Chicago Architecture Tours: Best Architecture Tours in the Windy City

on October 5, 2019

Chicago’s architecture is legendary. In fact, you can’t visit without taking in just a little of the city’s architecture. (Well, you could try; but it wouldn’t be easy). The best way to see as many buildings and styles as possible is to take a few Chicago architecture tours. We happen to think these four tours offer a great overview of the city’s architectural history.


Before we get into the tours, note that the Chicago Architecture Center (CAC) is a nonprofit organization that is dedicated to preserving Chicago’s architectural history. In other words, these guys know what they’re talking about.

You can jump on one of their walking or boat tours to learn about the city’s architectural history from one of their knowledgeable tour guides. The best part about these tours is that guides are equally informative and engaging. Minds, blown.

Tours run by CAC include:

  • Historic Treasures of Chicago’s Golden Age
  • Illinois Center Parkway
  • Historic Skyscrapers
  • Art Deco Skyscrapers: The Riverfront


One of the most iconic ways to see Chicago architecture is by boat. When it comes to the Second City, a river runs through it — and by boat happens to be one of the best ways to really get between the impressive buildings. Also, you can just see some buildings better by boat than by land.

Shoreline Sightseeing offers some of the most popular architecture tours in Chicago, including the ever-popular classic architecture tour and the lake tour.


Check out 50 skyscrapers from the comfort of your boat seat on this popular architecture tour. You’ll become acquainted with the Chicago River’s three branches while learning about Chicago’s architecture and history on this 90-minute tour.

They even hand out free cookies and Starbucks coffee.


If you’re the type of person who likes to paddle their own canoe, you can always take a kayak tour of the Chicago River.

Water Riders offers an architecture tour that’ll get you close to all the big-deal buildings in Chicago — and it’s a great workout. If you happen to be in Chicago around Halloween, they do a pretty cool haunted river tour, too.


What’s better than an architecture tour? A beer tour with an architecture slant! All our tour guides are super excited to talk about architecture with our guests. After all, architecture is one of Chicago’s most iconic characteristics.

Want to see some classic Chicago skyline? Check out our Sin & Suds Tour. You’ll see some pretty iconic Loop sights while sharing pints of beer with your fellow travelers.

Most of the other tour companies on this list only run tours between April and November (because, Windy City winters and all). Yet, we run weather-appropriate (think: as warm and cozy as possible) tours all-year long. Because we’ve got our beer jackets on, too.


If you want to just get out of your hotel room ASAP, you could always enjoy the city’s impressive structures on your own. Many of the tours on this list will take you through these neighborhoods. Yet, feel free to appreciate a few buildings on your own, too.

Chicago Architecture Center

Yes, the same organization that brings you one of the best tours on this list also runs a beautiful museum that you can visit. The exhibits focus on Chicago’s impressive architectural history, so visit this spot before heading out on a tour.

The center also runs family programs that help up-and-coming FLWs discover their love of architecture. These programs are designed for little architects in training, ages 3 through 5.

You can also learn about architecture preservation and enjoy the center’s impressive glass and iron architecture.

Chicago’s Riverwalk

Some of the most impressive architecture in Chicago can be found along the Chicago River. If you don’t want to board a vessel to gaze upon gorgeous facades, you can always enjoy them equally on land.

Just head to the Riverwalk. This effort of revitalization is a piece of art in itself. But it’s the buildings themselves that are the stars along this 3.4-mile trail.

From here, you can see the following structures:

  • Tribune Tower
  • Wrigley Building
  • The Mart
  • Apple Store
  • AMA Building
  • Jewelers Building

You’ll also get glimpses of some of the most impressive modern skyscrapers in the city!

Millennium Park

Yes, Chicago’s most famous park is also one of the best spots to check out its architecture. Some of the most famous nearby buildings include:

  • Aon Center
  • Monroe Building
  • Wrigley Building
  • Chicago Theatre
  • Rookery Building
  • Willis Tower

Nearby (in Grant Park) is the Art Institute of Chicago, which specializes in both art and architecture history.

Oak Park

If you’re a die-hard architecture fan, you’ll want to take a trip out to Oak Park, where you can see one of the most famous Frank Lloyd Wright structures, Frank Lloyd Wright Home and Studio.

This building is where FLW lived with his family in 1909 and is one of the most iconic structures created by the architect.

It has since been preserved and transformed into a museum. The foundation offers house walks of some of the architect’s most famous Chicago buildings.

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