Chicago Architecture Tour

Weave through the skyscrapers that make up Chicago's iconic skylines in company of an expert
From US$325 privately
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Tour Details
3 hours
Product Type
  • Willis Tower - Sears
  • Monadnock Building
  • Chicago Cultural Center
  • Tribune Tower
Photos & Highlights
  • Learn about Chicago's architectural legacy, explore the interiors of these remarkable buildings
  • Led by an architecture historian or architect
Select a date
Tour Description
Do you know where the first skyscraper was built? Or, where is the world's largest Tiffany dome? Or, where is the tallest building ever designed by a woman? Yes, they are all in Chicago.

Chicago is one of the world's most important cities for architecture. This 3-hour tour takes you from the first pioneer skyscraper built in 1885 to the cutting-edge modern structures of today's skyline. 

Led by an expert architectural historian or architect, we will open the doors to these extraordinary buildings and immerse ourselves in the marble, iron, glass, and stainless steel. We will walk down their halls and amazing loobies, learn all the secrets, and discover all the hidden gems.

Our walk starts at the iconic Monadnock Building, which was - briefly - the world’s tallest office building. From here we will make our way through downtown Chicago, stopping to talk about famous landmarks like Alexander Calder's Red Flamingo in Federal Plaza and the towering Chicago Board of Trade Building.

As we leave this stylish giant behind us, we’ll glance up at Willis Tower, formerly known as Sears Tower and now Chicago's tallest skyscraper, and discuss the techniques behind its construction that have allowed it to reach such extraordinary heights. From here, our path may take numerous directions, such as entering the nineteenth-century Rookery and admiring its center court and majestic staircases renovated by Frank Lloyd Wright, or visiting Chase Tower and its neighboring glass and mosaic plaza, or the 1895 Marquette Building.

As we head north toward the river, we will enter the Chicago Cultural Center, once Chicago’s first Public Library, to admire its dazzling Tiffany Dome, the largest in the world. We will end our walk at the Michigan Avenue Bridge, where we will discuss iconic structures like the Tribune Tower, Marina Towers, and the Wrigley Building, which represent Chicago's architectural greatness.

  • You want a private guide just for yourself and your party.
  • You're seeking more than just the average tours that offer views from the outside; you crave the opportunity to step inside these buildings and discover all the hidden gems firsthand.
  • Whether you're an expert in architecture or completely new to the subject, you want to deepen your knowledge and bring home unforgettable curiosities about Chicago's unique skyline.

  • Willis Tower - Sears
  • Monadnock Building
  • Chicago Cultural Center
  • Chicago Board of Trade Building
  • The Rookery


This tour does not include any tickets, but there may be nominal site entrance costs or other fees. It is a good idea to have some cash on hand for these.

Additional Trip-Planning Resources

  • For more information on planning your travels to Chicago, take a read through our Context Stories.
  • If you are looking to learn more about Chicago prior to a visit, check out our online lectures at Context Learning.

Will I see all of the major monuments on this tour?
Chicago is a large city with a generous amount of famous landmarks. As many of these buildings serve as offices or residences, occasional closures for renovations or private events may occur. Your expert will discuss what the best route is for you and your party at the beginning of the tour, and should any closures arise, they will take you to an alternative route.

Are we going to take a boat on this tour?
No, we are not going to take a boat. We believe that physically entering these iconic buildings offers a far superior means of gaining knowledge about them.

Where does this tour start and where does it end?
The tour begins in the Loop area, at the Monadnock Building, and ends near Michigan Avenue Bridge. Your guide can point you in the right direction for a public transport stop if necessary.

What if it’s raining?
Tours operate rain or shine, but in the case of inclement weather, your expert will modify the tour so more time is spent indoors. It never hurts to have an umbrella on hand.

Is this tour wheelchair-friendly?
We cover approximately 2.5 miles on this tour, and while some sites may not be fully accessible to wheelchairs, your guide can adjust the itinerary to ensure you have a comprehensive experience. Feel free to reach out to us with any inquiries or concerns.

Book with confidence — see Context's flexible cancellation policy here.

Where You'll Start
(4.85) 31 Reviews

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Sally's knowledge and passion for Chicago history and characters and its buildings is amazing and makes for a wonderful tour. Thank you.
William was a fantastic guide. His knowledge of Chicago’s architecture was second to none. I loved the level of detail he explained in a variety of buildings both old and modern. Hugely informative.
This was our fifth Context tour and we've come to have very high expectations of them. Colm did not disappoint! He was friendly, incredibly knowledgeable, and all around fantastic. It made our weekend.