An always unique, customized tour for those who want to get the most out of their time in Chicago!


About This Tour Route...

Hillary, founder of Inside Chicago Walking Tours and your personal tour guide on this route, created this tour option out of 1) her years of improv comedy experience and her love of challenging herself to cater to her audience’s interests on the spot, and 2) the absolute joy she feels giving private tours where she is allowed to make up the route as she goes along.  It's basically a private tour for a public tour price, as no two routes will be alike!  If you don't like the typical, big-company scripted tours, then this tour is for you — it is the antithesis of boring, scripted tours offered by most companies in Chicago.  No two tours will ever be the same, and you never know what you're going to end up seeing — but we guarantee you'll absolutely love the experience.  And come on, Hillary must be good at what she does to have earned her spot as #1 out of 220 Tours in Chicago on TripAdvisor!  (Want to see for yourself?  Click here!)

How does this tour work, you ask? Well, have you ever read one of those old “Choose Your Own Adventure” books? It’s sort of like an architecture walking tour version of that. We’ll begin our tour with a quick poll of the group for any “must-see” items and requests, and then — as long as it can be fit within 2 hours’ walk of our starting point — we’ll go do it! Perhaps you want to see more historical buildings, or perhaps you want to know about Chicago’s Pedway system, or perhaps you simply want to see some great views. It’s all possible on this always-improvised tour with your own personal expert guide at your disposal! Not sure what you want to see? No problem at all! Hillary will easily and gladly fill 2 hours with amazing content that she will personally curate for you on the spot.

So let's go on an adventure together!  Come with award-winning tour guide Hillary on this fresh and innovative interactive tour.  Who knows?  You might see early skyscrapers, or hidden secrets, or stunning gardens, or underground chapels... the sky's the limit!  Feeling adventurous?  Click below to reserve your spot today!

On this Brand New tour, you will:

  • See stunning architecture, inside and out;

  • Get personalized recommendations for experiencing the "best of" one of the most famous cities in the world;

  • Enjoy unique, personalized commentary and guiding from your highly knowledgeable and engaging guide — who is also the company owner;

  • 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.

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