Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour. After the World's Co...

View Art Deco masterpieces built in the heart of Chicago’s financial district during 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 and ...

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...

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and discover how they transformed Chicago into a center of skyscraper design and engineering...

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 unique tour will give you a complete overview of Chicago's architecture. While listening to the history of the city, you will see, in chronological order, some of its oldest buildings, as well as ultra-high towers of recent construction....

Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly...

The West Loop (or Restaurant Row) Donut Tour is a sister tour to our Original Downtown Tour. Geared towards those who want to see Chicago’s authentic foodie focused food scene, this is the tour for you! We’ll start on the west side of the loop an...

Chicago's Riverwalk is a bevy of impressive buildings, gardens, eateries, and beyond. Spend two hours wandering with an expert local at your side. Explore the art, architecture, and all the little hidden spaces with the absolute best experience in on...

Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the c...

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some...

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fas...

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Chicago and hear some of its most famous and creepy haunted stories. 21+ only. A costumed gu...

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people overlook on a daily ba...

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour was born. This tour...

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to understand how pizza evolve...

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. Along the way, we'll discuss some of the people, and people groups, that have helped to ...

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 twelve years later into its present-day use. We then venture a few blocks...

Get ready to experience beautiful and unique public art. Meet your guide in front of Chagall’s “Four Seasons” mosaic in the Loop. Next, we’ll board the Pink Line train at the historically-restored Quincy L Stop (1897) and make our way to Pils...

Chicago has it all – amazing architecture, great food, and iconic sights both old and new. This tour takes you to some of the city’s best spots alongside a local guide where you’ll get the inside scoop on what makes Chicago so special. Not only...