Water Tours · Tomorrow

(6 activities)
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    Architectural Tour

    (28)
    Part adventure, part history lesson. If only school had been this fun! This tour will have you paddling through the heart of Chicago as you take on the urban canyon that is the downtown Chicago River. Along the way, your guide will fill you in on the history of the area, pointing out architectural points of interest and other oddities that will make this journey almost as intellectually satisfying as it is visually riveting. All told, you'll spend several leisurely hours on the water, getting a light upper body workout that will leave you feeling rejuvenated and limber. Whether you've never kayaked before or you're an experienced pro, you'll love this intimate introduction to the city's history.
    Architectural Tour

    1220 W LeMoyne Ave, Chicago

    • Kayak across the city on the Chicago River during this energizing adventure tour
    • Learn about the history and architecture of Chicago as you paddle by several famous sites
    • Let a certified instructor show you the ropes during a safe row
    • Feel adrenaline of adventure consume your senses and fuel your sense of wonder
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    28 positive reviews
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    Sunset Paddle

    (28)
    If you seek a titillating twilight tour, look no further. This kayaking journey will give you a whole new perspective of city of Chicago. You'll be making your way along the Chicago River, surrounded on all sides by reflections of gold as the sun drops below the horizon. You'll paddle for six miles with a licensed guide who will point out some of the unique sites as you pass by, offering up nuggets of architectural fact and history. Whether you have years of experience kayaking, or are picking up the paddle for the first time, you'll find plenty to enjoy during this adventure. That is, if you're not too busy being titillated by the views.
    Sunset Paddle

    1220 W LeMoyne Ave, Chicago

    • Kayak across the city on the Chicago River during this energizing twilight adventure tour
    • Learn about the history and architecture of Chicago as you paddle by several famous sites
    • Let a certified instructor show you the ropes during a safe row
    • Feel the adrenaline of adventure consume your senses and fuel your sense of wonder
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    28 positive reviews
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    Chicago River Ghosts and Gangsters Kayak Tour

    Everybody knows that if you're looking for ghosts and gangsters, there's a few obvious places to look. Ghosts: old houses on hills, cemeteries. Gangsters: Gentleman's clubs and speakeasies. But HERE'S a place you might not think of where you can find stories of both: The Chicago River! Follow your guide through the downtown segment of the Chicago River, which borders city skyscrapers like Willis Tower. As you paddle, you'll listen to sordid tales about the Windy City, including how its explosive boom in the mid-1800s (following the construction of railroads) led to Chicago's gritty side coming out. You'll hear about crime lords, from Big Jim Colosimo, Papa Johnny Torrio, to the kingpin himself, Al Capone. This is a great way to learn about Chicago's darker side!
    Chicago River Ghosts and Gangsters Kayak Tour

    950 N Kingsbury St, Chicago

    • Paddle down the Chicago river while listening to stories about Chicago's seedier side
    • Learn how the railroad boom led to the emergence of a seamy underbelly
    • Get in a great workout while listening to riveting stories
    • Hear about the colorful cast of characters in Chicago's past, including Big Jim Colosimo and Al Capone.
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    Shady Chicago: Ghosts and Gangsters of Hustlertown (PG13)

    (4)
    Get ready to wet yourself...Not because you'll be falling into the Chicago River (hopefully) during this kayaking adventure, but because of the terrifying tales that you'll hear along the way. This evening excursion will have you paddling through downtown, where on either side of you dark buildings and notorious legends loom large. Get a unique perspective at the urban environment that crafted by the likes of Johnny Torrio, Jim Colosimo, and Al Capone. You'll also learn about many of the reportedly haunted spots along the way - relics of the city's bloody past. Whether you're first time kayaker, or have some experience, you'll be in good hands thanks to the trained and experienced adventurist that'll serve as your guide. However, if a semi-transparent Al Capone pokes his head out of the water ... paddle faster.
    Shady Chicago: Ghosts and Gangsters of Hustlertown (PG13)

    500 N Kingsbury St, Chicago

    • Embark on an evening kayaking adventure through the heart of Downtown Chicago
    • Learn about the city's mob-filled past and several supposedly haunted sites along the river
    • Get some light physical exercise while feeding your need for adventure
    • Indulge your sense of adventure without having to leave Chicago
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    4 positive reviews
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    Real Pirates of Lake Michigan Tour

    (27)
    Ahoy! Hoist the anchors. You're about to set off on an adventure unlike any other. On this tour, learn all about the mischievous pirates that once roamed the great inland seas of Lake Michigan. You'll gain insight about the epic battles that took place, as well as the trickery and treasures that made up such a big part of the pirate world. The real question is, are there any sunken ships with treasure at the bottom of the lake? There's only one way to find out!
    Real Pirates of Lake Michigan Tour

    600 E Grand Ave, Chicago

    • Enjoy real stories about pirates of the inland seas
    • Hear about epic battles that took place right on Lake Michigan
    • Learn about the trickery and treasures that were commonplace in the pirate world
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    27 positive reviews
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    Sunset Kayaking Tour

    (5)
    Is there anything more breathtaking than witnessing a sunset over the prettiest city on Earth? This kayak tour lets you take in the sunset from the best vantage point possible -- just remember to breathe. Here, you'll enjoy Chicago at this special time of day, watching the cityscape transform from sunlit urbania to moonlit marvel. Watch as the sunset reflects off the water and downtown skyscrapers. This tour's the absolute definition of indescribable beauty. You just have to see it for yourself.
    Sunset Kayaking Tour

    4318 N Elston Ave, Chicago

    • Witness a Chicago sunset while paddling through the cityscape via kayak
    • Watch the sunset reflect off the water and downtown skyscrapers
    • Enjoy this unique view of the city
    • No experience necessary
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    4 positive reviews
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