An "old vs. new" adventure for history buffs!  Explore the streets and buildings of downtown Chicago as they looked in the past...

Scars have the strange power to remind us that our past is real.
— Cormac McCarthy

About This Tour Route...

This brand-new tour route for 2018 was inspired by books like Lost Chicago and Chicago Then & Now.  Hillary, the owner of Inside Chicago Walking Tours and creator of all tour routes offered by her tiny company, found herself totally "geeking out" about old photos of Chicago, and enjoyed the challenge of figuring out the exact spots and angles from which the photos were taken.  In her research, she has uncovered such a wide and fascinating variety of Chicago "scenes" — some photographed, some hand-drawn before cameras were even around!  And what you'll see is only the tip of the iceberg!

With your lively and engaging guide, Adam, you'll "time travel" through nearly 200 years of Chicago street scenes, walking in the footsteps of countless people before you — workers, politicians, immigrants, activists — and seeing what they would have seen.  On this unique historical tour, you'll learn about such fascinating moments in Chicago's history like the building of the "L," the debut of the Art Institute, and the absolute chaos of the old riverside markets.  You'll be thrilled with the "then-and-now" approach to this tour, allowing you to time travel while taking a leisurely walk around downtown!

Come with Inside Chicago Walking Tours on this one-of-a-kind tour that will help you appreciate what Chicago is through what it was.  We'll take a nostalgic look back at the past of this great American city: as with all of our top-ranked tours, we can't wait to show you the "second side of the Second City."

On this Brand New tour, you will:

  • See scenes of desolation from after the Great Fire;

  • Picture the hustle and bustle of the city's old market;

  • Mourn the loss of some beautiful buildings from master architects — and learn where you can see surviving pieces;

  • Stand at the exact spot where Lincoln's body was laid out in state during his 3-week "funeral train" journey back home;

  • Visit what are officially the oldest buildings in downtown Chicago (hint: it doesn't include the Water Tower...);

  • Much, much more!


  • Coming soon! Stay tuned!

  • Tours last 2 hours

  • Tours cover ~1.5 miles on foot

  • 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.

  • Exact tour starting point given upon ticket purchase. Check your ticket!