Top Chicago Pop Culture

Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

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.

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Hook up with a paranormal investigator to tour Chicago's Lincoln Park and look for paranormal activity. Stroll through the neighborhood and learn about the Great Fire of 1871, Suicide Bridge, the St. Valentine's Day Massacre, and visit Lincoln Park, and the old City Cemetery. You'll get the chance to try out some of the ghost-detecting equipment.

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

Get an exclusive behind-the-scenes look at the hit TV show *Chicago P.D.* on this small-group tour of the set and beyond. Visit real filming locations including the Firehouse 51 exterior, Molly’s Bar, District 21 Station (UIC Police HQ), Millennium Park’s Bean, and the stunning Chicago Cultural Center and hear insider stories that you'd miss on your own.

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.

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

Calling all fans of the paranormal, this evening ghost bus tour of Chicago takes you into the city’s darkest recesses—and reveals a side of the city few others get to experience. Travel with ease between locations where hauntings are reported to have taken place and listen to chilling tales delivered by your guide. The City Cemetery, the site of the notorious St. Valentine’s Day massacre, and more are all included.

We are the original, top-rated Gangsters and Ghosts tour! As a private tour, hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your private 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 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.

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

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.

Get a closer look into how alcohol flowed through the streets of Chicago! From the “down and dirty” gangster hangouts, to the “jackets required” establishments for Chicago’s elite, learn what it took for all Chicagoans to get their booze!

Take a deep dive into the world of "Chicago Fire" and learn more about what it’s like behind the scenes of your favorite show on this private tour. Visit filming locations such as the exterior of Firehouse 51 and Molly's Bar, and popular tourist attractions, including the Bean at Millennium Park and the Chicago Cultural Center. Plus, enjoy handy hotel pickup if your accommodation is within five miles of downtown Chicago.

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On today’s Chicago Film and Television Tour, you'll explore the city through the lens of movie magic. Begin at one of Chicago’s most iconic theaters, seen in The Blues Brothers and Transformers. Stroll through downtown streets flanked by skyscrapers featured in the Joker’s money truck chase scene in The Dark Knight. At Union Station, relive the dramatic staircase sequence from The Untouchables, where Kevin Costner’s character battles criminals as a baby carriage tumbles down. Visit the University of Chicago, whose Gothic architecture and academic prestige have made it a popular filming location. Along the way, admire Chicago’s rare mechanical lift bridges and architectural wonders that make the city a perfect backdrop for filmmakers. In Chicago, every corner holds a scene, and every street tells a story—waiting for you to explore.

Bored of traditional walking tours? Try an experience that mixes sightseeing with an engaging game in this murder mystery tour through Chicago. Play as a detective and a suspect as you wander through various neighborhoods and see the city. Learn about the real legends and crimes of Chicago while you try to solve a murder.

Explore downtown Chicago through the lens of movies and TV on this walking tour that takes you to the filming locations for *Ferris Bueller’s Day Off*, *The Untouchables*, *The Dark Knight*, *The Bear*, *the Blues Brothers*, and more. Along the way, your local actor-guide shares behind-the-scenes stories, trivia, and fun facts you won’t get from walking the city on your own.

Explore Chicago’s vibrant street art and creative neighborhoods on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares insights into the city’s artistic communities, mural culture, and the stories behind each neighborhood. Begin in Pilsen Murals District, famous for colorful public artworks celebrating local heritage, then visit the National Museum of Mexican Art to see traditional and contemporary exhibits. Continue along 16th Street Murals Corridor, featuring large-scale murals reflecting social movements and cultural identity. Next, explore Fulton Market, a trendy district filled with galleries, restaurants, and creative spaces, and finish at Wabash Arts Corridor in downtown, where towering murals create a striking open-air gallery. This flexible, door-to-door private tour offers an immersive, relaxed way to experience Chicago’s dynamic art scene and creative spirit.

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.

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

Chicago's prettiest neighborhood hides some of its darkest history. This self-guided audio tour takes you through Lincoln Park on your own schedule, with narration on your phone at every stop. Start at the Red Lion Pub on North Lincoln Avenue, long rumored to be one of the most haunted bars in the city. Stand outside the Biograph Theater, where the FBI gunned down John Dillinger in 1934. Visit the North Clark Street site of the 1929 St. Valentine's Day Massacre. Walk into Lincoln Park, laid over what was once the city's cemetery, then finish on the Lake Michigan shore at North Avenue Beach. No group, no in-person guide, and no fixed start time. Go at your own pace, stop for a drink along the way, and replay any story you like. All you need is a phone and headphones.

Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.

Channel your inner detective on this immersive, self-guided scavenger hunt through Chicago’s Loop! Step back to 1923 as you gather clues, solve a murder mystery, and unlock secrets of Prohibition-era Chicago. Your group receives a mystery kit, then follows a story-driven trail at your own pace—no app required. Observe real landmarks and hidden clues as you work together, making this ideal for friends, families, and groups seeking a hands-on, flexible adventure. The perfect blend of history, teamwork, and local intrigue in the heart of Chicago.

Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, grab a drink and enjoy the history of the men, women and locations (famous and infamous) that helped shape Chicago as we know it today.