Top Chicago Tours by Duration

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 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

Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the first Europeans to come through here, the Great Chicago Fire, the origin of the skyscraper, the 1893 World’s Fair, Prohibition and the creation of Millennium Park. Along the way, you’ll discover some of the Loop’s most beautiful interiors, found in buildings that thousands of people walk past every day, completely unaware of what’s inside…And how things created inside those buildings shaped our current world for the better. You’ll hear the stories of the men and women--including Jean Baptiste Point du Sable, Daniel Burnham, Potter and Bertha Palmer, and Muddy Waters--who made Chicago what it is today, and those, like Jeanne Gang, who are defining Chicago’s architectural future.

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.

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore the neighborhood with a local guide, you'll sample regional Chinese specialties, discover the stories behind each dish, and gain a deeper understanding of Chinatown's rich culture and history. Tea and ice water are included throughout the tour. - Sample authentic regional Chinese dishes at local favorite eateries. - Explore Chinatown with knowledgeable guides connected to the community. - Learn the cultural traditions and stories behind every tasting. - Enjoy an award-winning culinary experience curated by Z.J. Tong.

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.

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture. Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design. Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior (Ferris Bueller's Day Off), the Chicago Board of Trade exterior (The Dark Knight), Union Station's staircase (The Untouchables), and Millennium Park's Cloud Gate (Source Code). Enjoy a seamless and comfortable experience exploring these famous sites.

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

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.

Whether you’re a first-time visitor or are just looking for a stress-free way to sightsee, this private, full-day driving tour makes discovering Chicago’s top sights simple. Meet your guide in the morning at your hotel, and set off: see landmarks like Wrigley Field, Grant Park, Millennium Park (and “the Bean”) all in one day. Don’t forget to bring your phone or camera to capture memorable snaps en route.

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.

Experience Chicago like never before—and see more of the sights in less time—on this immersive bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the one-of-a-kind Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory, and much more. The use of a bike and helmet is included.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

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.