Top Illinois Pop Culture

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.

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.

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.

Swap the standard Chicago itinerary for the chance to experience a whole different side to the city. Walk in the footsteps of Al Capone and John Dillinger while hearing tales of Chicago's haunted past. This walking tour takes you to prohibition-era speakeasies, sites of real life mob shootouts, and provides special access to places tied to historical events that have shaped Chicago.

Explore a new side of Chicago and the city'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, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

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!

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

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.

Our goal is to disturb and unsettle you of whatever assumptions you may have about Chicago. We do so with our entertaining and brilliantly researched experiences, that highlight the historic gangster past of Chicago, and also shares the hidden beauty, natural wonders, and cultural highlights of America's third-biggest city. Guests walk away more historically oriented travelers, with a reason to visit Chicago again.

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.

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.

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.

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

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.

See a new side of the Windy City—and admire Chicago's dazzling skyscrapers and landmarks, all lit up after dark—on this sunset tour by open-top bus. While your on-board guide provides insights, check off the city's best-known attractions in just one tour, from Navy Pier and the Magnificent Mile to the Museum Campus, and the Loop's skyline.

Lots of tours help you explore Chicago’s historic streets, but most avoid the grittier details that have helped shape the city over the decades. But this small-group walking tour doesn’t shy away from the gruesome details. Listen to tales of gangsters, restless spirits, and local disasters as you navigate some of Chicago’s most popular landmarks.

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.

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.

Lovers of history, true crime, and haunted mysteries rejoice—skip the generic sightseeing tours and learn about Chicago’s dark underbelly with this mob history tour. Follow your guide through historic streets and alleys from Grant Park to the “Alley of Death”—also known as West Couch Place—as you learn about the city’s gritty mobsters, doomed ghosts, crime, and vice.

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.

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.

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

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.