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Top Chicago Historical & Heritage Tours

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Chicago Crime and Mob Tour

Explore Chicago's gangster past on this 1.5-hour mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
USD39.95
From  
USD39.95
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Chicago Prohibition Adults-Only Tour of Historic Speakeasies

Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
USD45.00
From  
USD45.00
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this 2-hour 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.
  • Duration: 2 hours
  • Duration: 2 hours
From  
USD28.00
From  
USD28.00
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Private Al Capone Gangster Tour in Chicago

Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
USD660.00
From  
USD660.00
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Historic Chicago Walking Bar Tour

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!
  • Duration: 2 hours 30 minutes
  • Duration: 2 hours 30 minutes
From  
USD36.00
From  
USD36.00
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Pizza City USA Pizza Crawl

Immerse yourself in the pizza culture of Chicago with this tour de force of the city's 10 pizza styles. Go beyond deep dish with commentary from your food-loving guide and tastes of four different types over the course of the half-day tour. Learn about some of the most interesting Chicago neighborhoods and their culinary history.
  • Duration: 3 hours
  • Duration: 3 hours
From  
USD49.00
From  
USD49.00
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NEW TO VIATOR

The Original Surf & Turf Tour: A Combination Boat AND Walking Tour!

Our super unique combination of "must see" Chicago sites in one tour — Chicago by boat, by train, and on foot! On this brand new tour route that has been a long-time wish of company founder and award-winning tour guide, Hillary, you will be able to experience Chicago in the best ways possible: by boat on the Chicago River, by “L” from one of Chicago’s fascinating Chinatown neighborhood, and on foot through the center of the city. Inside Chicago Walking Tours calls these new tours “Surf & Turf” tours because you don’t have to worry about choosing a boat tour OR a walking tour: we’re finally giving you both in ONE tour! Come on our newest, most exciting, and most unique tour yet! Let Inside Chicago Walking Tours put their expertise and know-how about the best ways to experience Chicago to use for you, and join us in exploring the best parts of Chicago by boat, by train, and on foot! No need to purchase extra tickets for the boat and train — they’re provided in your ticket price!
  • Duration: 120 to 150 minutes
  • Free Cancellation
  • Duration: 120 to 150 minutes
  • Free Cancellation
From  
USD45.00
From  
USD45.00
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Chicago Walking Tour: Modern Architecture

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.
  • Duration: 1 hour 45 minutes
  • Free Cancellation
  • Duration: 1 hour 45 minutes
  • Free Cancellation
From  
USD26.00
From  
USD26.00
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Field Museum of Natural History All-Access Pass

One of Chicago’s most popular and recognizable landmarks, the Field Museum of Natural History offers a wide array of treasures, from its Hall of Gems to Sue—one of the best-preserved Tyrannosaurus Rex fossils ever found. Guarantee your admission to this in-demand museum, and prevent any stress, by booking your tickets before you travel. Upon arrival, you can explore the museum at your own pace, and even embark on a complimentary, docent-led tour.
  • Duration: 1 to 8 hours
  • Free Cancellation
  • Duration: 1 to 8 hours
  • Free Cancellation
From  
USD38.00
From  
USD38.00
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NEW TO VIATOR

Chicago Theatre Marquee Behind-the-Scenes Tour

Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.
  • Duration: 1 hour
  • Free Cancellation
  • Duration: 1 hour
  • Free Cancellation
From  
USD18.00
From  
USD18.00
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NEW TO VIATOR

Chicago Neighborhoods by L Train and on Foot: Green Line South

Explore Chicago's neighborhoods, culture and history via the elevated train system, with some walking, stories and small bites along the way. This unique Chicago tour begins with an exploration and a bite at one of the city’s newly revitalized spaces: The beautiful Chicago Athletic Association Hotel. Before boarding the train, we’ll visit a few historic and cultural stops in the Loop then make our way to the Cermak-McCormick Place Station.Upon arrival in the Prairie District, we’ll walk to a number of historic sites such as the former Chess Records, the oldest house in the city, the historic Second Presbyterian Church and the Glessner House. To top it off, we’ll finish with some small bites and a drink at Fatpour Tap Works. Following the tour, your guide will be available to assist with directions and your return trip to the Loop.
  • Duration: 4 hours
  • Duration: 4 hours
From  
USD70.00
From  
USD70.00
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Neighborhood Tour of Fulton Market with Food

Spend two hours walking and eating your way through the Fulton food market, Chicago’s new foodie hot spot. Start your tour with a view of the railroad tracks, and get an overview of the area’s history and architecture as you see the former industrial center and its transformation from an edgy underground scene to a culinary destination. Stop to sample locally made deli meat, pickles, beer, and a classic submarine sandwich as you explore.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
USD42.00
From  
USD42.00
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Chicago Walking Tour: Art Deco Skyscrapers

Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
USD26.00
From  
USD26.00
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NEW TO VIATOR

The Chicago Tour

This tour is an overview of some of Chicago's most fascinating neighborhoods, history, architecture, and foods. We will take you beyond the downtown loop to explore some of the great neighborhoods that make up this amazing and diverse city. Did you know that Chicago is home to 77 distinct neighborhoods? Each one has their own personality and vibe that make it worth exploring. The Chicago Tour will help you see the city without worrying about the logistics or the effort of planning and will explore the Loop, Chinatown, Pilsen, and the West Loop. Be prepared to walk a lot as we will explore by foot and use the city public transportation to connect us to each neighborhood. Together we will see the city by going off the beaten path for a more authentic experience. Each tour will include all food and drinks (listed in itinerary below) and an unlimited public transit day pass. So, after the tour wraps up, you have the ability to go back and explore more of the city!
  • Duration: 4 hours
  • Duration: 4 hours
From  
USD99.00
From  
USD99.00
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NEW TO VIATOR

The Entrepreneurs of Chicago

Learn about the entrepreneurs who built Chicago on this walking tour. We'll see the locations around the Loop where these titans of industry made their mark, turning what was once a small military outpost into one of the most innovative cities of the century. Focusing on the entrepreneurs during the time between Chicago becoming a city (1833) to the World's Fair (1893), you'll hear some names you recognize, and possibly some you don't. During this 90 minute tour, you'll get to know several of Chicago's greatest entrepreneurs:What were their backgrounds? What were their struggles? What strategies did they use to beat the competition? How did they build their empires? And what advice would they give?Get ready to walk ~2.5 miles of Chicago's downtown streets where you will see exactly where these 19th-century industrialists built their fortunes.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
USD30.00
From  
USD30.00
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Chicago's Best History and Riverwalk Tour

Discover the true story of Chicago’s history and learn how this once-swampland became one of the biggest and most-popular cities in the world on this 2.5-hour walking tour. Hear stories about the Windy City’s past — from the Fort Dearborn Massacre to the Great Chicago Fire, the 1893 World’s Fair and much more. Stroll the streets, across the Michigan Avenue Bridge to the Chicago Riverwalk and beyond. Also included: a personal, pictorial view book to compare the city’s past with the present plus a headset to hear the guide clearly.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
USD25.00
From  
USD25.00
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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
USD30.00
From  
USD30.00
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Auditorium Theatre Historic Tour

Get an insider’s look at Chicago’s architectural heritage during this tour of Auditorium Theatre, a National Historic Landmark. Learn about the history of this 126-year old performance venue as you gaze in awe at the 24-karat gold-leafed ceiling arches, intricate wall mosaics, and painstakingly-restored stencil patterns. You’ll also learn about the numerous concerts, plays, operas, political conventions, and more that have graced its stage.
  • Duration: 1 hour
  • Free Cancellation
  • Duration: 1 hour
  • Free Cancellation
From  
USD12.00
From  
USD12.00
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Haunted Chicago Segway Tour

Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide for 2 hours as they show you the sites of some of the most gruesome murders and disasters in Chicago's colorful history. See Chicago's iconic landmarks lit up during the spookiest time of year and hear about the mysterious, haunted history of this storied city.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
USD70.85
From  
USD70.85
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Chicago Crime and Pizza Walk

Explore the River North and Gold Coast neighborhoods in Chicago during a 2-hour walking that focuses on the city's famous deep-dish pizza and most notorious criminals.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
USD47.50
From  
USD47.50
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Haunted Chicago Ghost and Pub Walking Tour

Enjoy a memorable Chicago experience on this haunted pub tour. Your costumed guide, dressed as a Flapper or 1920s Gangster, will lead you on a mile-long journey while telling spooky stories of forgotten cemeteries, lingering spirits, and more. Stop at three different bars for drinks (at own expense) as you learn the secret tales behind Chicago’s haunted past.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
USD25.00
From  
USD25.00
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The Original 1893 Chicago World's Fair Food Tour

Travel back in time to the original 1893 World’s Fair in Chicago for this guided, 3.5-hour food tour. Led by Chicago’s ‘Gold Coast Queen,’ Bertha Palmer, hear her favorite memories from the great 1893 Columbian Exposition and enjoy five different food tastings from around the Windy City.
  • Duration: 3 hours
  • Duration: 3 hours
From  
USD78.00
From  
USD78.00
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Chicago Segway Art and Architectural Tour

Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
USD70.40
From  
USD70.40
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Old Polonia and Wicker Park History and Food Tour

Explore the past and present of two Chicago neighborhoods on this guided, 2.5-hour walking tour. Visit Wicker Park, once infamous as a home for gang bangers, drug addicts and prostitutes, it’s now widely considered one of the trendiest neighborhoods in America. Then walk through the West Town district of Noble Square, formerly known as ‘Old Polonia.’ Along the way, see many popular points of interest and enjoy food tastings at some of the area’s best eateries.
  • Duration: 2 hours 30 minutes
  • Duration: 2 hours 30 minutes
From  
USD45.00
From  
USD45.00
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(888) 651-9785
(888) 651-9785