Cultural & Sightseeing

(181 activities)
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    Chicago Pedway Walking Tour (Saturday)

    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!
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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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    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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    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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    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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    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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    Shady Chicago: Ghosts and Gangsters of Hustlertown (PG13)

    Wateriders Kayak Tours and Rentals
    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.
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    Bridge Lift Walking Tour

    Chicago Loop Bridges
    Watching Chicago's movable bridges operate generally provokes a gasp. "Oh...my." "Woah." "Did you see that?" Walking just around the riverbend, you'll follow the bridge lift, watching these massive kinetic sculptures open for the sailboat migration from Lake Michigan to winter storage. Waving to the sailors, you'll discuss the hows, whys, and history of the current bridges. This is your tour. You can bring up any specific interests you would like to explore. Uncover the mysteries behind these beauties, today, and gasp in wonder at the man-made marvels.
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    Finest of Everything Walking Tour (Summer)

    Chicago's Finest Tours
    Exactly as the name suggests, the "Finest of Everything Tour" explores the city's rich history and glamorous locales. Strolling through the Loop, view and learn about Chicago's finest architecture and artwork, while listening to heartrending tales about the city's disasters. In addition to the scenic walk, you'll uncover Chicago's underground Pedway system and enjoy a boat ride along the river. Told you, it brings the finest of everything together! You'll laugh; you'll cry; and it'll take your breath away.
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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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