Skip to content

Explore Stunning Architecture Interiors

Rated 4.92 out of 5 from 631 reviews.Chicago, United States

Paused through August 27.

To protect the health of our community, Airbnb Experiences in many regions are paused due to COVID-19. Visit the Help Center for the latest updates before you book.

Experience hosted by Hillary

2 hours
Up to 10 people
Hosted in English

What you'll do

Explore world-famous Chicago architecture inside and out!

We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs!

Hillary's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
From $30
/ person
Sat, Aug 29
11:00 AM - 1:00 PM
Join 2 other guests
$30 per person
$30 per person
Sun, Aug 30
11:00 AM - 1:00 PM
$30 per person
$30 per person
Mon, Aug 31
11:00 AM - 1:00 PM
$30 per person
$30 per person

Meet your host, Hillary

Host on Airbnb since 2012
  • 631 Reviews
  • Identity verified
I am the owner & head tour guide at Chicago's #1-rated walking tour business on TripAdvisor, Inside Chicago Walking Tours. After several years in Chicago's river tour industry, I started my own walking tour business in 2014 in order to be able to show people the street-level and interior views of Chicago's world-famous architecture. Not only is my company ranked #1 tour out of more than 300 on TripAdvisor, it's also been featured in numerous online publications as a "best of Chicago" tour. I'm also responsible for creating the tours and training the guides who earned Chicago's architecture river tour a spot in the 25 BEST TOURS IN THE WORLD on TripAdvisor. My company’s tours are the opposite of the big-brand, scripted tours. We specialize in truly unique, personalized experiences of Chicago. Thank you for supporting small business!
I am the owner & head tour guide at Chicago's #1-rated walking tour business on TripAdvisor, Inside Chicago Walking Tours. After several years in Chicago's river tour industry, I started my own walking tour business in 2014 in order to be able to show people the street-level and interior views of Chicago's world-famous architecture. Not only is my company ranked #1 tour out of more than 300 on TripAdvisor, it's also been featured in numerous online publications as a "best of Chicago" tour. I'…
To protect your payment, never transfer money or communicate outside of the Airbnb website or app. Learn more

Where you'll be

We'll be staying in downtown Chicago ("the Loop") -- central to everything else you'd like to explore in the city before and after the tour -- and we will be covering a distance of 1.5 miles at a leisurely pace.

Rated 4.92 out of 5 from 631 reviews.

Patrick
March 2020
Hillary was great! We had a smaller tour so we were really able to have conversations about everything she was showing us. The architecture was just spectacular and there is no way my wife and I would have just stumbled upon the buildings and gone in for a look. It was great that she was able to give us history about what we were seeing and her own personal thoughts :) Highly recommend the tour!
Hillary was great! We had a smaller tour so we were really able to have conversations about everything she was showing us. The architecture was just spectacular and there is no way…
Joseph
March 2020
This is a really nice tour that stayed with us throughout the weekend, helping us to look a little differently at the city around us and appreciate it more fully. Adam was an outstanding host and guide, with great information and a dynamic approach to presentation.
This is a really nice tour that stayed with us throughout the weekend, helping us to look a little differently at the city around us and appreciate it more fully. Adam was an outs…
Greg
December 2019
RUN, don’t walk, to this tour! We’ve been on other walking tours but this one is a must-do if you are visiting Chicago. Hilary welcomes you and makes you feel like a friend. Her knowledge is stupendous! Again, make sure this tour is on your list of things to do in the Windy City!
RUN, don’t walk, to this tour! We’ve been on other walking tours but this one is a must-do if you are visiting Chicago. Hilary welcomes you and makes you feel like a friend. Her…
Jeffrey
December 2019
Hands down one of the best architectural walking tours in Chicago! Hillary made it fun, interesting and she is incredibly knowledgeable of the different periods of architecture. Most of all Hillary loves what she does and you can she it her passion. Thanks for a great tour J & G.
Hands down one of the best architectural walking tours in Chicago! Hillary made it fun, interesting and she is incredibly knowledgeable of the different periods of architecture. Mo…
Tiffany Anne
December 2019
Did the tour with Adam and I had an excellent experience. I would certainly recommend it to travellers looking to see beautiful architecture and design as well as learn about Chicago’s history and it’s notable residents and patrons. Adam was a highly engaging storyteller and guide: merci encore!
Did the tour with Adam and I had an excellent experience. I would certainly recommend it to travellers looking to see beautiful architecture and design as well as learn about Chica…
Rebekah
December 2019
See sights that the rest of the crowds are missing! This is the tour you didn't know you needed. Go inside buildings you'd never guess are publicly accessible and see interiors that will literally take your breathe away. Words don't do justice to the beauty of the interiors visited during this tour. I would recommend this tour to anyone over any other popular architecture tour. We had a Chicago resident in our group that was just as wowed as the tourists-a true testament to how unique and "off the beaten path" this tour is. If I ever visit Chicago again, this will be the first thing that I schedule to do again!
See sights that the rest of the crowds are missing! This is the tour you didn't know you needed. Go inside buildings you'd never guess are publicly accessible and see interiors tha…

Choose from available dates

6 available
1 / 2

Things to know

Cancellation policy

Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 10 guests of all ages can attend.

More tips

Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella.

What to bring

Camera

Umbrella (if needed)