History isn’t just the big people, places, and events: it’s the little things — the unsung stories — that glue the pieces of the puzzle together.

What strange phenomena we find in a great city — all we need do is stroll about with our eyes open.
— Charles Baudelaire

About this tour route...

One of the benefits of researching and creating architecture walking tours is all of the fascinating discoveries one makes along the way – the hidden details and untold stories that add wonderful bits of color and texture to the overall narrative of a city.  Strolling around the streets of a major city like Chicago, as long as you have an engaging, knowledgeable guide who knows about the little things, your experience of the city will be so much richer than if you were simply shown the “big” things. The details people walk by every day will amaze you, and you’ll feel like you’ve truly seen a hidden side of Chicago by the end of your walking tour.

Inside Chicago Walking Tours knows the immense value of experiencing a city in this way, and has made an entire tour route from the “little things” – a truly unique collection of stories and details that will delight even the most Chicago-savvy tour participants.

The Loop is full of well-known architectural masterpieces, and is of course packed with history.  But history isn’t just the big people, places, and events: it’s the little things – the unsung stories – that glue the big pieces of the puzzle together, and that make Chicago the fascinating town it is today.  Let Inside Chicago Walking Tours take you on a tour through history via the small details – and get the “inside scoop” about the Second City.

On this Classic tour, you will See:

  • A peaceful sunken garden oasis in the heart of the city;

  • A gleaming classical interior with soaring glass ceiling;

  • The Harry Potter-esque "oldest" building in the Loop;

  • An artistic warning to over-ambitious politicians;

  • Much, much more!


  • Thursdays and Fridays at 10am (see Tour Calendar for extra days/dates)

  • Tours last 2 hours

  • Tours cover 1.5 miles on foot

  • Tour is led by Adam.

  • 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.