Cultural & Sightseeing · This Weekend

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    The Original Chicago Pizza Tour

    (11)
    Experience an unmatched culinary experience on the only bus driven pizza tour! You'll explore several of Chicago's neighborhoods in search of tasting Chicago's most defining food... PIZZA! Along the tour, see interesting and historical sights and landmarks as you see Chicago one bite at a time! Each tour will visit a mix of culturally significant and neighborhood pizzerias, enjoying a full serving at each restaurant. Of course, all 4 pizzerias visited are very different in taste and style to ensure the ultimate dining experience. At some restaurants, you even get a "backstage pass" into their kitchens to check out the ovens, ingredients, and overall process. Stops vary from day to day, but rest assured every place selected has a dynamite slice and a friendly atmosphere. Make sure you're ready to eat and experience how these magnificent pizzas span more than a mile.
    The Original Chicago Pizza Tour

    61 E Madison St, Chicago

    • Taste your way through several Chicago neighborhoods with delicious pizzas
    • Visit interesting historical sights and landmarks as you take a bus around the city
    • Eat at four different pizzerias and uncover the varying styles and tastes of each pizza
    • Dive into the kitchen and check out the ovens, ingredients, and processes behind each pie
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    11 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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    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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    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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    Chicago Pedway Walking Tour (Saturday)

    (1)
    Connecting many of Chicago's famous and lesser-known landmarks is a network of heated tunnels, bridges, passages and walkways. Your guide will take you on a 90-minute walk through the Pedway, highlighting a different side of Chicago. Doubling as a comedian, your guide will present to you a historical, interesting, and new perspective on Chicago's Pedway that dates back to WWII. You'll learn about how Mayor Richard J. Daley acquired the famed Pablo Picasso sculpture, as well as see the portion of the Pedway where the Dark Knight movie was filmed. Discover a side to the Windy City too often unseen!
    Chicago Pedway Walking Tour (Saturday)

    100 W Randolph St, Chicago

    • Traverse the heated tunnels, bridges, passages, and walkways that connect many of Chicago's famous and lesser-known landmarks
    • Enjoy a comedic, yet historical, perspective on Chicago's Pedway that dates back to WWII
    • See Chicago from a new perspective as you listen to stories about everything from Chicago's mayors to where portions of the Batman: Dark Knight movie was filmed
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    1 positive reviews
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    Architecture of the Loop Walking Tour

    Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors of the Marshall Fields Building, Chase Tower, Chicago Cultural Center and more, plus see public art by Chagall and Picasso. Stroll through elegant lobbies, under glittering domes and into the sprawling network of Chicago Pedway tunnels. Your expert guide shares insights about the city's diverse architectural styles and history, bringing the details of the Windy City into vivid focus. Your tour starts out as you meet your guide at Chase Tower to start your exploration of the Loop's interior architecture. Expect to walk a half mile (0.8 km) during an easy 2-hour walking tour with plenty of stops. Your guide shares expertise in architecture, design, art history and history, and provides participants with iPads that show archival images such as maps, historic photos and documentary video clips. Walk through the Marshall Field's Building, where you'll see famous elements of this iconic edifice, including its beautiful atrium and a Tiffany & Co-designed mosaic ceiling. Ponder the design of the very modern Block 37 complex, situated in the heart of the Loop at a trend-setting location where the city's first skyscrapers and supermarkets were built. See the extensive public plaza, which sits at the geographic center of the Chicago Loop and features Marc Chagall's Four Seasons mural. Admire another famous piece at Daley Plaza: the untitled Chicago Picasso sculpture, which stands 50 feet (15 meters) tall and was the Windy City's first piece of public art. Look at the city through the lens of the Chicago Pedway system -- a network of ground-level concourses, tunnels and bridges that connects buildings throughout Chicago's central business district. Discover how to maneuver through the Pedway and find your way from underneath the downtown. Your tour concludes at the Chicago Cultural Center, a landmark building where you see a magnificent stained glass dome. It was completed in 1897 and originally was Chicago's first central public library. Afterward, say farewell to your guide and make your way to your next destination.
    Architecture of the Loop Walking Tour

    10 S Dearborn St, Chicago

    • Enjoy a guided tour of Chicago's breathtaking architecture
    • Visit the trend-setting Block 37 complex, home of the city's first skyscrapers
    • See the stunning mosaic ceiling of the Marshall Field's building
    • Explore the Pedway system, a network of tunnels and concourses between buildings
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    Front Yard Running Tour

    (23)
    We know what you're thinking, "been there, done that." But have you "BEAN there, done that"?? Join City Running Tours Chicago for a special workout and tour combo! Starting your tour at the famous "Bean," you'll run through Millennium Park and Grant Park, known as Chicago's Front Yard. See the famous Buckingham Fountain and Cloud Gate, and visit "off the path" sites like the John Logan Sculpture and Agora, all the while learning the surprising history of how Chicago's parks came to be. You'll snap plenty of photos along the way, including one with the city's beautiful skyline behind you. You're about to go hard. ChicaGO hard.
    Front Yard Running Tour

    Central Loop, Chicago

    • Enjoy a running tour through Millennium and Grant Park, AKA Chicago's Front Yard
    • See sites like the Buckingham Fountain, Cloud Gate, the John Logan Sculpture and more
    • Snap a bunch of stellar photos on your way, including one of the beautiful Chicago skyline
    • Get a great workout while discovering a whole new side of Chicago
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    23 positive reviews
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    River Walk Sightseeing Tour (Summer)

    (25)
    Reflecting the beauty of Chicago's skyscrapers, the River Walk provides a relaxing alternative to traversing the bustling city streets. Lush greenery, cafes, and cozy seats adorn the riverside. On this tour, enjoy entertaining stories as you trot along river Confluence, Arcade Civic, and Market districts. Discover fantastic views of the city's iconic skyline, visiting historic locales like Wrigley, Aqua, and Trump Tower. In a matter of hours, you'll walk Chicago's past, present, and future, while reveling in the stories of the city's most colorful characters. Now, that's something truly unique.
    River Walk Sightseeing Tour (Summer)

    111 E Upper Wacker Dr, Chicago

    • Relax in the sun or shade along the Chicago River, hearing about the incredible buildings and the people who built them
    • Take in the spectacular views of Chicago's skyline
    • Hear about Chicago's fascinating characters like William Wrigley Jr., Al Capone, and Helmut Jahn
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    24 positive reviews
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    Haunted Chicago Segway Tour

    (18)
    Steeped in violence, mafia-related crimes, and deadly fires that claimed hundreds of thousands of lives, Chicago's a city filled with haunts. On this tour, you'll glide around the streets of Chicago on a Segway, stopping at places like the Michigan Avenue hotel, allegedly the most haunted hotel in the city, and Death Alley, where victims of the terrible Iroquois Theater fire were found. At these eerie locales, hear stories about the creepy things that've happened like unexplainable deaths and self-playing pianos. Pass the site of the Iroquois Theatre fire where over six-hundred Chicagoans perished in a single day. Here, you'll have fun in the creepiest of ways. Just make sure you're sleeping with one eye open at night...
    Haunted Chicago Segway Tour

    300 E Monroe St, Chicago

    • Feel chills standing at infamous haunted hot spots throughout Chicago, such as Death Alley and the former site of Fort Dearborn
    • Glide on a Segway through the city streets to creepy locales like the Michigan Avenue hotel, considered the most haunted hotel in Chicago
    • Learn the stories and tales behind the ghosts that haunt the city today
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    18 positive reviews
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    Chicago Ghost Tour

    (11)
    The Windy City is known for her food, architecture, and haunting history! Join this walking tour as the sun sets through downtown Chicago, and hear some of the most gruesome and creepy local stories recounted by your expert guide. First stop is the Congress Hotel, known as the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey. Then, visit Death Alley and the site of the Eastland Disaster, and catch a glimpse of Chicago's sordid past through stories of the Everleigh Club, the 1900's Red Light district, and famous downtown prison breaks. But consider yourself warned: this tour is not meant for the faint of heart, taking only those who seek a good thrill and are interested in the underbelly of Chicago.
    Chicago Ghost Tour

    520 S Michigan Ave, Chicago

    • Enjoy a spooky insider's look at the haunted history of The Windy City on this after hours walking tour
    • Visit the locations where H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey
    • Hear stories of gruesome and creepy happenings in Chicago
    • Gain a unique perspective on Chicago, and mingle with fellow tour goers
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    11 positive reviews

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