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The 17 best architecture tours of Chicago

Discover Art Deco skyscrapers, modern marvels and Frank Lloyd Wright–designed homes on these architecture tours of Chicago

Written by
Lindsay Eanet

Even if you're a longtime local, there's something special about taking in the city's architecture on foot or from the water with the help of an expert. From glass and steel castles to ornate Art Deco buildings to street art and cultural landmarks in our neighborhoods, there's a reason these tours are among the best attractions in Chicago. Nerd out over the design, engineering and construction behind the most beautiful buildings in Chicago on guided walks, bus rides and boat tours. First-time visitors will be happy to know that these architecture tours double as sightseeing walks of the best Chicago attractions—you might even be able to snap a few Instagrams along the way. Here's a few of our favorite tours that are equally engaging for tourists and Chicago lifers. 

RECOMMENDED: Check out the full guide to the best Chicago tours

Architecture tours of Chicago

For a comprehensive overview of Chicago’s skyline, there’s no better vantage point than aboard Chicago's First Lady. You’ll spy more than 50 architecturally significant buildings, from the Wrigley Building to newcomers like the St. Regis. An expert guide will give you the lowdown on Chicago’s rise from the Great Fire of 1871, the advent of balloon-frame construction and other crucial moments in the city’s history. Choose to cruise by day or watch the city light up with an evening option. $52


Want to check out Chicago's architecture but short on time? Try this 90-minute "Greatest Hits" walking tour from the Chicago Architecture Foundation, which offers an informative, fast-paced introduction to key landmarks. The tour includes stops at more than a dozen buildings, including the Chicago Theatre, Aqua Tower, Willis (Sears) Tower, the Wrigley Building and the Art Institute of Chicago. Make sure to bring something to take notes! $30


One of the coolest aspects of Chicago architecture is that it's always evolving, with new landmarks continuing to shape our skyline. This 90-minute tour from the Chicago Architecture Foundation is all about what's new in Chicago, taking guests to buildings like 462 N. Park and the St. Regis and discussing their impact on the city's changing built environment and economy. $30

These tours, led by experts dedicated to preserving and educating about the work of Chicagoland's most famous architect, are definitely not cheap, but a must for Frank Lloyd Wright superfans. (Frankenstans?) The "Wright Around Chicago" includes stops at the gorgeous Rookery Building and Wright's home and studio in Oak Park, while the "Wright Along the Lake" tour includes a visit to the exquisite 1915 Emil Bach House. Oh, and lunch and a prosecco toast are included. $195


If you're traveling on a budget, you can still get an excellent overview of Chicago's architecture thanks to Free Tours By Foot's pay-what-you-can two-hour walking tours. These volunteer-led tours take you to key landmarks like Cloud Gate, Marina City, the Leo Burnett Building and works by Frank Lloyd Wright, Louis Sullivan and Mies van der Rohe. 

Take a trip back to the Roaring Twenties with this tour, which takes you through the history of many iconic Chicago buildings. Choose from the Loop route, which includes One North LaSalle and the towering Board of Trade, or the Riverfront route for the gold-topped Carbide and Carbon building and the Holabird and Root-designed 333 N. Wacker Drive. Admire the geometric shapes, vibrant colors and sophisticated elegance that Art Deco construction is so well known for on these two-hour walking tours. $30


Although these tours (which are created and by civic historian and TikTok star Shermann "Dilla" Thomas) aren't exclusively architecture-focused, the built environment plays a huge role in their explorations of the history, contributions and legacies of South Side neighborhoods like Roseland and Back of the Yards. And from Bronzeville's beautiful boulevards to Pullman's historic workers' homes, there's plenty for architecture buffs to explore on these important tours. 

Live in Chicago and feel like you've done all the downtown-centric architecture tours? Maybe it's time to give Chicago for Chicagoans a go. The tours, developed for locals by locals, are designed to build community and give Chicago natives a stronger appreciation for their neighborhoods and neighbors. Enjoy walking tours and fun scavenger hunts of Albany Park, Chinatown, Pilsen, Beverly and more—and the tours frequently end at local restaurants if all that walking works up an appetite.


If you prefer sleek metal and glass designs to ornate Gothic architecture, you’ll want to book a spot on this two-hour walking tour of the city’s most famous modern buildings. Peep minimalist designs from Ludwig Mies van der Rohe, admire the Beaux-Arts beauty of the Harold Washington Library and ogle the chic contemporary look of One South Dearborn, among others. $30

The announcement that the World’s Columbian Exhibition of 1893 would be held in Chicago spurred an explosion of new construction. Beaux-Arts buildings sprung up all over Jackson Park and the South Side—so many sparkly new buildings, in fact, that the area earned the nickname “White City.” More than 125 years later, visitors can still see the architectural impact of the fair on the city. This tour includes a visit to Jackson Park's Garden of the Phoenix and the Skylanding sculpture by Yoko Ono. $30


Don’t want to share your tour guide with a group? Reserve a private tour to spend an entire afternoon exploring the city’s most impressive buildings. You’ll stop at everything from Willis Tower to Gothic facades on the Magnificent Mile to Frank Lloyd Wright homes in Oak Park. Did we mention you’ll be chauffeured from stop to stop in a luxury town car or SUV, too? $930.60

As in so many industries, women’s contributions to the world of architecture have only recently begun to get their moment in the sun. Discover some of the female architects leaving their mark on Chicago’s skyline on this 45-minute virtual tour led by an expert from the Chicago Architecture Foundation, featuring sites like the Aqua Tower and Equitable Building. Who built the world? Girls! $8 for the public, free for members


What's so exciting about brick? Common brick built much of Chicago, and this tour, created by local teacher Will Quam, takes you around neighborhoods like Logan Square, Hyde Park and Bronzeville to show how the built environment created our interesting and beautiful city. After marveling at churches and greystones and Gilded Age mansions, you'll find yourself taking a second, more appreciative look at the world around you. $12–19

This 2-hour neighborhood-centric Chicago Architecture Foundation tour takes you through historic Midway Park, shows you works by prominent local architects including Frederick Schock, William Drummond and Dwight Perkins and gives you an opportunity to marvel at the neighborhood's grand Queen Anne and Prairie homes. During the tour, you'll also hear from Austin residents about their efforts to revitalize the neighborhood following decades of disinvestment and racist housing practices.


Explore the cultural influence and impact of the many immigrant groups who have called Pilsen home and the intersection of art and architecture on this tour from the Chicago Architecture Foundation. On this two-hour tour, you'll visit residential, commercial, residential and cultural sites, from the 18th Street Pink Line station's murals to the Sokols, century-old Czech athletic clubs. $30

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