chicago walking tour

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    Loop and Millennium Park Tour

    (26)
    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

    1 W Wacker Dr, 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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    26 positive reviews
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    Chicago's Disasters Tour

    (6)
    Casual walking tours with tame sights and reserved experiences aren't for everyone. This tour combines the inevitable urban mayhem that the city of Chicago has experienced with the unfortunate incidents it has endured throughout the years. This fast-paced, mile and a half of outdoor walking, escalators, stairs, and revolving doors will take you from the underground Pedway to the ghosts swimming in the Chicago River. Expect more ghost stories, creepy alleys, and tales of human folly (including an "unfortunate" event involving Dave Matthews Band and an important body of water). If this piques your interest, you've found the right tour!
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    Chicago's Disasters Tour

    The Loop, Chicago

    • Chronicle the most disastrous, mayhem-filled events the city of Chicago has endured
    • Enjoy a 90 minute, mile-and-a-half-long walk around and through Chicago's Loop
    • Learn of spooky events and sordid tales that plague the streets of Chicago
    • Hear stories of secrets, disasters, victories, and everything in between
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    6 positive reviews
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    River Walk Brunch Tour (Summer)

    (25)
    Ah, brunchy, brunchy, brunch. Is there anything better than waking up, eating some bacon, and sipping on a mimosa? Life doesn't get much better than brunch. With Chicago's Finest Tours, you get it all. First, you'll embark on a Chicago walking tour, listening to captivating tales of the city's both jubilant and tragic past. Imagine the color characters who shaped the city's architecture and history. Once you've built up your appetite, you're headed to Houlihans for a fantastic brunch buffet: eggs, fruit, omelets, bacon, the works. Finish your tour with some storytelling and a calorie-burning walk.
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    River Walk Brunch Tour (Summer)

    111 E Upper Wacker Dr, Chicago

    • Listen to the entertaining stories behind Chicago's history and architecture
    • Indulge in a delicious brunch buffet at Houlihans
    • Relax and learn about Chicago's infamous characters, including the architects, millionaires, and politicians that built this city
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    24 positive reviews
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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.
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    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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    The Pedway Tour

    (6)
    The Pedway is one of Chicago's most misunderstood and enigmatic places. Tour this unique walkway known for connecting some of the city's major buildings. Enjoy a mile of walking, escalators, stairs, and revolving doors filled with ups and downs. You'll learn about everything from architecture to instances of Tiffany glass, while immersing yourself in all the quirky facts and details about the pedway. It's a great way to learn intimate knowledge that even Chicago natives may not know. And, if afterwards you're hungry, stop at one of the seven Dunkin' Donuts The Pedway has to offer!
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    The Pedway Tour

    The Loop, Chicago

    • See the Chicago Pedway while gaining a new perspective of this iconic location
    • Be led by a local, knowledgeable tour guide who knows all the area's ins and outs
    • Enjoy a 90 minute, mile-long walk through this all indoor location that connects many buildings
    • Learn a variety of interesting and quirky facts about this strange urban space
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    6 positive reviews
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    Twilight Riverwalk & History Tour

    (26)
    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!
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    Twilight Riverwalk & History Tour

    1 W Wacker Dr, 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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    26 positive reviews
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    Loop Highlight Tour

    (26)
    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!
    No available dates to book.
    Bucketlist to hear about new dates first!
    Loop Highlight Tour

    1 W Wacker Dr, Chicago

    • Explore Chicago's downtown area known as "The Loop"on this interesting and informative guided walking tour
    • Follow your expert guide through Millennium Park to see the sculpture that everyone calls "The Bean"
    • Marvel at the work of Picasso and Chagall that decorates street corners
    • Learn how "The Second City"rose from the ashes after the Great Fire of 1871
    BOOK NOW ← Back
    26 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.
    No available dates to book.
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    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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