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Top Illinois 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  
US$39.95
From  
US$39.95
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Chicago Prohibition Tour

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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Chicago Style Food Tour

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 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.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$55.00
From  
US$55.00
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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 2-hour 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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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
US$50.00
US$2.50 savings
From  
US$47.50
US$50.00US$2.50 savings
US$50.00
US$2.50 savings
From  
US$47.50
US$50.00US$2.50 savingsSee Details

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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Auditorium Theatre Historic Tour

Get an insider’s look at Chicago’s architectural heritage during this 60-minute 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  
US$12.00
From  
US$12.00
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Haunted Chicago Ghost and Pub Walking Tour

Enjoy a memorable Chicago experience with this haunted pub tour. Your costumed guide, dresses as a Flapper or 1920s Gangster, will lead you on a mile-long, 2.5-hour 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  
US$25.00
From  
US$25.00
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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  
US$70.85
From  
US$70.85
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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
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NEW TO VIATOR

Scenic Chicago North Side Tour and 360 CHICAGO Observation Deck

Discover the sights of North Chicago on a 2-hour group walking tour. Offered in the morning and afternoon, select a start time that fits with your schedule. Follow your guide to Millennium Park, Lake Michigan, and more. Feel free to pause for photos and ask questions whenever you like. You also get free admission to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$51.95
From  
US$51.95
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Chicago History and Architecture Tour

Learn about Chicago's history and architecture and discover the Loop (Chicago's central business district) on this guided, 3-hour walking tour. You'll visit the Pedway, a system of underground tunnels and overhead bridges in the heart of the Windy City that connects over 40 blocks, covering approximately five miles. Learn to navigate these winding passages and hear interesting stories about Chicago’s past, present and future along the way. Also, stroll across the Michigan Avenue Bridge to the newly expanded Chicago Riverwalk and beyond.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$25.00
From  
US$25.00
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Field Museum of Natural History Discovery Pass

Buy your Field Museum Discovery Pass in advance to streamline your sightseeing experience in Chicago. With pass in hand, you'll save time waiting in line and get access to all general admission exhibits, as well as one ticketed special exhibition or a 3D movie. Your pass gives you the ability to explore on your own time, spending as long as you like in the Hall of Gems or checking out the titanosaur. Free tours are available throughout the day.
  • Duration: 1 to 8 hours
  • Free Cancellation
  • Duration: 1 to 8 hours
  • Free Cancellation
From  
US$32.00
From  
US$32.00
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NEW TO VIATOR

Historic Chicago South Side Tour and 360 CHICAGO Observation Deck

Discover the historical sights of South Chicago on a 2-hour group walking tour. Select the morning or afternoon start time, depending on your preference. Follow your guide to Grant Park, Buckingham Fountain, Obama's House, and other sites that define the historical South Side. Pause for photos and ask questions at any time. You also get a free ticket to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$51.95
From  
US$51.95
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NEW TO VIATOR

Scenic Chicago North Side Tour and Chicago Style Pizza

Get a comprehensive overview of Chicago’s North Side on a 3.5-hour sightseeing tour. Home to Wrigley Field, Tribune Tower, and Chicago Water Tower, the vibrant district is not to be missed. Enjoy live narration as you travel along North Lake Shore Drive past Lincoln Park Conservatory and Zoo and much more. After the tour, receive a meal voucher for a personal pizza at the popular Exchequer Restaurant.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$52.95
From  
US$52.95
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Macy's State Street Historical Store Tour

Enjoy a guided, 1-hour, small-group tour of Macy's State Street, a Macy's flagship destination and true American original in Chicago. In and around the National Historic Landmark, see the first-ever restaurant in a department store — the Walnut Room— plus the Tiffany Ceiling, the Great Granite Pillars, the Great Clocks and more. After the tour, receive a 10 percent Visitor Savings Pass to shop and dine through this historic 9-floor building filled with the best in fashion, cuisine and more.
  • Duration: 45 minutes
  • Free Cancellation
  • Duration: 45 minutes
  • Free Cancellation
From  
US$12.00
From  
US$12.00
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NEW TO VIATOR

Historic Chicago South Side Tour with Chicago Style Pizza

See the sights of Chicago's South Side on a tour that takes you south of the Loop along Michigan Avenue and South Lake Shore Drive. Pass by attractions such as the Art Institute of Chicago, Frank Lloyd Wright's Robie House, former President Obama's home, the University of Chicago, Jackson Park, the Museum of Science and Industry, Museum Campus, and Buckingham Fountain. Then head to Exchequer Restaurant and Pub for Chicago-style pizza.
  • Duration: 3 hours 30 minutes
  • Free Cancellation
  • Duration: 3 hours 30 minutes
  • Free Cancellation
From  
US$52.95
From  
US$52.95
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NEW TO VIATOR

Moonlit Cemetery Tour - Bluff City Cemetery

• Join us on an interesting tour of this historic cemetery. Unlike other tours which just talk constantly, you get to enjoy the peace and quiet of the cemetery and anticipate the experiences that await you. • During the tour you will learn some history about the cemetery and different burial practices of the past. We will teach you how to try and capture paranormal activities on your camera, or camera phone. • included in the price is the use of special equipment for detecting Spirits in the cemetery. • This is small-group tour (20 people max) • The tour lasts 3 hours • Your experienced Spirit Guides will take you on a fascinating Moonlit Tour of the Cemetery. • Afterlife Tours, Inc. is giving a percentage of every ticket sold back to the Cemeteries, to assist in the preservation, and reconstruction, of this historic cemetery.
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$50.00
From  
US$50.00
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NEW TO VIATOR

Chicago Walking Tour: A Walk Through Time

Get a comprehensive look at Chicago's architectural history on this unique tour that covers buildings in chronological order. Hear important stories about the city while viewing some of its earliest buildings and new, super-tall high rises.
  • 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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