THE TOP 20 Chicago Pop Culture (UPDATED 2026)

Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

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Chicago Gangsters and Ghosts Walking Tour

2 hoursFree Cancellation

Price varies by group size

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Explore Chicago's legendary architecture and history.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

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Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

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Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

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Chicago Architecture and True Crime: Halloween Edition

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

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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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Chicago's Original Gangster Tour by Bus

1 hour 45 minutesFree Cancellation

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See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

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Chicago River Ghost & Dark History Night Cruise

1 hour 30 minutesFree Cancellation

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Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

1 hour 30 minutesFree Cancellation

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Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally led Pilsen walking tour offers an authentic, insider experience beyond typical Chicago sightseeing. - Pilsen-based experts with 40+ years of combined experience - Explore iconic sites like 16th Street murals, Thalia Hall, and local cultural landmarks - Official Pilsen tour partner of the Chicago History Museum - Bilingual tours available in English and Spanish - Multiple routes and flexible options, including walking, running, or biking tours -BOOKING: Please note the tour guide will contact you to schedule an exact time for your tour after you have completed the booking. There is no option to pick a start time.

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Pilsen Chicago Walking Tour: Street Art & Mexican History

1 hour 15 minutesFree Cancellation

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Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

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More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate. On this tour, you’ll hear how the culture in turn-of-the-century Chicago helped bring about the 18th Amendment through stories of notorious vice districts along the Chicago River and the South Loop. We'll talk about the rise of Al Capone during the infamous “Beer Wars,” culminating in the St. Valentine’s Day Massacre. Along the way, we’ll talk about how the city played a role in the popular and artistic growth of jazz, and how Chicago during the Roaring Twenties has been depicted on screen, in blockbusters such as "The Untouchables" and "Chicago." Please be advised that this tour contains stories of murder and sex work. Although children are welcome on this tour, parents should use their discretion in determining whether it is suitable for those under 15.

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Prohibition Chicago: Myth vs. Reality Walking Tour

2 hoursFree Cancellation

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Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

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Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer House, where Al Capone once mingled, and pass the Congress Hotel, rumored to be haunted by ghostly figures. Drive through Grant Park to learn about H.H. Holmes and the chilling Iroquois Theatre Fire. At each stop, delve into gripping tales of rivalries, secret doors, and tragic events that shaped Chicago's past. This tour is perfect for history buffs and those intrigued by the darker side of the city. - Explore key sites linked to Al Capone and Chicago's gangland history - Discover chilling tales of hauntings, Death Alley, and the tragic Iroquois Theatre Fire - Enjoy stops at iconic locations like the Holy Name Cathedral and Grant Park - Engage in a unique paranormal photo opportunity by the Chicago River

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Chicago Gangsters and Ghosts Minibus Tour

2 hoursFree Cancellation

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See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

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Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

2 hoursFree Cancellation

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Chicago Crime, Mobsters & Ghosts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.

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Burning Spirits Haunted Pub Crawl

2 hoursFree Cancellation

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Original Chicago Prohibition Bus Tour

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Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

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Chicago Haunted Interior Architecture Ghost Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

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Wind and Souls an Adults Only Ghost Tour in Chicago

1 hour 30 minutesFree Cancellation

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Learn about the history and legends surrounding the 1893 Chicago World's Fair and notorious criminal H.H.Holmes on a half-day tour inspired by the popular book ‘The Devil in the White City.’ Explore important locations such as the Prairie Avenue Historic District, Jackson Park, Midway Plaisance Park, and the ‘Murder Castle’ of H.H. Holmes as you learn more about the World's Columbian Exposition and Victorian Chicago.

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The Devil in the White City: A Haunting History Tour

3 hoursFree Cancellation

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For sightseers looking to put a spooky spin on their night and avoid the overpacked city tours that tell history most of us already know, this Chicago Family-Friendly Ghost Tour is just the thing. Stop at popular Chicago attractions, including the Flying Dragon sculpture, the Chicago Stock Exchange Arch, the Abraham Lincoln statue, and Buckingham Fountain, while a guide tells you ghost stories along the way.

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Haunted Chicago: Lincoln Park Ghost & History Walking Tour

1 hour 30 minutesFree Cancellation

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Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and the Eastland Disaster. You are welcome to bring your own beverages and food/snacks to fully enjoy your time on the water. Departing from the Chicago Riverwalk, this is a fun and engaging way to experience the spooky side of the city. This tour is typically smaller allowing for you to interact with the tour guide! Ask all the questions, we are ready! - 120-minute ghost tour on the Chicago River for up to 18 passengers - Fun bring-your-own beverage/snacks experience with a u-shaped bar and coolers - Learn about Chicago's haunted history and significant events - Departures from the Chicago Riverwalk—15-minute early arrival required to allow time for check in and depart on time.

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Chicago River Guided Ghost Tour

2 hoursFree Cancellation

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Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

Top Chicago Pop Culture in 2026

57 results

Must-Dos in Chicago

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River

Chicago Riverwalk

The Magnificent Mile

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago Theatre

Art Institute of Chicago

Chicago River