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

About This Tour Route...

Are you the adventurous type? 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 a top spot out of nearly 300 tours 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.

On this Always-Unique tour, you will:

  • See stunning architecture, inside and out;

  • Have the chance to experience the world-famous Chicago “L” train — or even take a water taxi if season availability allows;

  • Have the opportunity to make requests to tailor the experience to your own tastes and interests;

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

  • MUCH, much more!


  • Please refer to Tour Schedule for availability & booking.

  • Tours last 2 to 2.5 hours

  • Tours cover ~1.5 miles on foot

  • Tour is led by Hillary.

  • Ticket prices:

    • $40 general admission (ages 11 and up)

    • $35 children (ages 5-10) and seniors (65+)

    • Free for kids under 5

  • Runs rain or shine, unless otherwise noted.

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

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