Top Chicago Tours, Sightseeing & Cruises - page 4

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.

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.

Discover the dark side of the Windy City on this nighttime crime history bus tour of Chicago. Through your expert guide's rich storytelling, immerse yourself in tales of notorious mobsters like Al Capone, Frank Nitti, and Bugs Moran as you explore infamous crime scenes including the site of the St. Valentine’s Day Massacre.

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

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.

Do you have what it takes to solve puzzles, figure out clues, and flee your escape room—all in just 60 minutes? Find out when you book a Chicago escape room experience. Pick from five themed rooms: The California-themed Gold Rush; Special Ops: Mysterious Market, where you play secret agents; Prison Break, where you escape from a warden; the extraterrestrial-themed Mission: Mars; and the Heist, where you track down an art thief.

Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own with a private, self-guided app tour. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and more. With your GPS cuing your audio experience, this tour lets you go at your pace, style, and time, with lifetime access and no expiry.

Enjoy a fun and time-saving way to explore the best of Chicago on this small-group, guided Segway tour. Visit popular Grant Park and see Buckingham Fountain, plus optimal views of the Windy City skyline. Glide along the Lakefront Trail, taking in the Field Museum, Shedd Aquarium, Soldier Field, and beyond. Guided Segway training and helmets are included on this beginner-friendly outing.

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.

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk on this private, self-led smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid for an entire year. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

Hook up with a paranormal investigator to tour Chicago's Lincoln Park and look for paranormal activity. Stroll through the neighborhood and learn about the Great Fire of 1871, Suicide Bridge, the St. Valentine's Day Massacre, and visit Lincoln Park, and the old City Cemetery. You'll get the chance to try out some of the ghost-detecting equipment.

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

Chicago is renowned for its dynamic dining scene—and this private walking tour offers a personalized introduction to its must-eats. Pick a time that works best for you, and head to Gino’s East: one of the city’s classic deep-dish pizzerias. From there, set off on a tour of the Loop, where you’ll taste sweet and savory treats—and learn about the city’s architecture, history, and culture as you go.

Discover the creative side of Chicago beyond the city limits with this small-group tour of suburban hidden gems! Visit charming historic districts, offbeat local landmarks, striking public art, scenic waterfronts, and under-the-radar eateries as your expert guide shares insider stories you won’t find in guidebooks. With transport included and group size kept small, it’s a relaxed, camera-worthy way to explore unique neighborhoods, architectural treasures, and distinctive local culture. Ideal for repeat visitors, adventure seekers, or anyone curious to see more than the Magnificent Mile.

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

Discover Chicago architectural treasures—and immerse yourself in the Windy City's history—on this small-group walking tour. Your focus is the iconic stained glass pieces crafted and designed by the Tiffany Glass and Decorating Company. Following your guide from the Chicago Architecture Center, visit four late-19th-century landmarks that contain glass works by Louis Comfort Tiffany and his contemporaries. This in-depth, insider tour is a must-do for history and architecture fans.

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

Learn all about the history beyond one of Chicago’s best-known thoroughfares—and spot numerous architectural icons as you go—on this small-group walking tour of the Magnificent Mile. Meet your guide at the Chicago Architecture Center and set off to soak up the street’s ambiance, and discover highlights like the Wrigley Building, John Hancock Center, and more. Entry to the Chicago Architecture Center is also included, so you can extend the experience.

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

Chicago is world-renowned for its architecture—and this small-group walking tour offers the ideal introduction to its iconic buildings, its architectural eras, and the starchitects who have left their impression on the city. Meet your guide at the Chicago Architecture Center and set off on foot: you’ll discover highlights like the Wrigley Building and Marina City, will see works by Renzo Piano and Frank Gehry, and will learn all about Chicago history.

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.