Top Chicago Cultural Tours

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore the birthplace of the skyscraper, visit landmarks like the Chicago Theatre, the Pablo Picasso at the Daley Plaza, and Millennium Park, and see how the city rose from the Great Fire to define modern design. Led by a friendly local guide who’s passionate about Chicago’s history and architecture, this tour brings the skyline to life one building, story, and photo stop at a time. Whether you’re an architecture enthusiast, a first-time visitor, or a curious local, you’ll walk away seeing Chicago in a whole new way.

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.

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.

Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you through iconic landmarks, historic streets, and cultural sites, sharing authentic stories and insights along the way. Perfect for first-time visitors or those short on time, it’s a quick yet meaningful introduction to one of Chicago’s most vibrant neighborhoods. A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

Immerse yourself in Chicago’s rich and dynamic African American heritage during this half-day tour. Highlights include interior visit to an African American museum, a stop at the birthplace of gospel music in Bronzeville, and a look at the Obama home in Hyde Park and Jennifer Hudson's childhood home.

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable car ride for breathtaking views. Continue to Galena, a beautifully preserved historic town where 80% of the buildings are listed on the National Register of Historic Places. Here, you’ll visit the Ulysses S. Grant Home and take in the serene beauty of Grant Park. With a total travel distance of 325 km from Chicago, this tour offers the perfect blend of history, scenery, and relaxation before heading back to the city.

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.

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

Take a deep dive into Chicago's food scene on a small-group walking tour. Head for several of the city's most-notable eateries, including Billy Goat Tavern, known for its "cheezborger," Pizzeria Uno, birthplace of Chicago’s legendary deep-dish pies; and Al’s Beef, a favorite since 1938. Along the way, hear about the friendly rivalry with New York's pizza scene, Chicago's meatpacking roots, 1920s speakeasies, gangsters, and more.

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by experienced local guides, your tours dives deep into the neighborhood’s rich heritage, hidden landmarks, and cultural traditions. Unlike generic tours, we bring you behind the scenes with insider stories, community connections, and exclusive access to local favorites. Experience Chinatown through the eyes of those who know it best. A minimum of 2 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

Discover Chicago’s infamous gangster past on a private, fully personalized tour through the city’s historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events of the 1920s and 1930s. Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history. Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.

Discover Chicago's soaring ambition and neighborhood soul with your self-guided audio tour, allowing you to explore America's most architecturally significant city at your own pace. Begin at Millennium Park where Anish Kapoor's Cloud Gate reflects the skyline that pioneered skyscraper design and continues to push architectural boundaries today. Wander along the Chicago Riverwalk where boat tours explain how the city reversed the river's flow and rebuilt in steel and stone after the Great Fire of 1871. Marvel at the ICAs world-class collection. Explore the Magnificent Mile's shopping and historic Water Tower, then discover the vibrant neighborhoods where Polish, Mexican, and African American communities have shaped Chicago's culture. Experience the blues at clubs where Muddy Waters and Buddy Guy defined a genre, then savor deep-dish pizza in the taverns that perfected this Chicago original.

Skip the guesswork and discover the real haunts of Capone, Dillinger, and The Outfit on a walking tour that then also you shows how those same streets become movie stars. Walk the city 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.

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike. Explore Chicago’s iconic riverfront skyscrapers and historic bridges See legendary architecture including Willis Tower and Marina City Discover the heart of Chicago’s financial, civic, and architectural power Pass by Millennium Park and spend time at Cloud Gate (The Bean) Enjoy a panoramic Chicago skyline view, included for all guests

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

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.

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Queen’s Landing, where the city meets the lake, and the skyline stretches as far as you can see. You'll learn the history of the city, see the sites, learn about what you are seeing and be guided step by step by our walking tour app.

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.