Walking Tours · Tomorrow

(9 activities)
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    Historic Chicago Bar Tour

    (16)
    On this pub crawl with an educational twist, you'll explore Chicago's entertainment history and learn about prohibition, jazz, vices, and social clubs. You will interact with historic photos and videos on shared iPads and visit historic buildings for three drink stops. On this walking tour of Chicago, visit some magnificent lobbies and really engage with beautiful historic architecture. Historic photos and video clips are presented on shared iPads along with expert tour guide commentary.
    Historic Chicago Bar Tour

    435 N Michigan Ave, Chicago

    • Join a historic pub crawl with an educational twist as you enjoy delicious beverages
    • Explore Chicago's entertainment history and observe storied architecture
    • Learn about local prohibition, jazz, theater, vices, and social clubs
    • Interact with Chicago in one of the most unique ways imaginable
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    16 positive reviews
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    Amazing Scavenger Hunt Adventure (Chicago)

    (6)
    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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    6 positive reviews
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    Interior Architecture Loop Tour

    (13)
    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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    13 positive reviews
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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

    The Loop, 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 Disasters Tour

    (8)
    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!
    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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    8 positive reviews
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    The Pedway Tour

    (8)
    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!
    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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    8 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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    Sports History and Landmark Tour

    (1)
    See the homes of Chicago's iconic sports teams as you are escorted in a comfortable van to the city's top sports parks, learning the history of each during your journey. Begin by visiting the home of the Chicago Cubs--Wrigley Field. Originally built in 1914 as Weeghman Park for the Chicago Federal League baseball team, the Chicago Whales, the stadium name was changed when chewing-gum titan William Wrigley Jr. purchased the team in 1921. Next, stop at the United Center, home of the Chicago Bulls basketball team and Blackhawks hockey team, to see the bronze Michael Jordan statue, officially known as The Spirit. A tourist favorite, the statue was created shortly after Jordan's retirement to commemorate his 3-consecutive NBA championships as a Chicago Bull. Your next destination is the oldest NFL stadium, Soldier Field. This lakefront field is home to the Chicago Bears.
    Sports History and Landmark Tour

    Hotel pickup, Chicago

    • If you are a sports fanatic, this tour is for you!
    • This tour shuttle you and your friends to the top sports parks in Chicago for the ultimate photo op
    • You will visit Chicago's historic Wrigley Field - built in 1914, the United Center - home of the Chicago Bulls and Blackhawks
    • End the tour at the Harry Caray's Water Tower with admission to the Chicago Sports Museum!
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    0 positive reviews
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    Grant Park 5K Running Tour

    (10)
    Do you know all the hidden gems that are hiding in Chicago's Grant Park? There is more to see then just the Buckingham Fountain. This Grant Park 5K run will show you some of the secret spots that other runners miss. You'll also visit the more popular areas and enjoy some of the best loved trails. As you run, your professional guide will share stories about the park's history that will amaze you. The park has been home to a post office, armory and baseball club during its tumultuous history. Today, it is a beautiful green space for Chicagoans.
    Grant Park 5K Running Tour

    205 E Randolph St, Chicago

    • Discover Grant Park's hidden gems on a running tour
    • See popular and hidden sites with the help of a guide
    • Learn surprising historical facts about Grant Park
    • Enjoy incredible views and peaceful scenery
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    10 positive reviews

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