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— Cruises & Sailing
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    Lunch Cruise

    (17)
    Tired of the same old boring lunch? Treat yourself to a long lunch break and board Chicago's largest luxury yacht. With a drink in hand, and a beautiful view of the Windy City, order a three-course meal from the celebrity-chef inspired menu, but bring your appetite because the food on deck is absolutely delectable, plentiful, and freshly prepared. Throughout the cruise, DJ entertainment will set the mood -- how's jazz for your ears? Upon returning to the pier, you're guaranteed to be relaxed and refreshed. Use your lunch break wisely because it doesn't get much better than this.
    Lunch Cruise

    600 E Grand Ave, Chicago

    • Board Chicago's largest luxury yacht for a delectable lunch
    • Enjoy a freshly-prepared, celebrity-chef inspired, three-course meal, and beautiful views of the city skyline
    • Relax to the sounds of Lake Michigan
    • DJ entertainment will be provided to lighten the mood
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    17 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

    17 E Monroe St, 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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    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

    17 E Monroe St, 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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    Chicago Dinner Cruise (Weekday)

    (17)
    What's better than a three-course meal? A three-course meal on the water! Newly renovated, this luxury vessel features a newly furnished rooftop lounge, posh atmosphere and stylish interior. Upon boarding, the Captain and crew will greet and escort you to your private table. From there, you'll be able to check out the observation decks, filled with understated Art Deco accents and reminiscent of the classic ocean liners. Next, you will feast on a splendid 3-course meal with celebrity-chef inspired dishes prepared from fresh ingredients right on-board. Finally, dance the night away to DJ entertainment or simply relax in the elegant ambiance and admire unparalleled views of the famed Chicago skyline as you glide along the shores of Lake Michigan. Why eat at your usual restaurant spots when you can dine in style... on the water!
    Chicago Dinner Cruise (Weekday)

    600 E Grand Ave, Chicago

    • Board a luxury vessel that features a newly furnished rooftop lounge, posh atmosphere, and stylish interior
    • Dine on a three-course meal prepared with fresh ingredients
    • Enjoy the nighttime entertainment, including DJs, unmatched views of the skyline, and an elegant ambiance
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    17 positive reviews
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    Tiki Pontoon

    (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 even choose where you want to boat to end up. So what are you waiting for? Get out there and cut loose!
    Tiki Pontoon

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on one of Chicago's premier party boats
    • Enjoy a fun ride in the sun and some incredible views of Chicago's skyline
    • 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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    Sunset Dinner Cruise

    (17)
    What does a night out in Chicago need? Dinner? Dancing? Maybe a glimpse of the city's charm and beauty? Have it all on this Chicago Sunset Dinner Cruise. Aboard a three-hour luxury cruise on Lake Michigan, you'll encounter attractions such as Navy Pier and Soldier Field as you dine on a lavish, all-you-can-eat buffet! See spectacular views of the city skyline, while being entertained by a singing ship staff and a live DJ spinning your favorite songs. The sumptuous all-you-can-eat buffet is complete with everything to keep your stomach satisfied. As you enjoy your meal in the elegant setting of the ship's dining room, you'll be entertained by the colorful characters of the ship's cabaret. Let the city enchant you with a wonderful night out!
    Sunset Dinner Cruise

    600 E Grand Ave, Chicago

    • See spectacular views of the Chicago skyline aboard a luxury cruise on Lake Michigan
    • Encounter attractions like Navy Pier and Soldier Field
    • Be treated to a sumptuous all-you-can-eat buffet, complete with a carving station
    • Enjoy the entertainment of a live DJ
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    17 positive reviews
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