Cultural & Sightseeing

(170 activities)
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    Chinatown Walking Tour

    Chicago Chinese Cultural Institute
    What's a better way to experience Chinese and Chinese-American history, architecture, and culture than by exploring Chicago's Chinatown? On this walking tour you will explore this unique area while stopping at many notable gift stores, teahouses, bakeries, and candy stores that help define the area. Make your way past fascinating locations such as the St. Therese Chinese Church and Chinatown Zodiac Square. You'll explore over five blocks of this fascinating, culturally-rich neighborhood while taking in all it has to offer. Leave feeling like you've had a full experience exploring Chinatown!
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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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    River Walk Sightseeing Tour (Summer)

    Chicago's Finest Tours
    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.
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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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    Front Yard Running Tour

    City Running Tours Chicago
    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.
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    Chicago Walking History Tour (Summer)

    Chicago's Finest Tours
    Did you know Chicago used to be a massive swampland that merely intersected the Chicago River and Lake Michigan? Nothing existed, and back then, you'd never guess a skyscraper could stand on such land. Well, today's quite different. This walking tour dives into Chicago's history from stormy swamp to alpha city. As you travel through the streets, listen to the entertaining guides describe the various events that shaped Chicago into one of the prettiest and most successful cities in the world. Visit architectural masterpieces and iconic portraits that distinguish Chicago as one of the best.
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    Chicago Segway Art & Architectural Tour

    See Chicago's landmark architecture, outdoor sculptures and famous skyline by Segway! Before your tour begins, you'll have a 15-minute orientation to get familiar with the Segway. Then you're off gliding through beautiful Grant Park where you will pass by Buckingham Fountain, Lincoln Statue and the Museum Campus. Glide around Millennium Park, where you'll see the work of world-renowned architects, planners, artists and designers. Continue along Michigan Avenue home of the Chicago Water Tower, the Art Institute of Chicago, and the Magnificent Mile. This two-hour, family-friendly guided tour is both an exciting and educational way to explore Chicago.
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    Badass Bitches Tour

    Museum Hack
    We’re not trying to spill any (bean)s, but widespread feminism is still not a reality- especially in the art and museum world! Join a group of badass females, and take a guided tour of The Art Institute of Chicago. Celebrate the female artists who broke barriers to have their art noticed, while also learning about the women artists who the patriarchy sought to keep oppressed! Make friends, fall in love with new art, and most importantly, chip away at the patriarchy. The future of art is female!
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    Chicago Ghost Tour

    Free Tours By Foot Chicago
    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.
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    Bucktown and Wicker Park Beer Tour

    Things to do in Chicago
    Are you interested in going on a three-hour walk? If you said yes, you're probably just being polite. But what if we told you there's BEER involved -- really, really good beer. Discover Chicago's finest beer on this three-hour walking tour of the Bucktown and Wicker Park neighborhoods. With a knowledgeable guide, you'll learn about Chicago's history related to immigration and brewing -- from the late 1600s to the present day -- and visit bars, restaurants, and other locally owned establishments, including the bar that doubled as "Molly's" on the TV show Chicago Fire. You'll also enjoy a Chicago-style hotdog and get a look at some of the city's historical architecture. So let's see: You've got exercise, beer, hot dogs, and architecture. Yep, I'd say that checks off just about every box!
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