There’s something absolutely magical about the 1920s. The progressive spirit, the fashions, the architecture… yet something sinister lurks as well…

Architecture should speak of its time and place, but yearn for timelessness.
— Frank Gehry

About This Tour Route...

This BRAND NEW tour is the answer to many requests for an Art-Deco-specific tour because — let's face it — we all LOVE the elegance, glam, and glitz of the 1920s and 1930s. This 2-hour walking tour explores the interiors and exteriors of gorgeous buildings from these decades, with some interesting details and stories about life in that era. Flappers, gangsters, jazz, speakeasies — we'll pepper those throughout our larger exploration of Chicago's magnificent Art Deco buildings in order to truly set the context for you!

Inside Chicago Walking Tours brings you back in time on this much-anticipated tour.  You’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. You’ll understand why the Art Deco style is so timeless — why even for us, it has a stunning beauty that inspires us to this day. You’ll learn to look at this architectural style especially as a form of “marketing” for the ambitious people inside; you’ll learn to put yourselves in the shoes of people whose focus was on the future, and whose architectural context showed it.

Let Inside Chicago Walking Tours take you back in time, and enjoy these interior spaces that evoke thoughts of Metropolis, The Great Gatsby, and even Gotham City (we’ll explain that one…). Without ever having to leave Chicago’s central Loop neighborhood, we’ll explore the elegance of the “Roaring ‘20s” behind doors that people walk by every day. Come join us on our newest tour!

On this Timeless tour, you CAN SEE:

  • Vertically soaring spaces that purposely draw your eyes upward;

  • Gleaming materials all around — polished marble, brushed metal;

  • Symbolism carefully chosen by architects to celebrate buildings’ functions & stories;

  • A rarely seen old vault with a gorgeous 54,000-pound door;

  • Much, much more!


  • Schedule coming soon!

  • 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!