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Top Chicago Historical & Heritage Tours

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60 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

SPECIAL OFFER

Chicago Crime and Mob Tour

star-4
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
US$35.95
US$39.95
US$4.00 savings
From  
US$35.95
US$39.95
US$4.00 savings
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  • 1 hour 30 minutes
  • Free Cancellation

Chicago Prohibition Tour

Chicago Prohibition Tour

star-4.5
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.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
US$45.00
From  
US$45.00
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  • 3 hours 30 minutes
  • Free Cancellation

Chicago in a Day: Food, History and Architecture Combo Tour

Chicago in a Day: Food, History and Architecture Combo Tour

star-5
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
From  
US$99.00
From  
US$99.00
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  • 5 hours
  • Free Cancellation

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

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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  • 2 hours
From  
US$28.00
From  
US$28.00
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  • 2 hours

Private Speakeasy Pub Crawl in Chicago with Local Historian

Private Speakeasy Pub Crawl in Chicago with Local Historian

Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.
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  • 3 hours
  • Free Cancellation
From  
US$660.00
From  
US$660.00
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  • 3 hours
  • Free Cancellation

Chicago Theatre Marquee Behind-the-Scenes Tour

Chicago Theatre Marquee Behind-the-Scenes Tour

star-4
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.
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  • 1 hour
  • Free Cancellation
From  
US$18.00
From  
US$18.00
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  • 1 hour
  • Free Cancellation

Chicago Private 15 Minute Helicopter Tour For Two

Chicago Private 15 Minute Helicopter Tour For Two

star-5
Get an overview of Chicago's famous skyline in just 15 minutes on this private helicopter flight. There's no better or faster way to take in the city's world-class architecture. You'll get unobstructed aerial views and guaranteed window seats on this private helicopter flight, which makes it easy to take photos. Your pilot/guide will provide insightful commentary as you fly.
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  • 15 minutes
  • Free Cancellation
From  
US$520.00
From  
US$520.00
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  • 15 minutes
  • Free Cancellation

Chicago Night Crimes Tour

Chicago Night Crimes Tour

star-4.5
Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
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  • 120 to 150 minutes
  • Free Cancellation
From  
US$45.00
From  
US$45.00
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  • 120 to 150 minutes
  • Free Cancellation

Historic Chicago Walking Bar Tour

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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  • 2 hours 30 minutes
From  
US$38.00
From  
US$38.00
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  • 2 hours 30 minutes

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
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.
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  • 3 hours
  • Free Cancellation
From  
US$660.00
From  
US$660.00
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  • 3 hours
  • Free Cancellation

Sin and Suds Beer Tour in the Loop and South Loop

Sin and Suds Beer Tour in the Loop and South Loop

star-5
Explore Chicago’s Loop and South Loop neighborhoods — and get a taste of some local beverages — on this guided, 3-hour beer tour. Visit popular downtown establishments, sample some of the city’s finest brews and learn how beer goes with Chicago’s criminal past, discovering the basics of the Windy City’s vice history. From Al Capone and the local mob scene to the infamous Sands, the toughest criminal district in the city — this tour creates a unique experience that is both fun and memorable. Beer tastings plus a pizza pairing at one location included.
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  • 3 hours
  • Free Cancellation
From  
US$73.70
From  
US$73.70
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  • 3 hours
  • Free Cancellation

Crime and Haunted Tour in Chicago

SPECIAL OFFER

Crime and Haunted Tour in Chicago

star-5
Haunted places and gangster hangouts, hidden history and crime scenes. Walking tour with a Secret route, we take you where no one else can. This isn’t just another boring tour — it is an adventure where you travel back in time as a gangster member. Prohibition Era, Speakeasies, Death Alley and Congress hotel part of our route. You will hear untold stories and outlandish details. Come discover the hidden.
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  • 1 hour 45 minutes
  • Free Cancellation
From  
US$25.81
US$29.00
US$3.19 savings
From  
US$25.81
US$29.00
US$3.19 savings
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  • 1 hour 45 minutes
  • Free Cancellation

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

star-5
The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
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  • 2 hours 30 minutes
  • Free Cancellation
From  
US$49.00
From  
US$49.00
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  • 2 hours 30 minutes
  • Free Cancellation

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

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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  • 2 hours
  • Free Cancellation
From  
US$30.00
From  
US$30.00
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  • 2 hours
  • Free Cancellation

Bacon and Brews Beer Tour in Lakeview and Lincoln Park

Bacon and Brews Beer Tour in Lakeview and Lincoln Park

star-4.5
Sip your way through Lakeview and Lincoln Park’s best beers on a 3-hour walking tour of these iconic Chicago neighborhoods. Follow your guide to a series of bars and breweries for flights of regional craft brews, and raise a glass as you learn how Chicago’s immigrant cultures created a proud brewing tradition. Experience the bar scene like a local, try a classic Midwestern pairing at a beer-and-bacon bar, and see what’s on draft in the Windy City.
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  • 3 hours
From  
US$67.00
From  
US$67.00
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  • 3 hours

Chicago: Historical Food Tour of River North

Chicago: Historical Food Tour of River North

star-5
Get to know the food offerings in River North on this small-group walking tour. As you explore, listen to in-depth commentary from your guide on the culinary history of Chicago and the culture of the River North neighborhood. With a small group of just 12 fellow food-lovers, you'll enjoy personalized attention and the chance to chat about your favorite tastings. Samples include the classic Italian beef, a Chicago-style hot dog, and the famous deep dish pizza.
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  • 2 hours
  • Free Cancellation
From  
US$59.00
From  
US$59.00
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  • 2 hours
  • Free Cancellation

Land and River Architecture Tour of Chicago's Scenic North Side

Land and River Architecture Tour of Chicago's Scenic North Side

star-4.5
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.
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  • 3 hours 30 minutes
  • Free Cancellation
From  
US$76.95
From  
US$76.95
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  • 3 hours 30 minutes
  • Free Cancellation

Chicago Walking Tour: Art Deco Skyscrapers

Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From  
US$28.60
From  
US$28.60
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  • 1 hour 30 minutes
  • Free Cancellation

Windy City Ghost Tour

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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  • 1 hour
  • Free Cancellation
From  
US$19.99
From  
US$19.99
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  • 1 hour
  • Free Cancellation

Auditorium Theatre Historic Tour

Auditorium Theatre Historic Tour

star-5
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.
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  • 1 hour
  • Free Cancellation
From  
US$12.00
From  
US$12.00
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  • 1 hour
  • Free Cancellation

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

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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  • 50 minutes
From  
US$5.00
From  
US$5.00
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  • 50 minutes

Chicago Riverwalk & History Tour - Self-Guided Walking Tour (iPhone & Android)

SPECIAL OFFER

Chicago Riverwalk & History Tour - Self-Guided Walking Tour (iPhone & Android)

Explore Chicago's Riverwalk, from Lake Michigan to Franklin Street, with this downloadable GPS-enabled tour. Independent travelers who don't want to join a traditional tour group will appreciate the freedom that following this app-based tour provides. Walk at your own pace and learn about sights such as the Chicago River Museum, the McCormick Bridgehouse, the Vietnam Veterans Memorial Plaza, and others.
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  • 1 to 2 hours
From  
US$2.50
US$5.00
US$2.50 savings
From  
US$2.50
US$5.00
US$2.50 savings
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  • 1 to 2 hours

Lakefront and Museum Campus Segway Tour

Lakefront and Museum Campus Segway Tour

star-5
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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  • 2 hours 30 minutes
  • Free Cancellation
From  
US$74.12
From  
US$74.12
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  • 2 hours 30 minutes
  • Free Cancellation

Chicago Private 30 Minute Tour For Two

Chicago Private 30 Minute Tour For Two

Fly high over Chicago's skyline in a helicopter for thirty minutes with a special someone on this private flight. This tour is perfect for special occasions or those who are short on time in Chicago; it's the fastest way to see it all. Ask questions of your pilot/guide and listen to guided commentary as you take in the amazing aerial views.
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  • 30 minutes
  • Free Cancellation
From  
US$770.00
From  
US$770.00
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  • 30 minutes
  • Free Cancellation


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