Air & Water

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    Sunset Cocktail Cruise Aboard Mystic Blue in Chicago (Monday Night )

    Most people can agree that Mondays are the worst. But maybe they don't have to be so bad if you've got a cocktail cruise to look forward to! Climb aboard the Mystic Blue Yacht for a relaxing, after work sunset cruise! From the famous Ferris Wheel to the Lake Michigan shore, the sights and atmosphere of Chicago's Navy Pier make it the perfect place to spend an evening relaxing! If you feel the need to unwind even more, you'll get the chance to dance to the sounds of one of Chicago's hottest live DJ's. Plus, there'll be a fully stocked cash bar where you can pick up your favorite cocktails! This will be a party for the books.
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    Sunset Cocktail Cruise Aboard Mystic Blue in Chicago (Monday Night )

    600 E Grand Ave, Chicago

    • Make your Monday even better with a party aboard the Mystic Blue Yacht
    • Enjoy beautiful views of the sun setting behind the Chicago skyline
    • Sip on your favorite cocktail while you mingle and lounge with new friends
    • Dance the night away and forget about your worries
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    TikiFlotilla - Prime

    (6)
    For the party so wild that one boat won't suffice. With Chicago TikiBoat's TikiFlotilla package, you'll enjoy both a 34-foot luxury sailboat and the TikiPontoon, the original Chicago partyboat. The boats will be tied together, so you'll easily be able to hop from one to another, enjoying the features that each boat has to offer. The Pontoon boasts a complementary grill with fuel, a sundeck, and a waterslide. The Tiki sailboat is the apotheosis of intimacy and luxury. From either one you'll be able to enjoy majestic views of the Chicago skyline, while partying in comfort and style. So what are you waiting for? Get out there and cut loose!
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    TikiFlotilla - Prime

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on two 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 Kayak, Dinner, Beer & Bonfire

    Dial up the summertime splendor with a package adventure! You'll begin your evening with a sunset kayak tour down the Chicago River. Paddle in the shadow of the breathtaking Chicago skyline after a short safety brief from the pros. As the sun makes its colorful descent, your guide will let you in on the history of the city's architectural wonders. Once you've worked up an appetite, you'll return to Kayak Chicago and devour gourmet burgers with a hearty side of mac and cheese, courtesy of The Slide Room food truck! You'd best leave room for dessert because you'll conclude your evening with a classic bonfire treat -- s'mores! Throw back a craft beer while you're at it to enhance the fun. This is the adventure you've been waiting for all summer!
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    Sunset Kayak, Dinner, Beer & Bonfire

    1501 N Magnolia Ave, Chicago

    • Embark on a 2-hour sunset kayak tour down the Chicago River, followed by a burger cookout, some delicious craft beer, a bonfire, and s'mores
    • Paddle in the shadow of the Chicago skyline after a short safety brief from professional instructors
    • Devour 2 gourmet sliders with a side of creamy mac and cheese for a filling dinner
    • Indulge in the most perfect summertime evening
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    Land and River Architectural Tour

    (6)
    Sometimes you need to get away from something to really see it. Cruise the storied shoreline of the Western Hemisphere's longest lake in style from the deck of a stunning steamliner yacht. Along the way, you'll get an unobstructed view of one of the United State's most storied cities, making for some perfect photo opportunities. Sites include the business district, the Loop, South Shore neighborhoods, the Chicago river, the Locks, multiple bridges, Navy Pier, and the Coast Guard Station. If you're new to this area, this is a great way to see this spectacular city from a distance while unwinding with a cocktail aboard a luxury boat.
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    Land and River Architectural Tour

    17 E Monroe St, Chicago

    • Tour the Chicago-side of the Lake Michigan shoreline aboard a steamliner yacht
    • View a city skyline, bridges, locks, and piers from a panoramic perspective
    • Capture lasting memories of your Chicago trip with perfect photo opportunities
    • Relax with a beverage while cruising the waters of one of the world's largest lakes
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    2 positive reviews
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    2-Hour Sail

    Looking for a different way to relax? Are the Youtube videos and Netflix movies just not cutting it? Then why not spend a day on the water enjoying the beautiful sights of Chicago on this two-hour sailboat adventure with you and your loved ones? With Two Brothers Sailing Chicago, set sail from Montrose Harbor with a USCG certified sailboat captain and kick-back with the calming waves of Lake Michigan. This is the perfect tour for couples who want to have a romantic time on a private boat with the Chicago skyline as their backdrop. See the Windy City the way it was meant to be seen... from the water!
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    2-Hour Sail

    Montrose Harbor, Chicago

    • Tour Lake Michigan on a two-hour private sail from Montrose Harbor
    • Experience the stunning Chicago skyline from a unique vantage point
    • Enjoy a day relaxing on the water and escaping the stress of everyday life
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    3-Hour Sail

    Looking for a different way to relax? Are the Youtube videos and memes just not cutting it? Then, why not spend a day on the water enjoying the beautiful sights of Chicago on a three-hour sailboat adventure? On this weekend tour, set sail from Montrose Harbor with a USCG certified sailboat captain and kick-back with the calming waves of Lake Michigan. This is the perfect tour for couples who want to have a romantic time on a private boat with the Chicago skyline as their backdrop. See Chicago the way it was meant to be seen... from the water!
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    3-Hour Sail

    Montrose Harbor, Chicago

    • Tour Lake Michigan on a three-hour sail from Montrose Harbor
    • Experience the stunning Chicago skyline from a unique vantage point
    • Enjoy a day relaxing on the water and escaping the stress of everyday life
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