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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

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

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Architecture tours of Chicago

Chicago Architecture Foundation River Cruise

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

Shoreline Sightseeing Architecture River Tour

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." $43-47

Chicago's Original Architecture River Tour

Travel the Chicago River in style with a bartender, an entertaining tour guide and killer views as you explore the city's architecture on all three main branches of the Chicago river. A 45-minute version is also available. $42

Must-See Chicago

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

Frank Lloyd Wright Trust Bus Tours

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

Free Tours By Foot's Architecture Tour

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. 

Chicago Walking Tour: Art Deco Skyscrapers

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

Chicago Mahogany Tours

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. 

Chicago For Chicagoans

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.

Chicago Walking Tour: Modern Architecture

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

White City Revisited

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

Private Chicago Architecture Tour

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

Women in Chicago Architecture

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

Brick of Chicago

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

Historic Austin

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.

Walk Pilsen

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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Riverwalk West

This tour helps you discover the western portion of the Riverwalk, starting at the Vietnam Memorial near State Street. As we walk to Lake Street, hear how this linear park—called Chicago’s new coastline by some—has become a magnet for outdoor recreation.

This tour visits the six "rooms" or locations where people can walk, sit, eat and drink while enjoying the view of passing boats and kayaks. See magnificent and iconic buildings along the way, including Merchandise Mart , site of the unique Art on the Mart display. Understand how the Riverwalk was built—and why.

• Many tours sell out. To guarantee your space advance reservations are strongly recommended.
• Your safety is our priority. The itinerary of this tour may be altered in accordance with health and safety policies and considerations.
• The tour ends at the Riverbank “room” between Franklin and Lake Streets on the Riverwalk level.
• Ticket price includes entrance to the Chicago Architecture Center within 7 days of your tour. View the CAC's hours .

Photos From This Tour

Upcoming Riverwalk West Tours

Wednesday jun 12.

• 10:30am Buy Tickets

Thursday Jul 4

Tuesday jul 16.

• 5:30pm Buy Tickets

Tuesday Jul 23

Monday aug 5, wednesday aug 14, highlights of this tour.

Chicago Riverwalk

1 w. lower wacker drive.

Strolling along Chicago’s beautiful Riverwalk, it’s hard to imagine just how much things have changed…

Skidmore, Owings & Merrill

Architect/firm.

Skidmore, Owings & Merrill (SOM) was founded in 1936 by Louis Skidmore and Nathaniel Owings. Partner…

trunnion bascule bridge

trunnion is a French word for "stump" or pivot point; bascule is a French word for "see-saw"; a trunnion…

Marina City

300 n. state st..

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Merchandise Mart

222 w. merchandise mart plaza.

Size has always mattered in the Midwest.

150 North Riverside

150 n. riverside.

Gravity-defying 150 North Riverside has already taken its rightful place among Chicago’s architectural…

a large vertical, concrete pier, cast in place and used in a foundation where the soil is unstable

London Guarantee Building

360 n. michigan ave..

Located where Fort Dearborn once stood, the London Guarantee & Accident Building is one of four structures…

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Chicago architecture tour: two-day itinerary

From Frank Lloyd Wright’s Prairie School to skyscraper cool, you’ll find architecture that’s just your style in Chicago. This self-guided architecture tour covers some of the city’s most iconic buildings throughout the city, from historic landmarks to ground-breaking modern wonders.

Chicago architecture tour day one

Morning and afternoon: Loop architectural highlights

Willis Tower Willis Tower (formerly the Sears Tower) may be one of the world’s tallest buildings, but that’s not the only amazing thing about it. Head up to the 103rd floor and be wowed by The Ledge at Skydeck , an enclosed glass box that extends roughly 4 feet from the building facade, 1,353 feet up. You’re literally walking on air — with your heart pounding.

The Rookery The Rookery, originally designed by Burnham and Root, is where you’ll find one of the city’s most photographed interiors — Frank Lloyd Wright’s two-story skylight lobby. It’s airy, industrial, and picturesque all in one go. Start snapping and sharing.

Monadnock Block Architecture buffs will love the fact that this Burnham and Root building is the last of Chicago’s great masonry skyscrapers. Note for the buildings north and south facades represent two very different styles: a more modern and minimalist look vs. a traditionally ornamented display designed by Holabird & Roche two years after the first half.

Aqua Tower Take a moment to gaze in awe at the Aqua Tower — it’s as much outdoor sculpture as it is architecture. This shimmering high rise features undulating outdoor terraces that mimic the movement of Lake Michigan’s waters. It’s the second-tallest building in the world designed by a woman-owned architectural firm, Studio Gang Architects, and it’s home to the Radisson Blu Aqua Hotel .

The St. Regis Chicago A true feat of engineering, the stunning St. Regis skyscraper rises from the banks of the Chicago River. Jeanne Gang is set to beat her own record with the Vista Tower, making it the third tallest building in Chicago and the tallest structure in the world designed by a woman. Note how the sleek design complements the look of the nearby Aqua tower.

Chicago Architecture Center You get double the architectural history at One Illinois Center. Not only was it designed by Ludwig Mies van der Rohe, but it’s also the location of the Chicago Architecture Center, the perfect starting point for your discovery of Chicago’s downtown architecture. Enter through the main doors and you’ll have your pick of over 85 walking, bus, and boat tours.

Wander up one level for the main attraction, Building Tall in the Skyscraper Gallery. Towering scale models of the world’s most famous skyscrapers frame views through massive windows onto, well, some of the world’s most famous skyscrapers. The center is located above the Chicago Riverwalk , with a dedicated dock for the center’s signature Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady .

Afternoon and evening: The Magnificent Mile

360CHICAGO Just about everybody recognizes 875 N. Michigan Ave., formerly the John Hancock Center. But what you may not know is it’s home to an amazing 94th-floor observation deck. TILT at 360 CHICAGO is a hydraulic platform that literally tilts you out and over The Magnificent Mile , at a height of 1,030 feet. After your adrenaline rush, take an elevator one floor up to the Signature Room at the 95th for fine dining, delicious cocktails, and even more stunning views.

Historic Water Tower With a detailed Gothic Revival facade, Historic Water Tower bursts with charm. It was built as part of Chicago’s municipal water system, originally housing a 135-foot iron standpipe used to regulate water pressure, and one of the few city structures to survive the Great Chicago Fire. Today, it’s the City Gallery at Historic Water Tower , and the place to go for free rotating art exhibits. The original pumping station, another survivor of the fire, is just across the street.

Tribune Tower The Tribune Tower is a striking Gothic Revival tower that formerly housed the Chicago Tribune newspaper. Made of Indiana limestone, the design incorporates Art Deco, Medieval, and French cathedral inspired details.

The building’s first story walls are embedded with roughly 150 fragments from the world’s most important historic buildings and sites, including the the Berlin Wall, the Winter Palace in Beijing, Westminster Abbey in London, the Great Pyramid in Giza, and the Parthenon in Athens.

Wrigley Building The Wrigley Building’s dazzling white terra-cotta exterior was modeled after the Giralda tower in Spain — with some French Renaissance details thrown in.

Next, head down to the Chicago Riverwalk . You’ll find scenic coves, restaurants, bars, public art, and a whole lot more waiting for you. For the perfect end to your day, hop on an evening architecture tour to learn more about the city’s riverfront structures and get a whole new view of these iconic buildings.

Chicago architecture tour day 2

Morning: Frank Lloyd Wright in Oak Park

Just eight miles west of Chicago, Oak Park is lucky enough to have the largest collection of Frank Lloyd Wright-designed buildings in the world. A quick ride on the Green line ‘L’ train will drop you off in downtown Oak Park, the perfect spot to start exploring Wright’s local legacy. While many are private residences, the Frank Lloyd Wright Trust offers interior tours of some of the greats. Here are two you shouldn’t miss.

Frank Lloyd Wright Home and Studio It’s not often that you get a glimpse inside a legendary architect’s home and studio — let alone the birthplace of the Prairie School of architecture. But that’s exactly the chance you’ll get when you visit this groundbreaking residence.

Unity Temple Did you know that Frank Lloyd Wright also took on commercial commissions? Well, Oak Park’s Unity Temple was the first. This was also one of the first times exposed concrete was used on a public building, ushering in a whole new era in architectural design. On the inside, though, this “little jewel box,” as Wright called it, is full of natural light and a sense of airiness.

Tip : If you’re a fan of Wright’s work, you can see more of his iconic works throughout Chicago. Head to the Hyde Park neighborhood for a tour of Robie House , a UNESCO World Heritage site and one of the best known examples of Prairie style architecture. In the lakefront Rogers Park neighborhoods, the Emil Bach house is open for both tours and overnight stays.

Afternoon: Prairie Avenue

Head back to Chicago for an afternoon in one of the city’s most scenic historic districts. If you were one of the Chicago elite in the late 1800s, then the Prairie Avenue District in the South Loop was where you made your home. Hence the area’s nickname, “Millionaire’s Row.”

Must-sees here include:

Clarke House & Museum Let the experts tell you all about Chicago’s oldest home on a free docent-led tour. You’ll get a glimpse of frontier life, an eyeful of beautiful period furniture and decorative arts, and views onto the lovely Chicago Women’s Park and Gardens right next door.

Glessner House The neighbors were just a little upset when fortress-like Glessner House made its appearance in 1887. Today, it’s loved for its architectural genius and progressive design. Take a guided tour to discover a secret central courtyard, warm oak-paneled interiors, a grand staircase, stately fireplaces, and an impressive collection of antique furniture and decorative arts.

Late afternoon/evening: River North gems

Downtown Chicago’s River North neighborhood is jam-packed with significant skyscrapers and reminders of Chicago’s Gilded Age. Spend the late afternoon touring historic buildings and stunning interiors, and then wrap up the day with a little public art.

Richard H. Driehaus Museum Welcome to the “Marble Palace,” with grand staircases, decorative arts, imposing fireplaces, and antique furnishings as far as the eye can see. The Driehaus Museum hosts rotating exhibits and fun special events, including whodunnits and afternoon teas. It’s a beautiful glimpse into Chicago’s Gilded Age, and a definite must-see.

Marina City When you see two giant corn cobs reaching for the sky, you know you’ve arrived at Marina City.

When it opened in 1962, it was the tallest residential building and tallest concrete structure in the world. The unique structure was envisioned as a “city within a city”, with residential space, a theatre, parking for cars and boats, and plenty of retail.

Check out the marina level, where you can rent a small electric boat and explore the Chicago River. And for great live entertainment, walk over to House of Blues right next door.

theMART When it opened in 1930, theMART (originally named Merchandise Mart) held the record as the largest building in the world. It was so big, it had its very own ZIP code up until 2008.

The space originally served as Marshall Field’s wholesale warehouse, where retailers could buy stock. In 1945, the building was bought by the Kennedy family, who owned it for more than three decades.

Today, theMART is breaking another record — for the largest digital art projection on the planet. Art on theMART covers 2.5 acres (the equivalent of two football fields) of theMART’s massive Art Deco façade. End your architecture tour by grabbing a spot on the Riverwalk and watching the colorful projections light up the night.

Keep exploring : Mark your calendars for these can’t-miss architecture events in Chicago .

From this article

Tours & Attractions

Willis tower.

Skydeck Chicago

Rookery Building

Accommodations

Radisson blu aqua hotel, chicago.

Chicago Architecture Center

Chicago Riverwalk

360 CHICAGO Observation Deck

The Magnificent Mile

Historic Water Tower

City Gallery at the Historic Water Tower

Clarke-Ford House

Chicago’s Women’s Park and Gardens

Glessner House

Driehaus Museum

River North

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Our walking tours showcase architectural interiors — the best way to enjoy Chicago in any weather!

All of our regular public tours are 2 hours long, explore several interior spaces (unless otherwise noted), and cover between 1.25 and 1.75 miles at a leisurely pace. Private tours are always available, and are 100% customizable in terms of content and length.

We run multiple tour times for our regular tour routes each week, with special seasonal tour offerings available throughout the year.

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Chicago Walking Tours

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Loop and millennium park highlights.

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Free Tours by Foot is pleased to present the best pay-what-you-like guided Chicago walking tours. 

These interesting and informative sightseeing city tours will take you through many of the Windy City's most famous neighborhoods.

Everyone should be permitted to take a guided tour for a price they feel it was worth or what they could afford – even free!  

Pay-what-you-like tours are tours for every budget.  

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CHICAGO WALKING TOURS

We provide a platform for local, freelance tour guides to lead walking tours as well as ghost and architecture tours at no upfront cost, so that you may enjoy a worry-free quality sightseeing experience.

Walking tours are our forte, and we offer a number of daily and weekly pay-what-you-like walking tours of Chicago as well as completely free self-guided options.

You could browse the tours that we have by clicking the links below, by scrolling our public calendar (also below) or it just might be best to go directly to our  booking page . 

There’s no cost to book our walking tours. 

We have roughly 1000 reviews with a rating of  5 out of 5 stars and with 97% of reviewers rating us as very good or excellent.

We are so well-reviewed, yet TripAdvisor seems to hide us from you (probably because they can’t sell our tours for commission).   Read the reviews  for yourself.  

Our premiere Chicago walking tours are great day or night and serve as introductions to the city, Chicago history and cover the many of the main tourist attractions.   

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Our Regularly Scheduled Tours

• The Birth of the Skyscraper:  Architecture Tour is a great way to discover and appreciate the incredible landscape of buildings in Chicago and it ends in Grant Park near the famed Buckingham Fountain.
• The  Riverwalk and Chicago History Tour follows the path of the Chicago River and focuses on the history of Chicago, the Chicago Flag, and the beautiful buildings that line the river.
• North Loop and Millennium Park Tour , which covers a great portion of Chicago’s downtown Loop neighborhood, public art, and ends in Millennium Park.
• Our  Chicago Ghost Tour -Haunting History is for folks who love haunting history and creepy tales of the dark side of the White City.
• On The Magnificent Mile Tour , you will discover fun Chicago facts like the history of deep dish pizza while exploring our most popular downtown area.

Weekly Tours

• Our  Gold Coast Tour  meanders through the history of high society where you will be introduced to the glamorous residential neighborhood built around Lakeshore Drive.
• Explore Lincoln Park on our Lincoln Park and Gangster Tour to appreciate a unique neighborhood scattered with hidden history including tales of Chicago Gangsters.
• We also offer a West Loop tour which combines great storytelling for history buffs with great photo ops for those more in the “sightseeing” mood! 
• Get out of downtown and check out the Chicago Street Art on our Wicker Park Culture & Street Art tour.

Winter Tours

We offer tours year-round, even in Chicago's winter, but we take into account the need to be seasonably appropriate for walking tours. Check out our special Winter offers:

• In the winter, we offer a Pedway Tour that explores the indoor tunnels and paths to discover Chicago architecture and arts in a warmer way.
• There is also a  Winter Loop option where we will spend about half of the time outdoors looking up at the skyscrapers and the other half will be spent inside exquisite public buildings and lobbies.
• Our Winter Architecture Tour explores the unique landscape of buildings in the downtown area while also popping into many lovely lobbies for warmth!  This tour is abbreviated and adjusted for our Chicago winters.

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• Tour del North Loop y Millennium Park
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CHICAGO ARCHITECTURE TOURS

Many of our pay-what-you-like walking tours are architecture tours or architectural points are a large part of them.

These tours include:

• The Birth of the Skyscraper
• North Loop and Millennium Park Tour
• Riverwalk and Chicago History Tour
• The Magnificent Mile Tour
• West Loop Tour

In addition to our walking tours, there are other walking tour companies that offer excellent architecture tours.

Another popular option is to take an architectural boat cruise . There are even architectural tours by bus as well as Segway.

If you are on a budget or would just like to take things at your own pace, then consider one of our self-guided walks .

OTHER TOURS

In addition to walking tours, Chicago has bus, bike & boat tours. Read all about them...

• Best Chicago Architecture Tours
• Chicago Boat Tours Compared
• Hop on Hop off Chicago | Big Bus Tours vs. City Sightseeing Tours
• Chicago Ghost Tours | Haunted Tours in the Windy City
• Chicago Segway Tours
• Chicago Bike Rentals and Tours

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We also offer our guiding services for private groups, families, or school groups where we can guide you in the Loop, the South Side and anywhere else in Chicago.

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Chicago Riverwalk Architecture Walking Tour

A scenic walk through chicago’s iconic architecture.

• When 10 AM daily
• Duration 2 hours
• Meeting Point Next to the Tribune Tower, by the Jack Brickhouse Statue

$34 per adult

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• Meeting Point

• Explore the six distinct districts of the Riverwalk, each with its own name, urban landscape, and activities.
• Marvel at the Chicago River, the only river in the world that flows backwards.
• Discover the secrets hidden in facades of famous buildings.
• Learn about the “Founder of Chicago” who established a trading post that flourished into a world-class city.
• Admire striking modernist architecture that combines form, function, and history.

What you'll do

Surrounded by the hustle and bustle of the metropolis, you’ll stroll along the Chicago Riverwalk and marvel at the surrounding architecture and landmarks that have shaped this city and beyond. 

Our Chicago walking tour is led by expert guides with a passion for sharing this city’s history, architecture, and legacy with you.

You’ll hear the legend of the “Founder of Chicago,” learn why the Chicago River flows backwards, discover secrets hidden in plain sight within the facades of well-known buildings, and much more.

Whether you’re visiting Chicago for the first time or have lived here your whole life, this tour is a journey worth taking. Come explore Chicago’s Riverwalk and famous architecture with us, and you’ll be astonished at all you’ll discover

Tribune Tower

Gothic Revival design adorned with flying buttresses and Art Deco sculptures

Jean Baptiste Pointe DuSable Statue

Tribute to the “Founder of Chicago”

Wrigley Building

One of the most recognizable buildings in Chicago, featuring a Spanish-inspired clocktower

Chicago River 

Where the history of the city is written in water

A century in the planning and finally completed in the last decade

Jewelers Building

Once the tallest building in the world outside NYC

Marina City

A whole community in one development

Merchandise Mart

The largest building in the world when it opened in 1930, integrating elements from warehouses, department stores, and skyscrapers

333 West Wacker

At the exact spot where the three branches of the Chicago River meet

Plan your trip

Tour ending point.

This tour ends at the Riverwalk near Wacker Drive and Lake Street.

Refund policy

We offer a 100% refund up to 24 hours before the start time.

Our tour guide, Isabel, was a hoot and a half! So fun, so knowledgeable and so personable! Loved learning about the beautiful architecture!

Meeting point

Meet your guide next to the Tribune Tower by the Jack Brickhouse Statue at the front of Pioneer Court (near N. Michigan Ave).

How much walking is there?

This tour covers about a mile at a leisurely pace.

What is the rescheduling policy?

We understand plans change. We offer a 100% refund or the option to reschedule up to 24 hours prior to your tour start time. Within 24 hours of your tour, we would have incurred hard costs and therefore cannot allow rescheduling or cancellation without costs.

When should I get there?

Plan to show up 15 minutes early. The tour starts promptly, and you may not be able to catch up if you arrive late.

What if it rains?

Our tours run rain or shine. If there’s extreme weather and we have to cancel, you’ll get a full refund.

Are gratuities included?

Tips aren’t included but are always appreciated by our guides. If you think your guide did an outstanding job, a tip is a great way to show that.

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9 Great Chicago Architecture Tours

I f you're looking for the best Chicago architecture tours, you've found them here! As a local who has explored these tours on weekends, during staycations, or while showing visiting friends around Chicago, I can honestly say that this list shares the most unique and fun experiences.

The city has great options including the best architectural boat tours, helicopter tours, walking tours, and more.

If you have limited hours, take the Hop On/Hop Off bus tour in Chicago or visit the top Chicago attractions to get the most out of a short amount of time.

Architecture Tours You Should Try in Chicago

Chicago architecture cruise.

Check rates for Chicago Architecture Cruise

If you love touring on water, then this cruise is for you. I've taken this cruise several times while showing friends the city and they loved it too.

On this cruise, you will ride the Chicago River and see the city's famous architecture. You'll see the impressive flat skyline including over 40 famous buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building with audio narratives. The tour covers all three branches of the Chicago River.

Navy Pier Centennial Wheel Regular & Express

Check rates at Navy Pier Centennial Wheel

This is one of my favorite ways to see the city and the Chicago skyline. You circle only once, but the ride is super slow, and you'll have some great photo ops when you get to the top.

Navy Pier is among the most visited destinations in the world. It offers beautiful views from the wheel, and it's a must-do when in the area! Located right on the pier, you have spectacular views of the city's skyline, architecture, and waterfront.

45-Minute Private Helicopter Flight

Check rates at 45-Minute Private Helicopter Flight

I was scheduled to go on this flight but it was canceled due to bad weather. At least they are good at following safety protocol. Too bad that I missed this amazing experience by helicopter. From what I hear, you will get the best views of touring Chicago architecture, and the experience of flying amongst the clouds. 

Willis Tower Skydeck and The Ledge

Check rates for Willis Tower Skydeck and The Ledge

Having been on the Skydeck a couple of times, it never disappoints. What I didn't like much was that there is a limited time that you have to stand in the box. But if there were no supervision, the line would be from the street.

But here, you will have some of the most breathtaking views of Lake Michigan. You'll also see why home is to beautiful parks and cultural attractions such as the Adler Planetarium in Millennium and the Shedd Aquarium in Grant Park.

Look north to see Chicago's iconic skyscrapers and landmarks from Lincoln Park to the world-famous Wrigley Field.

Night Tour with Willis Tower Entry & Skyline Cruise

Check rates at Night Tour with Willis Tower Entry & Skyline Cruise

This tour is a wonderful way to spend the evening while touring in Chicago. You'll immerse yourself in one of the tallest architectural buildings in Chicago along with a Chicago boat tour. 

Experience the Windy City’s most popular attractions on this overnight tour. Watch the night light show of Buckingham Fountain. Cruise along the Chicago skyline and climb to the top of the iconic Willis Tower.

Big Bus Panoramic Sunset Tour with Live Guide

Check rates at Big Bus Open-Top Panoramic Night Tour

If this is your first visit to this city, this is a great way to tour Chicago , Illinois and how it shines at night. There is so much to see on both sides of the bus since the architecture of Chicago is interesting

Experience the stunning skyscrapers of Windy City that light up at night. Take a panoramic nighttime tour from the Magnificent Mile to Michigan Avenue past the Chicago Theater and Buckingham Fountain.

Chicago History, Culture, and Architecture Walking Tour

Check rates at Chicago History, Culture, and Architecture Walking Tour

This is a great way to hear about Chicago's history and architecture. Take a private stroll or share walks with family or friends for this architecture tour. You can see old and new architecture, try delicious local treats, see beautiful boats tour the river. 

Chicago Architecture Center Exhibit Admission

Check rates at Chicago Architecture Center Exhibit

The Chicago Architecture Center or CAC is located at the south end of Magnificent Rock near Michigan Walker Intersection. You'll discover super-sized models of architecture from around the world.

The vouchers give you access to two floors of imaginative exhibitions at the city's newest cultural venue.

Chicago Art Deco Skyscrapers Walking Tour

Check rates at Chicago Art Deco Skyscrapers Walking

The luxurious materials and geometric decorations of Art Deco represent the opulence and optimism of the decadent 20s. Visit some of the city's most beautiful architecture and learn about the history and characteristics of this modern decorative style.

Final Thoughts on the Best Chicago Architecture Tours

These are the best ways to tour Chicago architecture and see all the unmissable attractions. I've taken every single one of these tours, including ones not mentioned and found them worth the money.

I enjoyed seeing the towering skyscrapers and iconic landmarks. The tours offer a fascinating glimpse into the architectural history of the Chicago. Not to mention, it's nice to play tourist in my own back yard.

As a visitor, be sure to plan your tour in advance and consider factors such as weather and time of day to make the most of your experience. Don't forget your camera to capture the stunning views along the way.

Whether you're an architecture enthusiast or simply looking to appreciate the city's remarkable skyline, a Chicago architecture tour is a must-do activity. The buildings are inspiring structures and some are a marvel of innovative designs that have shaped this iconic city.

Whether you go on water, in the air, or on foot , book your tour today and embark on a journey through Chicago's architectural wonders.