Cultural & Sightseeing

(174 activities)
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    Architecture Fireworks Tours (Navy Pier)

    Shoreline Sightseeing
    Experiencing the architecture of the Windy City is a breeze (good one eh?) with Shoreline Sightseeing's 90-minute river tour. You'll travel all three branches of the Chicago River and leisurely view of more than 40 of the city's greatest architectural treasures. Knowledgeable guides will walk (or maybe float) you through the history of buildings like the Tribune Tower, the Trump Tower, the Wrigley Building, Marina City and more. You'll finish your tour with a spectacular fireworks display by the Navy Pier. Perfect for the architecture or history buff in your family!
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    Fabulous Quintessential Culinary Tours of Chicago

    Things to do in Chicago
    What should a visitor see and do while in Chicago? It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond that it can often be hard to decide where to start. Why not tantalize all of your desires and senses with a 3 hour small- group walking food excursion lead by a professional guide? You'll indulge in 5-6 of Chicago's quintessential staples while feeding your mind with intriguing and rememberable tidbits along the way. Before you know it, you'll feel like a local. Make sure to come hungry, this tour offers more than enough to be considered lunch.
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    Mini Bus Tour

    See it All Sightseeing
    On this tour you'll see Chicago's world renowned architecture and learn about the city's colorful history, including gangsters like Al Capone and John Dillinger. Drink in the beautiful views of a lake that looks more like an ocean, and a river that now runs backwards! Downtown, you'll see Millennium Park, The Loop, Museum Campus, Soldier Field, The Willis (Sears) Tower and more. Then it's up north, to the fashionable Gold Coast (including the original Playboy Mansion), Lincoln Park, and Wrigley Field (legendary home of baseball's Chicago Cubs since 1916). Of course, you'll stop a few times along the way, so that you can get out, stretch your legs and take some pictures of Chicago's many fantastic sights.
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    The Original Chicago Pizza Tour

    Chicago Pizza Tours
    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.
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    Winter Loop Tour

    Free Tours by Foot Chicago
    Remember, it's called the Windy City for a reason! You will need to bundle up for this winter tour of the Loop -- you'll be spending about half of the time outdoors looking up at the largest concentration of skyscrapers, and the other half inside ogling exquisite public buildings and lobbies. Delight in the detailed history lesson of the Great Fire of 1871 and how the city rose from the ashes to become the impressive collection of businesses and buildings it is today. Sights and topics you will cover on the Winter Loop Tour include, but are not limited to, Block 37, Chicago Theatre, Marshall Fields, The Picasso/Daley Plaza, The L (elevated train), Marquette Building, The Palmer House, and The Great Chicago Fire. See Chicago from a new and truly remarkable perspective!
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    City Tour and River Cruise

    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!
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    Loop Highlight Tour

    Free Tours by Foot Chicago
    Join Free Tours by Foot for the most interesting and informative way to experience Chicago's downtown area called "The Loop"! On this highlight tour, follow your expert local guide through Millennium Park to see the famous sculpture that everyone calls "The Bean" (even though it's not a bean at all!), marvel at the work of Picasso and Chagall that decorates random street corners, and learn about the many fascinating styles of architecture that the city offers. You will find the hidden treasures of Tiffany Glass tucked away in public buildings all while learning the history of how Chicago came to be -- and then how it did it all again after the Great Fire of 1871. Chicago may be known as The Second City, but on this tour you'll discover exactly what makes it first rate!
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    Haunted Chicago Segway Tour

    Do you believe in ghosts? If not, you may start to after this tour. As you follow your guide through the streets of Chicago on a personal Segway, you'll travel down secluded alleys, visit hotel lobbies, and glide along the Chicago River, listening as your guide recounts terrific tales of the city's haunted past, including disasters and gangster murders. Was that just a breeze you felt on your neck? Feel goosebumps on your arms and legs as you stand in the alley where more than 600 Chicagoans perished in 1903. Listen for the faint sound of an unmanned piano playing in the ballroom of the Michigan Avenue Hotel. Stand at the shore of the Chicago River -- the sight of Chicago's most tragic maritime disaster that claimed the lives of 800 people in 1915. Watch out, you don't want to become the haunter.
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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.
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    Chicago Pedway Tour

    Free Tours by Foot Chicago
    If you're a history buff and you love learning about the hidden parts of famous cities, this tour of the Chicago Pedway system will tickle your fancy -- regardless if you're a native or a foreigner. Through a mostly indoor tour, you will discover the secret system of pathways throughout downtown Chicago, which today connects over 50 buildings, 40 blocks, and 5 miles of pathways. You will see a ton of beautiful architecture and art while learning about the history of how they got there. On top of that, you'll also be shown some of the best spots for food the city has to offer. During your tour you will view a number of great sites including, but not limited to, The Chicago Theatre, The Marina Towers, The Leo Burnett Lobby, The Thompson Center, City Hall, and The Cultural Center. See Chicago from a new and truly remarkable perspective!
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