Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, foll... More

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our loop around "Da Loop" we will peel back the layers of this Great Big ... More

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy st... More

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop.... More

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the ... More

Get a taste of Chicago on this small-group walking food tour and explore the specialties of River North neighborhood. Dive deeper into the culinary history of the place while trying out the best dishes to illustrate different cuis... More

Meet your tour guide at the beautiful Chagall Four Seasons mosaic as we begin our Creativity & Community neighborhood tour. After a short walk, we'll catch the Pink Line at the renovated Quincy L station (opened in 1897) and make ... More

Discover a new side of Chicago with Insta Walk! I offer stylish photos, cool angles, and creative ideas during our relaxed and friendly stroll. I'll use both iPhone and Polaroid cameras to capture your best shots. You'll get abou... More

Taste fresh baked goods, Chicago Deep Dish, 'snappy' Chicago Hot Dogs, and more as you unravel a mystery! The Chicago Murder Mystery Food Tour is an interactive and tasty experience that combines history, game-play, and a delici... More

The perfect tour for first timers to Chicago or those who want to explore Chicago's top attractions and highlights. Stroll through the beautiful streets of downtown Chicago and learn about the City’s rich history, colorful chara... More

Take a tour of Chicago Loop's Pedway system, a network of underground pedestrian tunnels. We'll also go above ground to view some special Chicago sights. Our tour begins in the lobby of the Swissotel with a brief overview of the ... More

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most prominent neighborhoods of the city and immerse yourself in its taste... More

Fell the tug of history and dive into the breathtaking events of the past. On this intriguing and unusual tour, you will explore another side of famous locations and get acquainted with haunted places filled with a spirit of gangs... More

Explore Chicago's rich history and vibrant culture on a walking tour starting at Millennium Park with the iconic Cloud Gate sculpture. Wander through lush gardens and public art, then delve into the Chicago Pedway's hidden gems. E... More

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognize... More

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 & Sou... More

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and more! Get... More

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 Nor... More

We start our tour at one of the most interesting buildings in the Loop — the Fine Arts Building.  Built in 1884 as a showroom and office complex, the building was converted later into its present-day use. Then we're off to the... More

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator. Like Ursula, all of our guides are all real ... More