Walking Tours · Tomorrow

(11 activities)
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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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    Bridge Lift Walking Tour

    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.
    Bridge Lift Walking Tour

    E Upper Wacker Dr, Chicago

    • Watch the spectacle of the Chicago bridge lift as sailboats migrate from Lake Michigan to winter storage
    • Learn the history behind these structures, discussing the hows and whys behind the bridge lift
    • Walk along the Chicago river and check out the boats and bridges
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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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    Morning Stroll: Tour of Chicago's Bridges

    Is there anything more relaxing than a morning stroll? The city's quiet, you can feel the soft breeze from Lake Michigan. It's Chicago at its most peaceful time. With Chicago Loop Bridges, enjoy a scenic walk from Ellen Lanyon's Riverwalk Gateway to the McCormick Bridgehouse and Chicago River Museum. Along the way, you'll explore some of Chicago's bridge history, the 1909 Plan of Chicago, and how a Chicago-type bascule bridge operates. As you walk and learn, take in the best views of this city. It'll remind you why it's one of the prettiest in the world.
    Morning Stroll: Tour of Chicago's Bridges

    E Upper Wacker Dr, Chicago

    • Explore Chicago's bridge history, the 1909 Plan of Chicago, and even estimate the age of Chicago bridges
    • Walk along the river as you observe these bridges in action
    • Visit the McCormick Bridgehouse to gain a better understanding of bridges in Chicago's history
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    Chicago Grand Half-Day Tour

    (26)
    If you're looking for the most comprehensive, in-depth tour of Chicago, you may want to schedule the Grand Tour, a half-day tour that showcases everything famous and interesting there is to see in Chicago. Discover the highlights of Chicago's North and South sides, and enjoy a scenic route along the Outer Drive. Pass by the city's beautiful Washington Park and Grant Park, and make a 20-minute stop at the fascinating Lincoln Park Conservatory. You'll also uncover the magnificent art and architecture that can be found on nearly every street corner as well. Experience the Windy City in all its glory!
    Chicago Grand Half-Day Tour

    17 E Monroe St, Chicago

    • See everything there is to see in this four-hour tour of Chicago
    • Explore the highlights of both Chicago's North and South side
    • Learn about the art and architecture that fill the Windy City's streets
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    26 positive reviews
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    Chicago's North Side Tour

    (26)
    The Wrigley Building, the Magnificent Mile, and Michigan Avenue are just a few of Chicago's North Side hotspots. Venture to and experience the vitality and excitement of the Windy City on this sightseeing tour! This is the famous "Loop" you expect to see when you're in the city. Here, you'll take a narrated coach through the city, seeing Richard J. Daley Plaza, which houses the infamous Picasso sculpture, and a double-decked street. If that's not enough for you, encounter Lincoln Park, visiting the lush greenery, lagoons, and flowers right inside this bustling city. This tour showcases the glitz and glamour of Chicago -- experience it for yourself!
    Chicago's North Side Tour

    17 E Monroe St, Chicago

    • Tour Chicago's North Side, experiencing the vitality and excitement of the Windy City
    • See the Wrigley Building, the Magnificent Mile, and Michigan Avenue
    • Enjoy a narrated coach as your learn about the history and culture behind these iconic Chicago structures
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    26 positive reviews
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    Amazing Scavenger Hunt Adventure (Chicago)

    (8)
    Price is for a group of 2-5 people Looking for a way to turn Chicago into a giant game board? Urban Adventure Quest has created an interactive scavenger hunt that combines the fun of the amazing race with a three-hour sightseeing tour of Chicago. Guided from any smartphone, you'll make your way among well-known and overlooked gems of the city, solving clues and completing challenges while learning local history. Answer questions to uncover the next, secret location. The adventure begins river side among the historic buildings and will take you on a journey through historic landmarks. Experience the rich history, beauty of the bountiful public art, as well as the indelible culture of this great city.
    Amazing Scavenger Hunt Adventure (Chicago)

    320 N Dearborn St, Chicago

    • Compete in a fun, interactive scavenger hunt around the city of Chicago
    • Answer questions and complete challenges to guide you to your next location on the tour
    • Adventure by famous Chicago landmarks such as the Bean and the Magnificent Mile
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    8 positive reviews
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    Lincoln Park and Gangster Tour

    (13)
    Before the Great Chicago Fire in 1871, Lincoln Park was home to German and Polish immigrants, but since the fire only reached the edge, it grew with the "worthy families" who had been forced out of downtown. On this guided walking tour, learn about the fascinating history of Lincoln Park, and how it has become a cultural center and youthful area with nearby DuPaul University and Notebaert Nature Center! Explore the dark side of this neighborhood beyond its beautiful scenery and collegiate history, including the bloody gang killings on Valentines Day and the capture and eventual death of the infamous Depression-era outlaw John Dillinger. Stop by at the Wise Fool's pub before ending your night with passes to the Kingston BLUES club for a fully encompassing Chi-town experience!
    Lincoln Park and Gangster Tour

    2391 N Stockton Dr, Chicago

    • Learn about the fascinating history of Lincoln Park on this informative guided walking tour
    • Explore a cultural center and youthful area of Chicago with nearby DuPaul University
    • Follow your expert guide to hear about the Valentines Day massacre and the death of the infamous John Dillinger
    • Stop by at the Wise Fool's pub, and end your night with passes to the Kingston BLUES club
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    13 positive reviews
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    Loop Interior Architecture Tour

    (14)
    Step inside magnificent lobbies, corridors, and the underground Pedway System for an in-depth look at architecture and a personal, cultural approach to experiencing downtown. Great for any time of year, you'll stay indoors for most of the walking tour. Highlights include a historic department store, a skyscraper church, the infamous Block 37, and the sparkling mosaics of the Chicago Cultural Center. You will also engage with photos and video clips on shared iPads, while a live tour guide shares expert commentary on this architectural and historical tour.
    Loop Interior Architecture Tour

    140 S. Dearborn St, Chicago

    • Take an in-depth look at the architectural interiors of several Chicago landmarks
    • Explore the famous underground Pedway system
    • Engage with photos and video clips at each location
    • Uncover Chicago's marvelous history through architecture
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    14 positive reviews
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    Chicago Loop Tour

    (12)
    Chicago's not known as "The Second City" because it's behind NYC or Los Angeles. It's the Second City to only one, itself. Rebuilt after the Great Fire of 1871, Chicago's one of a few city's to top itself. On this walking tour, you'll see the highlights of the Windy City. Feel those Lake Michigan breezes, and quickly understand the where its nickname came from. Along the tour, you will see Chicago's spectacular sights and stroll about the eclectic architecture. Witness the skyline from ground-level, and learn about the many reasons tourists flock here every year. It's the Loop like you've never seen it before!
    Chicago Loop Tour

    425 N Michigan Ave, Chicago

    • Stroll through Chicago's famous Loop
    • See the sterling skyscrapers and travel throughout the cityscape
    • Learn about Chicago's history and its amazing architecture
    • Discover why this city is called "The Second City"
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    12 positive reviews

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