Best Chicago Cultural Tours in 2025

Chicago , Illinois

From $ 35.00

The Chicago Murder Mystery Tour is an interactive history tour and game! 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

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and discover how they transformed Chicago into a center of skyscraper design and engineering. Highlights on this walking tour include Burnham and Root’s Rookery (1888), a transitional building with a Moorish and Romanesque exterior and a stunning interior atrium re-designed by Frank Lloyd Wright; Adler and Sullivan’s Auditorium Building (1889), a masterpiece of acoustical and structural engineering; and Holabird and Roche’s Marquette Building (1895), an outstanding example of the metal frame expression with traditional details and decorations. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

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 $ 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 $ 29.00

Learn the history that makes the Chicago River and its recently updated Riverwalk historically unique.   Chicago is home to one of the world’s most recognizable and celebrated skylines and the Riverwalk’s intimate vantage provides an ideal perspective from which to learn and appreciate its incredible buildings.Discover Chicago's Rich History and Iconic Architecture Experience the vibrant tapestry of Chicago’s past and present with our Chicago Riverwalk Tour. Perfect for history buffs, architecture enthusiasts, and curious visitors, this 2-hour guided tour uncovers fascinating stories and architectural marvels that define the Windy City.

Chicago , Illinois

From $ 8.13

The city sparkles with steel, glass and stolen art. You’ve just pulled off the heist of a lifetime, walking the streets of Chicago with Edward Hopper’s Nighthawks tucked in your bag. Now all you need is to disappear into the crowds, blend in as a tourist, and complete the handoff before anyone notices. No pressure. This thrilling self-guided quest takes you on a high-stakes escape through the iconic Eastside, from the legendary Millennium Park to striking sculptures, quiet plazas, and hidden corners. Your phone will guide you with precise directions as you solve clues, learn fascinating stories, and admire architectural marvels, all while staying one step ahead of the law. What makes this tour unique? It's an interactive thriller that turns Chicago’s art and architecture into the backdrop of your great escape combining culture, adventure, and a touch of mischief. Play solo or with friends. Walk, think, laugh, and see the city in a whole new way.

Chicago , Illinois

From $ 29.00

Join us for an unforgettable 2-hour walking tour through the downtown Loop area and the iconic Millennium Park. This guided experience is perfect for visitors who want to uncover the vibrant history, breathtaking architecture, and artistic gems of Chicago. See the Chicago Theatre, where you'll marvel at its classic marquee and learn about its fascinating past as the "Wonder Theatre of the World." Stroll through the bustling streets of the Loop, exploring its architectural marvels and engaging in stories about the city’s dynamic history. We'll visit Millennium Park, a cultural and artistic centerpiece of Chicago. You'll have the chance to admire Cloud Gate—affectionately called "The Bean"—and take in its stunning reflection of the city skyline. Throughout the tour, your knowledgeable guide will provide engaging commentary, insider tips, and photo opportunities to ensure this is a Chicago experience you’ll never forget.

Chicago , Illinois

From $ 35.00

Because we don't just show you the city... we tell you, and we make you live it! At ChicaGo Turismo you will discover the true essence of Chicago: its vibrant history, imposing architecture and hidden corners that few know. Our guides are passionate and certified experts, with charisma, solid knowledge and an authentic connection to the city. We offer 100% Spanish tours, designed especially for Spanish speakers who want to know Chicago thoroughly, with cultural context, fascinating stories and a touch of humor and excitement. We walk, explore, observe and feel each space with curiosity and respect, so that you live an unforgettable, close and authentic experience.

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 $ 22.68

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.