Top 10 Cultural Tours in Chicago

Destination: Chicago.
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.
Known For: Chicago Historical Tours, Chicago Cultural Tours, Chicago Excellent Quality, Chicago Walking Tours, Chicago Crime Tours, Chicago New Product.
Duration: Around 1 hour and a half.

Destination: Chicago.
Take a tour of Chicago's Pedway system (a network of underground tunnels that allows pedestrians to pass from one end of the Loop to the other) and enjoy seasonal holiday decorations and sights along the way. Our tour begins in the lobby of the Swissotel where we descend into the Pedway. After a tour of the Chicago Cultural Center and its famous Tiffany Dome, we return to the Pedway for a short walk to Macy's department store. There, we'll view the famous Tiffany ceiling, the "Great Tree" in the Walnut Room and the store’s decorated holiday windows. We return to the Pedway and follow it to Civic Center Plaza for a visit to the Christkindlmarket, an authentic European holiday market. We return to the Pedway for a visit to City Hall followed by a short walk to a nearby L station. A quick train ride takes us to the origin/terminus of Route 66, the Art Institute’s lion statues, and Millennium Park to view the famous Cloud Gate sculpture, aka, The Bean and the city's holiday tree .
Known For: Chicago Historical Tours, Chicago Small Group, Chicago Likely To Sell Out, Chicago Walking Tours, Chicago Likely to Sell Out, Chicago Cultural Tours, Chicago Christmas, Chicago Private and Luxury, Chicago Half-day Tours.
Duration: Around 3 hours.

Destination: Chicago.
This is the only tour in Chicago that explores the movie "Ferris Bueller's Day Off" from the perspective of art. It's also the only walking tour that immerses you in the actual artwork featured in the 1986 American teen film. Over the course of the tour, you'll visit 3 floors of the museum, see 16 pieces of art, and leave with an appreciation of the works, their relationship to characters, and their placement in the camera's frame. ⚠️ NOTE: Admission to the Art Institute of Chicago is NOT included in the public walking tour. The tour starts under the stairs in the *Modern Wing* of the Art Institute, Griffin Court. Guests must digitally sign a general waiver of liability. Guardians must sign waivers for children under the age of 18.
Known For: Chicago Walking Tours, Chicago Likely To Sell Out, Chicago Cultural Tours, Chicago Movie Tours, Chicago Art Tours, Chicago Small Group, Chicago Likely to Sell Out.
Duration: Around 1 hour and a half.

Destination: Chicago.
Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.
Known For: Chicago Historical Tours, Chicago Walking Tours, Chicago Cultural Tours, Chicago Private Sightseeing Tours, Chicago New Product.
Duration: Around 2 hours.

Destination: Chicago.
One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most important sites and locations of Chicago. Being a private tour, stop whenver you want to take pictures and also explore by foot specific locations. Pick up is included from your hotel or place of choice inside the city and downtown Chicago. Please include this information as well as a contact number when booking. This private tour will give you a great experience to get to know Chicago. This is a 4 hour private tour with driver and separate tour guide. During this tour, you will explore great locations in Chicago like the Richard J. Daley Center. There will also be a photo stop at the Lakefront Trail and South Michigan Avenue. Don't miss the Grant Park, Cloud Gate and of course the Downtown / The Loop. This private tour will finish off at your hotel in Chicago.
Known For: Chicago Private Sightseeing Tours, Chicago Car Tours, Chicago Cultural Tours, Chicago Bus Tours, Chicago City Tours, Chicago Half-day Tours.
Duration: Around 4 hours.

Destination: Chicago.
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.
Known For: Chicago Cultural Tours, Chicago New Product, Chicago Crime Tours, Chicago Walking Tours, Chicago Historical Tours.
Duration: Around 3 hours.

Destination: Chicago.
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
Known For: Chicago Cultural Tours, Chicago New Product, Chicago Audio Guides, Chicago Private Sightseeing Tours, Chicago Architecture Tours, Chicago Walking Tours, Chicago Historical Tours.

Destination: Chicago.
Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to highlight the unique tastes, rich history, and vibrant culture of Chicago’s Chinatown. This comprehensive tour combines a curated food-tasting journey with an exploration of iconic landmarks, making it the most enriching and flavorful Chinatown experience available in such a short duration. All of the restaurants and shops we pick for you are our member businesses of Chicago Chinatown Chamber of Commerce with guaranteed food quality and hospitality! You get the most of your money and time! A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.
Known For: Chicago Food & Drink, Chicago Historical Tours, Chicago Best Conversion, Chicago Walking Tours, Chicago Cultural Tours, Chicago New Product, Chicago Half-day Tours.
Duration: Around 3 hours.

Destination: Chicago.
This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a whole different side of the city. The tour has 2 options: Wicker Park and Bucktown - faster pace, 2.5 miles of walking. Wicker Park only - slower pace, 1.5 miles of walking
Known For: Chicago Historical Tours, Chicago Private Sightseeing Tours, Chicago Cultural Tours, Chicago Walking Tours, Chicago City Tours, Chicago New Product.
Duration: Around 2 hours and a half.

Destination: Chicago.
Skip the crowds—this is a private tour for your group only! “Chicago’s Festive Lights: A Magical Christmas Journey” takes you through the heart of the Windy City during the most wonderful time of the year. Begin your tour at 875 North Michigan Avenue (formerly the John Hancock Center), adorned with holiday decorations and offering spectacular views of the city’s festive lights. Stroll down N State St, a vibrant street bustling with holiday shoppers and seasonal displays. Conclude your tour at Christkindlmarket Chicago, a traditional German holiday market filled with crafts, food, and the spirit of Christmas—an authentic and memorable way to experience the joy of a Chicago Christmas. Itineraries are subject to change based on availability.
Known For: Chicago Seasonal, Chicago Christmas, Chicago Walking Tours, Chicago Likely to Sell Out, Chicago Likely To Sell Out, Chicago Private Sightseeing Tours, Chicago Cultural Tours.
Duration: Around 2 hours.