaining guide, you'll learn when and why the flow of the River was reversed, how Chicago architects pioneered skyscraper construction, and a variety of other stories and fun facts of Chicago's history. Then, for a breathtaking view of the city skyline from Lake Michigan, embark on a thrilling speedboat ride along the lake. Could there be a better way to experience Chicago?
    Lake Michigan & Chicago Architecture Speedboat Tour

    600 E Grand Ave, Chicago

    • Relax on a cruise of the Chicago River as your witness its stunning and original architecture
    • See and hear about the many famous skyscrapers lining the river, including the Sears Tower and Tribune Tower
    • Learn about Chicago's architectural history through interesting tales and tidbits
    • Enjoy the thrill of riding on a speedboat as you take in the spectacular views of the city
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    27 positive reviews
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    Tiki Pontoon with Fireworks

    (6)
    Chicago TikiBoat's Tiki Pontoon is the premiere party boat of the Chicagoland Area, and they want to take you out on Lake Michigan for some fun! The Tiki Pontoon is the original Chicago TikiBoat. It comes equipped with a sundeck, Bluetooth enabled stereo, complimentary grill with 3 bags of fuel, and even a waterslide! And of course, you'll also be provided with a cooler and ice for all the booze you'll bring to keep the party going. As if all that weren't enough, you'll also get to see some fantastic, unforgettable views of the famous Chicago Skyline, And for the grand finale, you'll be treated to a fantastic firework show that will leave you breathless. So what are you waiting for? Get out there and cut loose!
    Tiki Pontoon with Fireworks

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on one of Chicago's premier party boats
    • Enjoy great views of the Chicago skyline and a dazzling fireworks display
    • Check out the sun deck, Bluetooth enabled stereo system, and waterslide!
    • Party in style with all of your closest friends
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    6 positive reviews
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    Chicago City Tour with River Cruise

    (26)
    Experience the Windy City like never before by embarking on this scenic two-hour tour of downtown Chicago, also known as 'the Loop.' A minibus with the comfiest seats will take you to the most iconic stops in the city such as Wrigley Field, the Willis (Sears) Tower, Chicago River, the Magnificent Mile, and Navy Pier. Enjoy stunning views of Lake Michigan and take a few moments to bathe in the beauty of this architectural wonder of a city. n the second half of the tour, you'll board an open-tip boat and cruise along the Chicago River as you enjoy stunning views of the city's famed architecture. You'll see all the best parts of Chicago while traveling in comfort and style!
    Chicago City Tour with River Cruise

    The Loop, Chicago

    • Discover Chicago from both land and water on this comprehensive three hour tour
    • Explore the city and discover the rich history and culture as you visit sites such as Lincoln Park, Museum Campus, Navy Pier, and the Willis (Sears) Tower
    • Take in the Chicago's beauty from the water as you climb aboard an open-top boat
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    26 positive reviews
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    River Architecture Tour (Navy Pier)

    (28)
    What is Chicago's distinguishing feature? Is it the size of its pizza? What about the look of its hot dogs? Nope, it's gotta be the skyline. Bringing Chicago's innovative architectural development to the city's vibrant life, explore Chicago's rich history through its iconic landmarks. All of this will be viewed from the scenic Chicago River. Relax on board a cruise vessel as you observe and relish in the towering skyscrapers like Tribune Tower, the Wrigley Building, and Willis (Sears) Tower. Floating along the river, you'll uncover the tactical details behind each building, learning about the architects and designs that truly distinguish Chicago among the prettiest cities in the world.
    River Architecture Tour (Navy Pier)

    600 E Grand Ave, Chicago

    • Enjoy a historical exploration of Chicago's world-renowned architectural landmarks
    • Travel along the Chicago River, and see buildings like Tribune Tower, Trump Tower, and Willis (Sears) Tower
    • Learn about the city's history in architectural development and innovation
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    27 positive reviews
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    North Side Tour with Cruise

    (26)
    The Wrigley Building, the Magnificent Mile, and Michigan Avenue are just a few of Chicago's North Side hotspots. Venture to and experience the vitality and excitement of Chicago on this sightseeing tour! This is the famous "Loop" you expect to see when you're in the Windy City. Here, you'll take a narrated coach through the city, seeing Richard J. Daley Plaza, which houses the infamous Picasso sculpture, and a double-decked street. If that's not enough for you, you'll hit up Lincoln Park, visiting the lush greenery, lagoons, and flowers right inside this bustling city. Then, experience Chicago from the unique viewpoint of the Chicago River. This tour showcases the glitz and glamour of Chicago.
    North Side Tour with Cruise

    The Loop, Chicago

    • Tour Chicago's North Side, experiencing the vitality and excitement of the Windy City
    • Enjoy a narrated coach, learning the history and culture of the city while passing by the Wrigley Building, the Magnificent Mile, and Michigan Avenue
    • See Chicago from a new perspective as you enjoy a cruise on the Chicago River and Lake Michigan
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    26 positive reviews

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