Best Chicago Cultural Tours in 2026

Chicago , Illinois

From $ 35.00

You will solve a murder as you learn real Chicago history! Play detective as you unravel a murder mystery, and learn about Chicago's true crime legends and Prohibition secrets. This two-in-one experience combines a rich historical walking tour with an exciting award-winning murder mystery game. Perfect for people looking for a history tour of Chicago, and also for people looking for a chance to play and have fun. Explore a City, Solve a Murder! Only on the Chicago Murder Mystery Tour.

Chicago , Illinois

From $ 35.00

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. After the World's Columbian Exposition of 1893, Chicago was determined to become a great cultural and commercial metropolis. This tour is a testament to that era's ambitions. See buildings by Daniel Burnham, Louis Sullivan, Holabird and Roche and other noted architects and hear the stories behind the city's architectural gems. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 34.00

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago's darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.

Chicago , Illinois

From $ 35.00

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 30.00

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theatre stage and discover the backstage artist signatures, including from legends like Frank Sinatra, Dean Martin, and Dolly Parton** Access to the grand lobby with its famous marquess, the auditorium with its classic atmospheric design, the iconic Chicago theatre stage and backstage areas including dressing rooms** Learn about the theatre’s unique architectural features, like a stunning French Baroque design, ornated plasterwork, and the gran chandelier along with its rich history and cultural significance* *Tour content is subject to change. There is no stage or dressing room access on concert days. Photo restrictions may apply.

Chicago , Illinois

From $ 35.00

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons. Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 35.00

Mobsters and Movies takes you through the real haunts of Capone, Dillinger, and The Outfit—then shows you how the very same streets turned into movie magic. Walk the same corners seen in 'The Untouchables' and 'Public Enemies,' and hear how Chicago wrote the script for American gangster history. This isn’t just another sightseeing tour—it’s a front-row seat to crime, cinema, and the city that made them both. Your guides aren’t just storytellers—they’re trained true crime historians, film buffs, and Chicago insiders who bring every scene to life. Step inside exclusive interiors where real mobsters plotted and Hollywood crews once brought the Windy City to the Silver Screen. We take you deeper into the story than any other tour can. Expect vivid tales, insider trivia, and behind-the-scenes stories that make Chicago’s gangster past feel as real as the movies it inspired.

Chicago , Illinois

From $ 30.00

Discover the rich history and culture of downtown Chicago on this guided walking tour with local expert Dave Lineal. Stroll the city's streets and enter historic buildings while gaining insight with fascinating stories. This immersive experience is perfect for those looking to deepen their understanding of Chicago's unique heritage. - Guided walking tour led by local expert Dave Lineal - Explore downtown Chicago's streets and historic interiors - Learn about the city's history, economics, and culture - Ideal for history buffs and culture enthusiasts alike

Chicago , Illinois

From $ 9.99

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

Chicago , Illinois

From $ 9.75

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.

Chicago , Illinois

From $ 22.71

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the year 1923. You are a detective in Chicago and a woman has been found murdered. It’s now up to you to to solve the crime and finde the culprit. After your purchase, you go to the designated pickup point and collect the mystery package containing everything you will need to solve this mystery. When you have collected it, you are free to begin whenever you want. Enjoy the flexibility of starting and stopping as you please. Solving this murder mystery is an exciting and challenging activity that you can try together with your family, friends, or colleagues. You must be a minimum of 2 people to buy this. A good tip! We recommend 2-4 in a group. Note that this is only Available in english.