Walking Tours · Tomorrow

(11 activities)
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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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    Twilight Riverwalk & History Tour

    (25)
    Join Free Tours by Foot for a leisurely stroll along the northern reaches of the Chicago River to take in the surrounding beautiful architecture! Following your expert local guide, you'll learn the fascinating histories of Chicago icons, such as the Tribune Building, Trump Building, and Wrigley Building, and hear the stories behind the men and women who built them. The tour even ends right around the corner from Municipal Pier #2 (better known as Navy Pier), where you can easily stroll over to see the sites including the Ferris wheel, the Stained Glass Museum, and tons of food vendors. Chicago may be known as The Second City, but on this tour you'll discover exactly what makes it first rate!
    Twilight Riverwalk & History Tour

    175 N State St, Chicago

    • Explore the northern reaches of the Chicago River on this informative guided walking tour
    • Snap great photos as you pass the Tribune Building, Trump Building, and Wrigley Building
    • Follow your expert guide to learn the fascinating stories of the men and women who built these iconic buildings
    • Stroll over to Navy Pier to see the Ferris wheel, the Stained Glass Museum, and tons of food vendors
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    25 positive reviews
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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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    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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    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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    Interior Architecture Loop 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.
    Interior Architecture Loop Tour

    10 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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    Loop and Millennium Park Tour

    (25)
    Join Free Tours by Foot for the most interesting and informative way to experience Chicago's downtown area called the "The Loop," also known as the Theater District! Defined by the elevated train lines that form a circuit in the heart of the city, the Loop is Chicago's commercial core, home to big names such as Boeing and IBM. But, it's so much more: The Loop contains the largest concentration of skyscrapers, including the tallest in the United States and it is effectively a living architectural museum, with a large range of architectural styles, from Victorian to post-modern. 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 these many fascinating styles of architecture that the city offers. Pay a visit to Marshal Fields before stopping for a photo opportunity at City Hall and the iconic Sears Tower. Take a selfie at the start of the legendary Route 66 and discover the Chicago Pedway, 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!
    Loop and Millennium Park Tour

    175 N State St, Chicago

    • Explore Chicago's downtown area known as "The Loop"on this guided walking tour
    • Follow your guide through Millennium Park to see the sculpture that everyone calls "The Bean"
    • Capture photos at the start of the legendary Route 66 and capture sights of the iconic Sears Tower
    • Learn how "The Second City"rose from the ashes after the Great Fire of 1871
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    25 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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