Walking Tours · This Weekend

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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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    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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    Lincoln Park and Gangster Tour

    (17)
    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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    17 positive reviews
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    Interiors of the Loop Tour

    You've never seen Chicago like this before. Inside Chicago Walking Tours has scoured this buzzing business district and carefully selected a handful of must-see hidden treasures, just for you! On this walking tour, you'll be amazed at the magnificence beyond the facade. All those buildings you pass by when you're rushing through downtown Chicago -- have you ever thought about what's behind those doors? An entire world exists that people rarely think about, let alone have a chance to see. Inside Chicago Walking Tours has scoured the city's buzzing business district and carefully selected a handful of must-see treasure that are usually hidden behind closed doors! On this walking tour, you'll be amazed at the magnificence beyond the facades. Your knowledgeable, trusty tour guide will lead you away from the hustle and bustle of downtown Chicago for a beautiful adventure through the most stunning interior spaces you'll ever see! Sites include rooms full of colorful stained glass mosaics, art deco lobbies straight out of the roaring 20s, 80-foot ceilings covered in real gold, and much more! So what're you waiting for? Let Inside Chicago Walking Tours show you this "second side" of the Second City!
    Interiors of the Loop Tour

    425 S. Financial Place, Chicago

    • Experience an enchanting world that lies behind the doors of many buildings that most people unknowingly pass by every day
    • Allow your friendly, knowledgeable guide to show you the best of Chicago's interiors during this 1-and-a-half-hour tour
    • See art deco lobbies that look straight out of the roaring 20's, chandeliers imported from France, and more!
    • Take a break from the hustle and bustle of downtown Chicago to go on a beautiful adventure
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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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    Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs Tour

    (7)
    Experience Chicago on a walking and food tour of the central business district. Visits to legendary sites such as Palmer House Hotel, Marshall Field's Building, and Millennium Park are punctuated by stops in local food joints for samples of Chicago's favorite bites. Your expert guide shares the history of Chicago's most iconic buildings and foods as you walk around the Windy City's legendary downtown Loop. Follow your knowledgeable guide through downtown Chicago and visit a number of stunning indoor spaces including the historic Palmer House Hotel, the Walnut Room and Macy's. Your guide also takes you to various spots for samples of some of Chicago's favorite foods such as pizza, hot dogs, brownies, and beer from a local brewery.
    Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs Tour

    540 N Lake Shore Dr, Chicago

    • Experience Chicago's vibrant food scene on a walking tour of the central business district
    • Visit legendary sites such as Palmer House Hotel, Marshall Field's Building, and Millennium Park
    • Enjoy stops in various local food joints for samples of Chicago's favorite bites
    • Hear about the history of Chicago's most iconic buildings and foods from an expert local guide
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    7 positive reviews
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    Headlines/History Running Tour

    (23)
    So you've always heard about the Great Chicago Fire, but don't really know when it happened or much else about it. This tour is the perfect chance to put it into context and learn about other significant events that helped shape Chicago. Going back more than 200 years, visit 5 sites of tragic disasters that made headlines around the country and the world. On this tour with CRTC, you'll pass famous landmarks and incredible architecture while learning history of these disasters. See places like the historic Palmer House Hotel, Fort Dearborn, the Monadnock Building and more. This is a great way to see Chicago, learn about its history, and get a great workout at the same time! You're about to go hard. ChicaGO hard.
    Headlines/History Running Tour

    Central Loop, Chicago

    • Visit the sites of five tragic disasters in Chicago that made headlines across the world
    • See the the historic Palmer House Hotel, Fort Dearborn, and more
    • Enjoy learning from your knowledgeable guide about events that shaped the city
    • Get a great workout while discovering a whole new side of Chicago
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    23 positive reviews
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    Burnham Plan Running Tour

    (1)
    "Make no little plans," wrote Daniel Burnham. What followed was an ambitious undertaking that would become a blueprint for city-planning the world over. On this tour with CRTC, you'll travel across the beautiful Chicago River and run along the Magnificent Mile. You'll also visit Chicago's #1 tourist attraction, the historic Navy Pier. Come and see the Burnham Plan in action today and learn the amazing history of Chicago's development at the beginning of the 20th Century. You're about to go hard. ChicaGO hard.
    Burnham Plan Running Tour

    2044 W Fletcher St, Chicago

    • Discover the amazing history of Chicago's development that began at the turn of the 20th century
    • Learn about the Daniel Burnham, the famous architect and urban planner
    • Run along the Magnificent Mile and see Chicago's #1 tourist destination, the historic Navy Pier
    • Get a great workout while discovering a whole new side of Chicago
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    1 positive reviews

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