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Top Chicago Walking Tours

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70 Chicago Walking Tours

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You can reserve your spot today and pay when you're ready.Learn more

Loop Interior Architecture Walking Tour with PedwayArchitecture Tours

Loop Interior Architecture Walking Tour with Pedway

star-5
Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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Booked by 2,657 travellers
  • 2 hours
From  
US$29.00 
From  
US$29.00 
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  • 2 hours

Historic Chicago Walking Bar TourArchitecture Tours

Historic Chicago Walking Bar Tour

star-4.5
Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide’s stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour – great for visitors and locals alike!
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Booked by 740 travellers
  • 2 hours 30 minutes
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  • Free Cancellation
From  
US$39.00 
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US$39.00 
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  • 2 hours 30 minutes
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  • Free Cancellation

Discover Chicago's Underground City - all indoor walking tourCultural Tours

Discover Chicago's Underground City - all indoor walking tour

star-4.5
Discover a lesser-known side of the Windy City on this Chicago Pedway tour, a walking excursion through the many heated passageways, tunnels, and corridors that link some of the town's most iconic buildings. Follow your humorous guide on an insider's exploration of these relatively unknown walkways, learning about the area's architecture and history as you go. It's a great way to explore a different side of Chicago unknown to most visitors.
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Booked by 869 travellers
  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$24.95 
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  • 1 hour 30 minutes
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  • Free Cancellation

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Gangsters and Ghosts Tour in ChicagoCultural Tours

Gangsters and Ghosts Tour in Chicago

star-4.5
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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Booked by 7,757 travellers
  • 2 hours
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  • Free Cancellation
From  
US$27.00 
From  
US$27.00 
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  • 2 hours
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  • Free Cancellation

Go Chicago Explorer Pass with SkyDeck and 360 ChicagoMulti-day Tours

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 42 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 3, 4, or 5 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: You can enjoy the extra flexibility in case your travel plans need to change—all passes are valid for one year from purchase date and only become activated with your first attraction visit. After activation, your pass will be valid for 30 days and/or the remaining number of attraction choices purchased.
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Booked by 5,231 travellers
  • 30 days
From  
US$66.00 
From  
US$66.00 
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  • 30 days

Chicago World's Fair of 1893 Walking TourHistorical & Heritage Tours

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Chicago World's Fair of 1893 Walking Tour

star-5
Discover the lasting influence of the 1893 World’s Fair in Chicago on a tour of downtown. See the historic Auditorium Building, the Chicago Athletic Association Hotel and other examples of Chicago’s fine architecture. Your guide provides informative commentary and entertaining games during your Chicago walking tour, which mostly takes place indoors, making it ideal for all seasons.
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Booked by 134 travellers
  • 2 hours 45 minutes
From  
US$39.00 
From  
US$39.00 
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  • 2 hours 45 minutes

Chicago's Chinatown Food and Walking TourHalf-day Tours

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Chicago's Chinatown Food and Walking Tour

star-4.5
Explore Chicago's Chinese food scene on this walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. Enjoy included tastings from restaurants and other food venues in Chinatown—a great way to start a night out in the city.
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Booked by 92 travellers
  • 3 hours
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  • Free Cancellation
From  
US$62.99 
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  • 3 hours
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  • Free Cancellation

Best in Chow: Chicago River North Food TourWalking Tours

Best in Chow: Chicago River North Food Tour

star-5
Go beyond deep-dish on this culinary walking tour of Chicago, which includes five tastings of classic Windy City cuisine. Navigate the endless options of downtown dining with a guide who can provide insight into the best food Chicago has to offer, and skip the lines and the wait with VIP access to popular restaurants.
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Booked by 341 travellers
  • 2 hours 30 minutes to 3 hours
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  • Free Cancellation
From  
US$64.00 
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US$64.00 
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  • 2 hours 30 minutes to 3 hours
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  • Free Cancellation

Windy City Ghost TourHistorical & Heritage Tours

Windy City Ghost Tour

star-5
Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.
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Booked by 30 travellers
  • 1 hour
From  
US$21.32 
From  
US$21.32 
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  • 1 hour

Underground Donut Tour - Wicker Park EditionWalking Tours

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Underground Donut Tour - Wicker Park Edition

star-5
Wicker Park is one of Chicago’s coolest and most food-oriented neighborhoods—and on this one-of-a-kind walking tour, you’ll see the sights while seeking out the best donuts that the area has to offer. Meet your guide in the morning in Wicker Park, and set out on foot. You'll visit four popular cafes and bakeries, will sample numerous creative donut flavors, and will learn more about the neighborhood. Additional drinks and treats are also available for purchase, if you wish.
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Booked by 45 travellers
  • 2 hours
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  • Free Cancellation
From  
US$35.00 
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US$35.00 
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  • 2 hours
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  • Free Cancellation

Famous Tastes of Chicago Food TourHalf-day Tours

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Famous Tastes of Chicago Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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Booked by 2,098 travellers
  • 3 hours
From  
US$68.50 
From  
US$68.50 
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  • 3 hours

Small-Group Chicago Food Tour: Gold Coast and Old TownHalf-day Tours

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Small-Group Chicago Food Tour: Gold Coast and Old Town

star-5
Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.
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Booked by 980 travellers
  • 3 hours
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  • Free Cancellation
From  
US$74.67 
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  • 3 hours
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  • Free Cancellation

Chicago Favorites Ultimate Food & Walking TourBeer & Brewery Tours

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Chicago Favorites Ultimate Food & Walking Tour

star-5
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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Booked by 1,078 travellers
  • 2 hours 30 minutes
From  
US$62.99 
From  
US$62.99 
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  • 2 hours 30 minutes

Chicago Loop Secret Food TourHalf-day Tours

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Chicago Loop Secret Food Tour

star-5
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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Booked by 592 travellers
  • 3 hours
From  
US$81.48 
From  
US$81.48 
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  • 3 hours

Chicago Style Food TourHalf-day Tours

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Chicago Style Food Tour

star-4.5
Discover Chicago’s food, history, architecture and culture on this small-group walking tour. Try the Windy City’s quintessential staples from local restaurants and specialty food shops like Downtown Dogs and the world-famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog, and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural, and architectural components that make up this legendary town.
...  More
Booked by 803 travellers
  • 3 hours
From  
US$71.47 
From  
US$71.47 
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  • 3 hours

Chicago Comedy and Craft Beer Walking TourBeer & Brewery Tours

Chicago Comedy and Craft Beer Walking Tour

star-4
Discover the best of Chicago’s local brews and comedic history on a 2.5-hour craft beer tour. Follow your guide to Old Town bars, including Old Town Ale House and Burton Place.  Taste a wide range of locally produced beers, along with a free snack. Along the way, learn all about Chicago’s historical and thriving comedy scene with stops by Second City and Zanies.
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Booked by 15 travellers
  • 2 hours 30 minutes
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  • Free Cancellation
From  
US$62.99 
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  • 2 hours 30 minutes
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  • Free Cancellation

Chicago Walking Tour: Modern ArchitectureArchitecture Tours

Chicago Walking Tour: Modern Architecture

star-4.5
Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
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Booked by 190 travellers
  • 1 hour 45 minutes
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  • Free Cancellation
From  
US$26.00 
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US$26.00 
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  • 1 hour 45 minutes
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  • Free Cancellation

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMapPrivate Sightseeing Tours

Hidden History in Chicago's Gold Coast Walking Audio Tour by VoiceMap

star-4
Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating guided tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood. The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.
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Booked by 18 travellers
  • 50 minutes
From  
US$5.34 
From  
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  • 50 minutes

Chicago Architecture Walking Tour: Dazzling Interiors of the LoopLuxury Tours

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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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Booked by 335 travellers
  • 2 hours
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  • Free Cancellation
From  
US$30.00 
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US$30.00 
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  • 2 hours
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  • Free Cancellation

Train and Walking Tour - Prairie District: Street of the EliteHalf-day Tours

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Train and Walking Tour - Prairie District: Street of the Elite

star-5
Step off the typical tourist trail, and discover one of Chicago’s oldest and most scenic neighborhoods, on this walking tour of the Prairie District. Meet your guide in the morning at the Chicago Athletic Association, and set off with just a small group for company. The Prairie District is just a short L ride away; you can look forward to seeing the Second Presbyterian Church, Glessner House, Motor Row, and otherwise discovering how Chicagoans lived at the turn of the 20th century.
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  • 4 hours
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  • Free Cancellation
From  
US$81.60 
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  • 4 hours
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  • Free Cancellation

Chicago Architecture Crash Course Walking TourArchitecture Tours

Chicago Architecture Crash Course Walking Tour

star-5
See Chicago from a new perspective with this art- and pop culture-themed architectural walking tour. Follow an informative guide through the city’s streets, from the Michigan Avenue Bridge to the new Maggie Daley Park, while learning about the city’s history, architecture, and the fascinating connections between art history and Chicago architectural styles. Enrich your understanding of this beautiful American city with this fun and affordable outing.
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Booked by 14 travellers
  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$25.00 
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US$25.00 
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  • 1 hour 30 minutes
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  • Free Cancellation

Small-Group Chicago Food Tour: ChinatownHalf-day Tours

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Small-Group Chicago Food Tour: Chinatown

star-5
Sample different styles and varieties of Chinese food during this gourmet walking tour of Chicago's Chinatown. Follow your local food-loving guide through one of the oldest Chinese neighborhoods in the country to taste several Chinese regional delicacies. The price of this small-group tour, limited to 12 people, includes tastings at restaurants; enough food to add up to a full lunch.
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Booked by 149 travellers
  • 3 hours
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  • Free Cancellation
From  
US$80.00 
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  • 3 hours
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  • Free Cancellation

Chicago Architecture TourArchitecture Tours

Chicago Architecture Tour

Surround yourself in the Windy City's architectural gems on a 2-hour walking tour. Follow your guide past noteworthy landmarks and lesser known gems. Then visit the Chicago Cultural Center, also known as The People’s Palace, and marvel at the Randolph Street entrance, Grand Army of the Republic Memorial, and more. Beginning at the Clark Street Bridge, the tour concludes next to Millennium Park where you can continue your day of sightseeing.
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Booked by 9 travellers
  • 2 hours
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  • Free Cancellation
From  
US$25.00 
From  
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  • 2 hours
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  • Free Cancellation

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMapPrivate Sightseeing Tours

Discovering Vintage Chicago: The Loop Walking Audio Tour by VoiceMap

star-1
Take a walk back in time through the history of Chicago's Loop on this app-enabled tour. After downloading the app and tour to you smartphone, you and your party will listen to author Amy Bizzarri, an author and expert in Chicago history, as she leads you through walking tour of the city. The GPS-enabled tour will trigger commentary at just the right times, and you can stop and start whenever you like for a flexible experience that lets you move at your own pace. Highlights include Daley Plaza, the Chicago Theater, Berghoff Restaurant, and the Art Institute of Chicago.
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Booked by 11 travellers
  • 50 minutes
From  
US$5.34 
From  
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  • 50 minutes


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