Best Chicago Walking Tours in 2025

Chicago , Illinois

From $ 35.00

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) and a city ready and willing to accept them. Find out what set these buildings apart from their predecessors and how they helped set the stage for the future. If you’re interested in iconic buildings, public art, urban planning or government this is your tour. Find out the stories behind inland steel, Marina city, the IBM building and other "Mad Men" worthy skyscrapers. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 35.00

Chicago is the birthplace of the skyscraper: imagine what incredible stories of engineering feats it has to tell! Join Inside Chicago Walking Tours on our newest route — it’s Chicago’s ONLY engineering-themed tour! You’ll cover more than 150 years of engineering evolution, learning from a real engineer who makes the information accessible and graspable without ever dumbing it down. We believe that everyone can understand and be fascinated by these concepts if taught in an engaging and fun way. You’ll see a building from the “father of the skyscraper,” who was actually an engineer and a classmate of Gustav Eiffel. You’ll learn how a “haunted” building gets its reputation simply by settling unevenly on its “floating” foundation. You’ll marvel at how Chicago’s buildings handle gravity and wind. And as on all of our tours, you’ll visit the interiors of a few buildings to truly get that sense that you’ve seen inside Chicago!

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 $ 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

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 $ 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

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 $ 29.00

The Windy City is known for its food, architecture, and haunting history! Walk with us as the sun sets through downtown Chicago, hearing some of the most gruesome and creepy Chicago stories. The first stop is the Congress Hotel, the most haunted hotel in Chicago. Walk along the streets that H. H. Holmes, Chicago's first serial killer, wandered as he stalked his prey, get a glimpse of Chicago’s sordid past through stories of the Everleigh Club and the 1900s Red Light district, and learn about downtown prison breaks.

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 $ 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 $ 29.00

Learn the history that makes the Chicago River and its recently updated Riverwalk historically unique.   Chicago is home to one of the world’s most recognizable and celebrated skylines and the Riverwalk’s intimate vantage provides an ideal perspective from which to learn and appreciate its incredible buildings.Discover Chicago's Rich History and Iconic Architecture Experience the vibrant tapestry of Chicago’s past and present with our Chicago Riverwalk Tour. Perfect for history buffs, architecture enthusiasts, and curious visitors, this 2-hour guided tour uncovers fascinating stories and architectural marvels that define the Windy City.

Chicago , Illinois

From $ 8.13

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 $ 29.00

Join us for an unforgettable 2-hour walking tour through the downtown Loop area and the iconic Millennium Park. This guided experience is perfect for visitors who want to uncover the vibrant history, breathtaking architecture, and artistic gems of Chicago. See the Chicago Theatre, where you'll marvel at its classic marquee and learn about its fascinating past as the "Wonder Theatre of the World." Stroll through the bustling streets of the Loop, exploring its architectural marvels and engaging in stories about the city’s dynamic history. We'll visit Millennium Park, a cultural and artistic centerpiece of Chicago. You'll have the chance to admire Cloud Gate—affectionately called "The Bean"—and take in its stunning reflection of the city skyline. Throughout the tour, your knowledgeable guide will provide engaging commentary, insider tips, and photo opportunities to ensure this is a Chicago experience you’ll never forget.

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.

Chicago , Illinois

From $ 14.99

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurants during the summer months, seating areas to relax, boat rentals, and theater-style seating for various performances. Other attractions along the Riverwalk include the Vietnam Veterans Memorial Plaza, and the McCormick Bridgehouse & Chicago River Museum and if you are lucky enough, see a bridge lift from inside the bridge house. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months. This isn't an entrance ticket. Check opening hours before your visit.