Special Occasion · This Weekend

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    Sunset Dinner Cruise

    (37)
    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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    37 positive reviews
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    Helicopter Tour of Chicago

    (2)
    It's a bird! It's a plane! No, it's you taking in the city sights on this helicopter tour of Chicago! See famous landmarks such as Grant Park, the John Hancock Building, Lincoln Park Zoo, and Wrigley Field like you've never seen them before. During the ride, enjoy listening to your experienced pilot share his vast knowledge of the city's history and recommended spots to check out. You'll even get to enjoy the most exciting game of tic-tac-toe you've ever played using Chicago's famous grid system. So strap in, buckle up, and get ready for liftoff. Until you've seen Chicago from above, you've only seen half the picture!
    Helicopter Tour of Chicago

    1339 S Wood St, Chicago

    • See Chicago's famous sites as you glide safely above the metropolis in a helicopter
    • Enjoy a bird's-eye view of tourist attractions such as Navy Pier, Soldier Field, and the Adler Planetarium
    • See the city's photogenic architecture on this one-of-a-kind experience
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    2 positive reviews
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    Tiki Pontoon

    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

    Monroe Harbor, 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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    Lake Michigan Shore Wine Tour

    Forget California. Forget France and Germany. There are some wonderful wines produced right here in the Midwestern states of Michigan, Illinois, and Wisconsin. Join an adventure through the Lake Michigan Shore Wine Trail, settled on the Eastern shores of Lake Michigan - a terrain that hosts numerous microclimates which make the region's wine diverse and unique. You'll visit 3 wineries sprinkled throughout the area on this eight-hour tour. Experience the lush countryside, home to over 10,000 acres of grapes. If you like wine, which you obviously do, then taste the best of the Midwest.
    Lake Michigan Shore Wine Tour

    505 N Michigan Ave, Chicago

    • Discover a variety of wines found right in the Midwest
    • Visit three wineries sprinkled throughout the city and uncover the region's diverse and unique wine characteristics
    • Explore the lush countryside that houses over 10,000 acres of grapes
    • Taste your way through the one-of-a-kind flavors of Midwest wines
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