Best Chicago Walking Tours in 2026

Chicago , Illinois

From $ 35.00

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy bars, sites of real life mob shootouts, and haunted tragedies that shape the city's legacy. This walking tour blends ghost stories, true crime history, and architectural landmarks to reveal the beauty and horror from one of America's most famous time periods, right where it happened. You'll gain special access to architectural interiors tied to famous history, as you are led by a trained historian tour guide through these famous sites. Learn where Chicago's history still whispers after dark!

Chicago , Illinois

From $ 30.00

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theatre stage and discover the backstage artist signatures, including from legends like Frank Sinatra, Dean Martin, and Dolly Parton** Access to the grand lobby with its famous marquess, the auditorium with its classic atmospheric design, the iconic Chicago theatre stage and backstage areas including dressing rooms** Learn about the theatre’s unique architectural features, like a stunning French Baroque design, ornated plasterwork, and the gran chandelier along with its rich history and cultural significance* *Tour content is subject to change. There is no stage or dressing room access on concert days. Photo restrictions may apply.

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 $ 35.00

On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown. You’ll learn about the origins of some world-famous Christmas characters — some of them from Chicago, some not — as well as the history behind Christmas traditions practiced by people around the world.

Chicago , Illinois

From $ 34.99

Leave the little ones at home and step into the shadows for a spine-chilling evening designed exclusively for adults. Not all spirits in Chicago are content to rest in peace—and not all hauntings are friendly. On our Wind & Souls: Adults-Only Ghost Tour, we’ll peel back the veil of the city’s darker past to reveal the sinister specters that still lurk in its alleyways, abandoned buildings, and forgotten corners. These are the tormented souls of murderers, madmen, and those who met their end in the most tragic of ways. This tour isn’t for the faint of heart. You’ll hear about the cursed, the vengeful, and the downright malevolent spirits whose presence still chills the air and unsettles the soul. Wind & Souls is a mature, adults-only experience, featuring explicit historical details, strong language, and unsettling true stories pulled from the shadowy depths of Chicago’s haunted past.

Chicago , Illinois

From $ 35.00

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.

Chicago , Illinois

From $ 34.77

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain.   Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.

Chicago , Illinois

From $ 35.00

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 35.00

Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hear of hidden mob headquarters, psychopaths in plain sight, and disasters like the Iroquois Fire and Eastland Disaster. Join us in exploring historic interiors where gangsters once gathered and ghosts are said to linger. Along the way, explore the roots of ghost lore—are they real sightings or tricks of architecture? Decide for yourself if Chicago’s most haunted tales are fact or fiction. Perfect for fall nights and curious minds, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience.

Chicago , Illinois

From $ 15.00

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

Chicago , Illinois

From $ 30.00

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

Chicago , Illinois

From $ 29.99

Millennium Park is home to some of Chicago’s most cherished museums, sculpture, and greenery. It’s also the perfect place for an evening of ghost stories. Chicago has been burned down and rebuilt, and rebuilt all over again. Which makes these ghost stories the best way to see this city for what it truly is: a place haunted by itself and what it once was. Tales of massacres, disasters, demon children, and Dillinger await you.

Chicago , Illinois

From $ 6.97

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 $ 6.97

Get ready to explore Chicago Chinatown landmarks, hotspots, and popular restaurants all while playing the role of a brave Imperial Advisor to the Emperor of China. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. So, are you up for an exciting city game? Highlights include: • Explore Chinatown Square Plaza, Chinatown Mural, Chinatown Branch Chicago Public Library, and lesser-known places. • Enjoy a uniquely crafted story brought to you by our top-notch/gifted/talented writers. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt. After your booking, you will receive an email with instructions on how to download and play the game on your phone. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.

Chicago , Illinois

From $ 7.99

Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a delightful walk through time in this exclusive Chicago neighborhood. The starting point is the Chicago History Museum, located at 1601 N. Clark Street. The tour is ready whenever you are and the audio plays automatically at exactly the right time and place using your smartphone's GPS and the VoiceMap mobile app, which also works offline.