The best 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. 

Cost: $54 for daytime cruises, $59 for evening cruises

You're certainly not short on great options to see Chicago's stunning architecture from the river. On Shoreline Sightseeing's signature 75-minute tour, you'll observe more than 40 landmarks, including Tribune Tower and Marina City. A knowledgeable guide shares the stories behind the architects, engineers, movers and shakers that gave us the nickname "City of the Big Shoulders."

Cost: $35-50

Detailing the 130 year history of the Chicago skyline, this tour along the Chicago River is nothing short of breathtaking. Equipped with a full bar on board, a climate-controlled lounge and expert tour guides, Wendella brings luxury to the touring experience.

Cost: $44 for adults, $20 for children. 

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!

Cost: $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 walking tour from the Chicago Architecture Center is all about what's new in Chicago, taking guests to buildings like 465 North Park and the St. Regis and discussing their impact on the city's changing built environment and economy.

Cost: $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. Oh, and a prosecco toast at the Rookery Building is included.

Cost: $225

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. 

Cost: pay-what-you-can

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.

Cost: $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.

Cost: $45

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.

Cost: $10-$20 (suggested donation)

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 towering Aon Center and ogle the unique look of Marina City, among others.

Cost: $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 Midway Plaissance

Cost: $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?

Cost: $880

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 90-minute tour led by an expert from the Chicago Architecture Center, featuring sites like the Aqua Tower and Equitable Building. Who built the world? Girls!

Cost: $30

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 Center. 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.

Cost: $30

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.

Cost: $25

This two-hour, neighborhood-centric Chicago Architecture Center 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.

Cost: $30

Of course we had to include the Segway tours! Strut around the city in style aboard these two-wheeled marvels of tour-guide technology. From museum campus to an "insider" tour that reveals the lesser-known parts of downtown, these tours are a great way to cover a lot of ground without any of exhaustion. See the lakefront, parks and skyline like never before. 

Cost: $65-$72