Just about every city lauds its buildings but none that I’ve visited fetes them like Chicago does. And for good reason. This city was destined for architectural greatness starting with the “Great Rebuilding” that began after the Chicago Fire of 1871. It’s impossible to go to Chicago and not be entranced by its buildings and public spaces. At least part of every visit must focus on architecture.

From group tours to individual guides, on foot or by boat, there are many ways to explore Chicago architecture. Before leaving home decide how you’ll explore this city. Consider the options below but also check out the Chicago Architecture Foundation’s website for events that may be going on when you’re there. And visit the Chicago Greeter site to book a volunteer greeter who will introduce you to their city with the unique passion of a local–many languages and themes, including architecture, are offered.

Now, three ways to explore the buildings of Chicago.

Looking at Chicago's skyline through the front window of the architectural boat tour.

Looking at Chicago’s skyline through the front window of the architectural boat tour.

Chicago’s architecture by boat

The Chicago Architecture Foundation (CAF) runs cruises up and back down the Chicago River with CAF certified guides providing lots of commentary and architectural information along the way. It is the only organization authorized to do so. From the boat you’ll get quite a different perspective on the city than you get from the street. This tour takes you through the downtown past both iconic Chicago buildings and newer ones like the Trump Tower and into areas that have become residential through gentrification. You’ll learn about the history of Chicago as it is intensely intertwined with the city’s architecture. This tour is a great option to start your visit to Chicago.

Chicago’s architecture on foot

Downtown Chicago is laid out in an easily navigable grid pattern. It’s natural to explore this area, called the Loop, on foot. Start your tour at the Visitor Information Center that is located in the Chicago Cultural Center at 78 East Washington Street. Pick up a map and information on your specific interests. Since you’re there, find out what free cultural events will be going on at the Center while you’re in town.

Now I’m not an architectural nerd so the technology behind a structure doesn’t impress me. However, the feel–the experience–of a building does. From my perspective, here are three highlights you won’t want to miss:

  • Willis Tower at 233 South Wacker Drive is the tallest building in the western hemisphere. It offers 360-degree views of Chicago from The Ledge, a clear glass box that extends over four feet beyond the building’s Skydeck. (This building was formerly known as the Sears Tower.)
  • Aqua Tower at 225 North Columbus Drived is a multi-use building containing a hotel, apartments, condominiums, parking, offices, and one of Chicago’s largest green roofs. Located near the shores of Lake Michigan, its terraces are all unique and formed like undulating waves making this water-inspired building feel as much like public art as much as it is architecture.
  • The Wrigley Building at 400 North Michigan Ave. is located across from the Tribune Tower on Chicago’s Magnificent Mile. With its white terra-cotta cladding and well-proportioned architecture from the 1920s it has come to symbolize Chicago.
Architectural detail at Frank Lloyd Wright's Home & Studio.

Architectural detail at Frank Lloyd Wright’s Home and Studio in Oak Park.

Chicago’s architecture by public transit

Another option for the Downtown Loop is to take the “L” (elevated train) that circles the loop. From the brown, orange, or pink lines, and preferably from the first car, you’ll see many of the city’s major landmark buildings.

There is more architecture outside the city centre that is easily accessible by public transit. There are a few Frank Lloyd Wright buildings and others from the Prairie School that influenced Wright. Seeing Wright’s Home and Studio needs to be a priority. Located five pleasant blocks from the Oak Park Metra station, it’s easy to get to. The tour is well worth it as the docents are excellent at explaining the background to architectural decisions Wright made as well as giving some insight into family life. You can learn more about the man’s presence in Chicago from the Frank Lloyd Wright Trust.

The options for exploring architecture in Chicago are endless.
Do you have a favourite building to recommend?
Do you have a favourite city for exploring architecture?