Water Tours

(18 activities)
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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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    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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    TikiFlotilla with Fireworks

    (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. 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!
    TikiFlotilla with Fireworks

    400 E Monrore St, Chicago

    • Head out to Lake Michigan on two 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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    City Lights Paddle

    (28)
    This nighttime adventure is so riveting you're basically guaranteed to wet yourself. Hop into a kayaking and explore the Chicago River during a guided tour in which you over six miles of water. As you row, you'll be mesmerized by the lights of Chicago at night rising high on either side of you and reflecting off of the water all around you. Your guide will point out some of the historical sights along the way, but this ride is more about letting the thrill of an evening excursion take over your imagination and fuel your sense of awe. Whether you've got some experience paddling or a you're a complete novice, you'll appreciate this intimate perspective of the urban landscape. Quench your thirst for fun with journey through the heart of Chicago.
    City Lights Paddle

    1220 W LeMoyne Ave, Chicago

    • Kayak across the city on the Chicago River during this energizing nighttime adventure tour
    • Learn about history and architecture 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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    Fireworks Paddle! / Navy Pier Fireworks Chicago Kayak Tour

    (3)
    Ready yourself for some explosive fun! This kayaking tour sets off about two miles away from Chicago's Navy Pier, and features a relaxed nighttime paddle that will leave you dazzled ... Particularly when you reach your destination just in time to take in a thunderous fireworks display! You'll be in prime position to take in the show as it lights up the water around you. Afterwards, you'll paddle back along the Chicago River to your starting destination, enjoying the nighttime luminescence of the Chicago's towering architecture on either side. Whether you're a novice who's never set foot in a kayak or an experienced river romper, you'll be touched by the poetic beauty of this introspective journey. Just remember to stow your paddle safely if you're going to clap for the fireworks - it's a long trip back if you have to swim!
    Fireworks Paddle! / Navy Pier Fireworks Chicago Kayak Tour

    500 N Kingsbury St, Chicago

    • Embark on an evening kayaking adventure through the heart of Downtown Chicago
    • Arrive at Navy Pier just in time to be in prime position to catch a dazzling fireworks show
    • 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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    3 positive reviews
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    Night Kayak Tour

    (9)
    The city lights are gorgeous at night and the time is always perfect for an evening paddle... except for maybe in the dead of winter. So why haven't you properly experienced it? The tour begins at dusk, and at that point, you'll paddle down the Chicago River to enjoy the city lights reflecting in the river and off the buildings. Gaze into the eyes of the Sears Tower. See the sparkling lights of Navy Pier. Now's the time to embrace just how beautiful this Midwest masterpiece of a city is. With lights on your boat, it's time to explore the city at night!
    Night Kayak Tour

    1220 W Le Moyne St, Chicago

    • Paddle down the Chicago River under the stars
    • Enjoy the city lights reflected in the river
    • Witness the true beauty of the spectacular city with this unique adventure
    • No experience necessary
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    8 positive reviews
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    Wateriders Classic Chicago Kayak Tour

    (3)
    Embark on a river expedition into the heart of one of the nation's great wild frontiers: Chicago. During this urban tour, you'll take to the waters of the Chicago River for an invigorating and unique kayaking experience. Wateriders' tour guides are knowledgeable adventurists, able to show you the ropes if you're a first timer, and full of information about the eclectic downtown architecture that'll be looming on either side of you during the course of the trip. Sights of interest include numerous famous skyscrapers - and bridges that you'll pass directly under. Whether you're a Chicago newcomer looking to get a unique look a the city, or a resident looking for a fun outdoor adventure without having to leave town, you'll find something to embrace on this urban tour. Discover an intimate perspective of the city that no other type of tour can offer...and observe Chicagoans in their natural habitat.
    Wateriders Classic Chicago Kayak Tour

    500 N Kingsbury St, Chicago

    • Enjoy a guided tour along the Chicago River through heart of downtown
    • Learn about some of the history and urban legends surrounding local landmarks
    • 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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    3 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!
    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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    City Tour and River Cruise

    (11)
    Experience the Windy City like never before by embarking on this scenic half-day tour where you'll sightsee by land and water. A narrated coach will take you through the city's South Side and you'll see highlights such as Grant Park, the Loop, and the Shedd Aquarium. In the second half of the tour, you'll board a state-of-the-art yacht and cruise along the Chicago River as you enjoy stunning views of the city skyline. You'll see all the best parts of Chicago while traveling in comfort and style!
    City Tour and River Cruise

    17 E Monroe St, Chicago

    • Experience the beauty of Chicago from both land and water on this comprehensive half-day tour
    • Discover the history and culture as you visit sites such as Grant Park, the 'front lawn of the city,' and the Adler Planetarium
    • Admire the breathtaking city skyline from the water as you travel on a beautiful streamliner yacht
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    11 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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