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Top Chicago Historical & Heritage Tours

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

Chicago Crime and Mob Tour

Explore Chicago's gangster past on this 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  
US$39,95
From  
US$39,95
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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  
US$45,00
From  
US$45,00
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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  
US$28,00
From  
US$28,00
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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  
US$660,00
From  
US$660,00
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Explore Chicago's notorious mob and gangster past aboard a luxury bus

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are: the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is educational but also very entertaining because our Gangster Guides are actors. Our Untouchable Tour Gangster Guides take on the persona of a gangster and have fun with it. Reservations are strongly recommended.
  • Duration: 1 hour 45 minutes
  • Duration: 1 hour 45 minutes
From  
US$39,00
From  
US$39,00
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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  
US$99,00
From  
US$99,00
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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  
US$47,50
From  
US$47,50
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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  
US$38,00
From  
US$38,00
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Chicago Lakeside Architecture Tour

Get views of Chicago's famous architecture from the deck of a boat during this sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
  • Duration: 1 hour 15 minutes
  • Duration: 1 hour 15 minutes
From  
US$37,00
From  
US$37,00
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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  
US$36,00
From  
US$36,00
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Chicago Deluxe Motor Coach Tour

This is a very thorough and relaxing city highlights tour! We pick up at three downtown hotels before beginning our adventure at 875 N. Michigan, the former John Hancock Center. We’ll have a photo-stop at the home of the Cubs, the legendary Wrigley Field. We’ll then take Lake Shore Drive to the home of the Bears, the historic Soldier Field. We’ll make a photo-stop at the Museum Campus for the best view of the lake and skyline. Passing by the White Sox stadium, your driver and tour guide will take you through Chinatown, Greektown, and other fun areas. We’ll show you the architectural masterpieces of the Loop on the way to our origin at the top of the Magnificent Mile and the destination hotels.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$55,00
From  
US$55,00
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Chicago in a Day: Food, History and Architecture Combo Tour

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!Marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the worldGet around The Loop like a local: at street level, underground, elevated rails or perhaps even on the waterEnjoy a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolateGet a taste for Chicago’s most famous food in one of the city’s most historic neighborhoodsDiscover why locals have so much passion for their Chicago-style classics
  • Duration: 5 hours
  • Free Cancellation
  • Duration: 5 hours
  • Free Cancellation
From  
US$99,00
From  
US$99,00
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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  
US$18,00
From  
US$18,00
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Lincoln Park Hauntings Ghost Investigation Tour

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator. Like Ursula, all of our guides are all real investigators and true Chicagoans. We love investigating, we love Chicago history, and we would love to show you Chicago's haunted history. This is the only tour which takes you out of the downtown area and into one of the most haunted parts of Chicago: Lincoln Park, the old City Cemetery, which was ravaged by the Great Fire of 1871, leaving 10,000 graves behind. The bodies are all still here, as well as the ghosts. The tour also visits the site of the St. Valentine's Day Massacre and the site of Suicide Bridge, where more than 100 desperate souls lost their lives.
  • Duration: 2 hours 15 minutes
  • Free Cancellation
  • Duration: 2 hours 15 minutes
  • Free Cancellation
From  
US$27,00
From  
US$27,00
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Chicago: Historical Food Tour of River North

Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spots for some of the city’s best loved dishes. From deep dish pizza to Chicago-style hot dogs, this tour will leave you filled with delicious local foods as well as some insider knowledge into the city’s culinary history and culture.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$59,00
From  
US$59,00
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Pizza City USA Pizza Coach Tour

Take a deep dive into the deep dish and beyond with this pizza tour of Chicago. On a comfortable tour bus, run around town tasting four different pizza styles and learning about their differences. Meet some chefs and owners and learn about how the pizzas are made and Chicago's pizza history. You won't leave hungry.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$69,00
From  
US$69,00
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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  
US$26,00
From  
US$26,00
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Learn The Lost Language of Buildings

This tour will teach you how to look at buildings in a whole different way. It will quite literally change the way you see the world around you. Forever. I promise. Architecture is called "the mother of all arts," it's ornament and design is intended to make you feel something, just like any great piece of art. By studying symbols and gargoyles, faces, demons, and design choices, on buildings that range from historic to the most modern of modern skyscrapers, we'll learn the lost language of buildings. By learning to "look up" and study buildings by studying their parts, we'll learn more about the world around us, about our past and about our future.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$30,00
From  
US$30,00
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Land and River Architecture Tour of Chicago's Scenic North Side

Discover Chicago’s iconic architectural gems from every angle on a 3.5-hour tour of the North Side. Divided between land and water, the comprehensive tour enables you to cover a huge area of the city without getting worn out. Travel comfortably by coach or trolley to Fort Dearborn, Wrigley Building, and more. Afterwards, see the Windy City's famous skyscrapers, bridges, and historical sites on a 90-minute cruise down Chicago River.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$73,95
From  
US$73,95
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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  
US$26,00
From  
US$26,00
See Details

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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  
US$45,00
From  
US$45,00
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Chicago Walking Tour: A Walk Through Time

Travel through architectural history on this walking tour that covers Chicago's most famous buildings in chronological order. With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth guided commentary on Chicago's architectural history; you'll learn about each building and its importance in the architectural canon.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$26,00
From  
US$26,00
See Details

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  
US$30,00
From  
US$30,00
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Train and Walking Tour: 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  
US$65,00
From  
US$65,00
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(888) 651-9785
(888) 651-9785