9 Best Chicago Architecture Tours To Explore (TOP RATED)

Looking for the best Chicago architecture tours? Well, you’re in the right place!

Welcome to Chicago, the birthplace of the modern skyscraper and a haven for architecture lovers. From historic landmarks to futuristic designs, the city’s skyline tells a rich story that spans centuries.

But how do you truly experience the grandeur of these architectural marvels? 

By exploring them through tailored tours. Lace-up your walking shoes or hop on a boat, and allow us to guide you to the Best Chicago Architecture Tours that offer not just a view but an insight into the essence of the Windy City!

This article contains affiliate links where we may get a small commission if you click on the link and purchase. No extra cost is added to you.

1. Chicago Architecture River Cruise

Step aboard the Chicago Architecture River Cruise for an unforgettable educational journey. This is a 75-minute boat ride that will show you a river perspective of Chicago’s architecture.

It showcases a variety of architecture with towering buildings made from the 1890s to the modern day, like the Wrigley Building, Willis Tower or formerly known as Sears Tower, and many more. 

Plus, you’ll be accompanied by an entertaining and knowledgeable local guide eager to share Chicago’s beauty from a different perspective, making it an excellent tour for those who love architecture and those new to the city!

2. Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

Discover the hidden architectural gems of Chicago with the Dazzling Interiors™ of the Loop walking tour. This 2-hour tour takes you inside some of the most beautifully designed buildings in the city.

You’ll explore the stunning interiors of structures like the Chicago Cultural Center, its breathtaking Tiffany dome, and the Marquette Building, with its exquisite mosaic murals. 

Accompanied by an expert guide who cares about the city and its building, sharing the history of these must-visit wonders, the architects who designed them, and the periods these buildings came from.

This is a fantastic way to delve deeper into Chicago’s rich architectural heritage by letting you experience the city from a local’s POV.

3. Private Chicago Architecture Tour

Dive into the rich architectural world of Chicago with the Private Chicago Architecture Tour. It takes approximately 3 hours, and you will be led by a passionate and knowledgeable guide who will show you the views of Chicago’s most famous landmarks and beautiful interior designs. 

Marvel at historic buildings such as the Sears Tower, historic brownstones, and even the homes at Oak Park – made by none other than Frank Lloyd Wright, one of the most renowned architects in the world!

And you’ll be traveling on chauffeured Luxury Transportation for maximum comfort! This is a must for those who want to learn more about the masterpieces of the renowned architect, who designed 1,000 structures in 70 years and is an inspiration for architecture.

4. Chicago Architecture Walking Tour: The Underground Pedway & Secrets of the Loop

Uncover the hidden side of Chicago with the Chicago Architecture Walking Tour: The Underground Pedway and Secret of the Loops. This takes approximately 2 hours and will show you a different side of Chicago that even lifelong locals sometimes miss.

Take a stride at the Loop, a lively neighborhood full of history and architectural landmarks, such as the Chicago Pedway, Picasso Statue, Millenium Park, and more.

There’s no better way to sightsee the city than expand your knowledge on its state-of-the-art architecture! 

Imagine viewing stunning buildings inside and out while learning its history and secrets from a local guide — simply amazing!

5. Chicago Walking Tour: Tiffany Treasures

Discover the fascinating world of Tiffany’s incredible art glass on this special walking tour in Chicago. 

The itinerary takes you to three buildings with awe-inspiring glasswork created by the Tiffany Glass and Decorating Company, including the Chicago Cultural Center, Marquette Building, and Macy’s on State Street!

The stunning art and historical background make this tour an ideal choice for fans of architecture and history.

6. Chicago Architecture & Highlights with Local Treat – Small Group Walking Tour

Discover Downtown Chicago’s architecture and history by embarking on the Chicago Architecture & Highlights tour, including a local treat.

This tour, which lasts approximately 2 hours and 30 minutes, provides flexibility in choosing your preferred time. 

You’ll be on foot, exploring popular sites such as the Picasso Statue, Chicago Riverwalk, Magnificent Mile, and Millennium Park.

Your guide will passionately explain the city’s evolution and the architects who defined its skyline. The tour also includes a stop at a beloved local spot for a snack, seamlessly combining city sightseeing with culinary exploration.

7. Frank Lloyd Wright Robie House

Experience the architectural genius of Frank Lloyd Wright with a tour of the globally recognized Robie House. During this approximately 1-hour tour, a guide will provide detailed insights into both the exterior and interior of the building, one of Chicago’s architectural pride. 

The Robie House is emblematic of Wright’s Prairie style, marked by its horizontal lines, flat roofs with wide eaves, and windows arranged in horizontal bands.

The tour offers a deep dive into Wright’s innovative design principles, especially his concept of “organic architecture”, which promotes harmony between human habitation and the environment. 

A tour of the Robie House is not just a sightseeing activity—it’s a journey into the creative vision of a master architect!

8. Chicago Walking Tour: Historic Skyscrapers

Journey back in time and admire the architectural titans of yesteryears with the Historic Skyscrapers Walking Tour in Chicago.

This tour takes you around the Loop, showcasing early skyscrapers that shaped the impressive Chicago skyline.

You’ll appreciate the Chicago Board of Trade building, Monadnock Building, among other structures from the late 19th to early 20th centuries, while a knowledgeable guide from the Chicago Architecture Foundation shares insights into their creators.

This tour offers a rich perspective on the city, its rich history, and the architects who designed and sculpted its current form.

9. Chicago Walking Tour: Connecting Past and Present

Immerse yourself in Chicago’s rich architectural heritage with the Chicago Walking Tour: Bridging History and Modernity. Lasting about 1 hour and 45 minutes, this tour offers a wealth of knowledge from an expert in architectural history. 

You’ll learn about the city’s past, the varied building styles, their influences, and even get to explore the interiors of some buildings. The guide’s detailed commentary will deepen your understanding of the city, especially the awe-inspiring Chicago skyline.

Ideal for history enthusiasts, architecture fans, or anyone interested in the city, this tour is a must-experience in Chicago.

There you go! Chicago’s majestic skyscrapers have shaped its iconic skyline, and architectural tours provide an unparalleled way to explore these towering structures.

Looking for more activities to explore the city? Check out the best food tours in Chicago here!