Chicago, Illinois Tours & Activities in 2026

Chicago , Illinois

From $ 35.00

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 35.00

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment. What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 15.00

The Chicago Architecture Center (CAC) was founded in 1966 as the Chicago Architecture Foundation to save the historic Glessner House. Since then, the CAC has grown to become one of the largest cultural organizations in Chicago. Visit the CAC to view our 4,250-building scale model of Chicago, shop in our award-winning store or participate in a fun family event in our ArcelorMittal Design Studio. On the Chicago Model, view more than 4,200 buildings in one spectacular room at the cinematic and interactive Chicago City Model Experience. At the Chicago Gallery learn how Chicago became the "city of architecture," with a look at its fascinating neighborhoods, housing styles and famous architects. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago , Illinois

From $ 16.00

In the heart of downtown Chicago, the American Writers Museum celebrates all genres of writing through interactive exhibits and programming. From Twain to Tupac, there's a story here for everyone. Discover for yourself and visit today! Named Illinois' Best Attraction by USA Today and One of the 10 Best New Museums in the World by Fodor's. Flexible Date Entry

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

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 $ 29.99

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

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 $ 34.00

Voted the #1 Immersive Art Experience in America by USA Today readers in 2024, Color Factory Chicago celebrates the joy of color. Guests embark on a bright and colorful journey through 14+ immersive installations that inspire joy and human connection, expand boundaries of perception, encourage play, and engage the senses in unexpected ways. Fun for all ages, each visit includes surprise giveaways, sweet treats, and complimentary digital photos. From the lobby to the gift shop and every colorful moment in between, our spaces are as inclusive as they are dynamic and celebratory. Each room is designed in partnership with an exceptional roster of local and international artists and collaborators. Jump into color with us! Please note: At least ONE person's ID must match the name on ONE ticket. If no one in your party has an ID matching the name on one ticket, you will not be allowed entry. Minors under the age of 18 will not be allowed inside without a parent or guardian.