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Top Chicago Pop Culture

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17 results | All Chicago Tours

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Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1169
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

Windy City Ghost Tour

Windy City Ghost Tour

star-5
6
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
  • Taking safety measures
From
$24.09
From
$24.09
Taking safety measures

Haunted Chicago Ghost and Pub Walking Tour

Haunted Chicago Ghost and Pub Walking Tour

star-4.5
8
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.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$31.50
From
$31.50
Taking safety measures

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2-Hour Haunted Segway Tour of Chicago

2-Hour Haunted Segway Tour of Chicago

star-4.5
22
Glide through the city of Chicago by moonlight on this haunted Segway tour. Follow your costumed local guide 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.
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4
737
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
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Private Al Capone Gangster Tour in Chicago

Private Al Capone Gangster Tour in Chicago

star-5
2
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
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Chicago Night Crimes Bus Tour

Chicago Night Crimes Bus Tour

star-4.5
47
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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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Chicago's Original Gangster and Prohibition Tour

Chicago's Original Gangster and Prohibition Tour

star-4
69
Book in advance to take this popular tour that details the mob history of Chicago during the Prohibition Era (1920s-1930s). Learn about the exploits of gangsters like Capone, Dillinger, Moran, and others as you travel by minibus to sites like the Biograph Theater, Holy Name Cathedral, and St. Valentine's Day Massacre. Your guide adopts gangster attire and characteristics that add dramatic flair to the historical commentary.
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  • 1 hour 45 minutes
From
$41.60
From
$41.60

Private Haunted History of Chicago Ghost Tour

Private Haunted History of Chicago Ghost Tour

Discover spooky stories in the Windy City on a private haunted history tour. Visit places with names such as the Murder Castle and Death Alley, and hear about Al Capone and the Old Congress Hotel. See all three locations on one tour that reveals fascinating details about historical events, and rumors of murder and mayhem in Chicago.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size
Taking safety measures

Chicago Haunted Halloween Segway Tour

Chicago Haunted Halloween Segway Tour

star-4.5
4
Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a Segway at night! Venture through the dark with your local guide, and see alleys, hotels and sites of some of the most gruesome disasters and murders in Chicago’s history. During your spooky adventure through the city, you’ll also see Chicago's famous landmarks lit up in glistening lights. Join in the Halloween fun all October long! Costumed guides and ghoulish tales--this haunting good-time is not to be missed!
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  • 2 hours
From
$75.58
From
$75.58

Original Chicago Haunting Ghost Bus Tour

Special Offer

Original Chicago Haunting Ghost Bus Tour

Our classic Chicago Hauntings Chicago Ghost tour is a 2.5 to 3-hour fully-narrated tour by coach bus, with numerous stops along the tour route at some of the most actively haunted sites in Chicago, including the site of the Eastland Disaster, where 844 souls perished on the Chicago River; Death Alley, where more than six hundred children and their chaperones lost their lives in the worst single building fire in American history; the site of the infamous St. Valentine’s Day Massacre in storied Lincoln Park, the original and the now abandoned City Cemetery, where an estimated 13,000 unmarked graves remain. Some of our most common stops include murder sites, disaster sites, cursed skyscrapers, gangland sites, Chicago’s most haunted house, and others. You are welcome to take photos at all of our stops — sometimes your camera may capture more than just spooky scenery.
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  • 2 hours 30 minutes to 3 hours
  • Taking safety measures
From
$39.20
$49.00
$9.80 savings
From
$39.20
$49.00
$9.80 savings
Taking safety measures

Pilsen Walking Tour of Local Publicly Displayed Art

Pilsen Walking Tour of Local Publicly Displayed Art

We find quality art from around the city by local artists that have significance towards local artists. Unique opportunity to appreciate homegrown art from local Chicagoans and to receive artistic inspiration.
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  • 1 to 2 hours
  • Free Cancellation
From
$15.00
From
$15.00

West Town Instagram Hot Spots Tour By Native 312

West Town Instagram Hot Spots Tour By Native 312

star-5
3
Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene.
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  • 1 hour 30 minutes to 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$25.00
From
$25.00
Taking safety measures

Wabash Arts Corridor Instagram Hot Spots Tour By Native 312

Wabash Arts Corridor Instagram Hot Spots Tour By Native 312

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene. Located in the heart of downtown Chicago, the Wabash Arts Corridor is the brainchild of Columbia College Chicago. The WAC is an urban outdoor exhibition featuring world class, large-scale works of public art. The heart of WAC is Wabash Avenue from Van Buren to Roosevelt and is framed to the east by Michigan Avenue and to the west by State Street. As an added bonus, this gallery is located amidst historical Chicago buildings with as story as colorful as the murals that don the exterior. Artists included in the tour: Collin van der Sluijs (Netherlands) Amuse 126 (Chicago) Justus Roe (Chicago) Renee Robbins (Chicago) Don’t Fret (Chicago) And many more!
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  • 1 hour 30 minutes to 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$25.00
Price varies by group size
From
$25.00
Price varies by group size
Taking safety measures

Pilsen Instagram Hot Spots Tour By Native 312

Pilsen Instagram Hot Spots Tour By Native 312

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What better way to explore a new neighborhood but with a local artist in tow to give expert commentary on the vibrant history and culture of the Chicago Art Scene. Pilsen owes its' name to the Czech population that emigrated here in the late 19th century, but is now home to one of Chicago's biggest Mexican populations and a hot bed for new & exciting art. The rich Mexican heritage can be seen throughout the neighborhood; everywhere from the Mexican Heritage Museum to the numerous murals found all throughout. Explore this neighborhood and it's rich culture new & historic with us.
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  • 1 hour 30 minutes to 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$25.00
From
$25.00
Taking safety measures

Logan Square Instagram Hot Spots Tour by Native 312

Logan Square Instagram Hot Spots Tour by Native 312

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our guide's extensive knowledge of Street Art and the local Chicago Art Scene. Murals by Artists on the Tour: JC Rivera Greetings From Tour Shawnimals Frank Quintero Sentrock And much more!
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  • 1 hour 30 minutes to 1 hour 50 minutes
  • Free Cancellation
  • Taking safety measures
From
$25.00
From
$25.00
Taking safety measures

Fright Hike: Chicago Halloween Bike Tour

Fright Hike: Chicago Halloween Bike Tour

star-5
2
Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.99
From
$49.99
Taking safety measures

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