Explore Chicago by walking through the foundations of modern architecture itself, from the glory of the "Father of the Skyscraper" to Chicago's very own style.

If history were taught in the form of stories, it would never be forgotten.
— Rudyard Kipling

About This Tour Route...

Here, in the “City of the Big Shoulders,” America saw its first skyscraper, a daring, innovative, steel-framed “giant” of its time — though only 1/10 the height of the current tallest building in Chicago.  And though you can no longer see this revolutionary building, Inside Chicago Walking Tours specializes in getting you as close as possible to that moment in history:  not only will you see the exact spot where it once stood — something you’d likely see on other walking tours — but you’ll also see a comparable building designed by the same architect, at the same time, of the same height and same style — something you’d surely miss on other walking tours.  And it’s in this engaging, contextualized approach to teaching history that Inside Chicago Walking Tours sets itself apart, making Chicago’s architecture come alive for tourists and Chicagoans alike: we know how to set the right context for learning about the past through the lens of the present; we know how to make the stories behind the walls come alive. 

Inside Chicago Walking Tours takes you on a well-walked path of Chicago’s historical architecture, but in its unique, entertaining, and memorable way.  We promise you’ll be looking at architecture — and history — in a whole new light!

Chicago’s Loop, a lively mix of history, business, art, and culture, contains so much to experience, we had to separate it into three tour routes!  Come explore some of the most important historical architecture of downtown Chicago with Inside Chicago Walking Tours, and get to know this architecturally significant city from past to present. 

On this Brand New tour, you will:

  • 120-year-old walls that tell the fascinating story of modern architecture’s evolution;

  • Elevators so old, they still need to be operated by people inside them;

  • The only Frank Lloyd Wright space you'll find in downtown Chicago (believe it or not!);

  • Haunting, hidden faces that let an architect gaze at you from the past;

  • Amazing Tiffany stained glass mosaics, determinedly saved from destruction;

  • Much, much more!


  • Mondays at 2pm

  • Tours last 2 hours

  • Tours cover 1.5 miles on foot

  • Tour is led by Hillary.

  • Ticket prices:

    • $30 general admission (ages 11 and up)

    • $25 children (ages 6-10) and seniors (65+)

    • Free for kids under 6

  • Runs rain or shine, unless otherwise noted.

  • Tour starting point given upon ticket purchase. Check your ticket!