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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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Downtown Chicago architecture itinerary

.Chicago is full of truly unique architectural wonders. The birthplace of the world’s first skyscraper, the city’s downtown has always been a place for architectural innovations. Today, it’s home to some of the most striking and recognizable structures in the world. If you’re looking to explore Chicago’s downtown architecture, you’re in for a packed day of breathtaking buildings and one-of-a-kind gems in the Loop, River North, and beyond.

Architecture in the Loop

Rookery Building On the National Register of Historic Places and a Chicago Landmark, the picturesque Rookery was designed by famed architectural partners Burnham and Root. Built during a transition period in architectural construction, it uses both load-bearing masonry and steel frame elements of the Chicago School of Architecture. Frank Lloyd Wright redesigned the two-story skylight lobby in 1905 – 1907. 209 S. LaSalle St.

Willis Tower An architectural achievement , the skyscraper designed by the renowned firm Skidmore, Owings & Merrill rises to a height to 1,450 feet. See breathtaking, 360-degree views of Chicago from one of the Western Hemisphere’s tallest buildings on its observatory Skydeck Chicago and experience The Ledge . 233 S. Wacker Dr.

Aqua Tower Located near the shores of Lake Michigan, this water-inspired tower is no standard skyscraper — it’s more like outdoor sculpture. This shimmering multi-use high rise by “genius grant” MacArthur Fellowship winner Jeanne Gang connects strongly to the outdoors and the city, with outdoor terraces that give it its distinctive undulating appearance. 225 N. Columbus Dr.

Pritzker Pavilion Located in the heart of Millennium Park , Pritzker Pavilion is a show-stopping venue for music, dance, film, and more. The dynamic stainless steel bandshell, designed by legendary architect Frank Gehry, captures the feeling of movement and energy. The trellis system overhead provides precisely placed speakers for a perfect acoustic experience. Set against the skyline, it’s an unforgettable place to see a show. 201 E. Randolph St.

Monadnock Block The last of the great masonry skyscrapers, the Monadnock ‘s solid block form conveys strength and sturdiness, though it is actually comprised of two narrow, connected office towers. Its architects Burnham & Root insisted on vertical simplicity and it is famed for its absence of ornamentation. The south addition is an early example of steel-frame construction. A harmonious combination, they mark the end of one architectural tradition and the transition into a new one. 53 W. Jackson Blvd.

Architecture near The Magnificent Mile

875 N. Michigan Ave. (formerly the John Hancock Center) One of the most iconic buildings of the city’s skyline, 875 N. Michigan Ave. — with its gutsy design in the tradition of industrial Chicago — offers a stunning view 1,000 feet up from the award-winning 360 CHICAGO (formerly the John Hancock Observatory). Additionally, The Signature Room at the 95th and The Signature Lounge at the 96th both offer terrific views of the city while you enjoy food and drinks. 875 N. Michigan Ave.

Wrigley Building For over 75 years, the Wrigley Building has been recognized as one of Chicago’s most attractive buildings. Its dazzling white terra-cotta cladding, striking architecture, and nighttime lighting have established it as a symbol of Chicago in many books, films, and television programs. This splendid building is an unforgettable site, day or night. 400 N. Michigan Ave.

Historic Water Tower This diminutive limestone tower stands proud in a cityscape of sleek glass and steel architecture. As one of the few buildings to survive 1871 Great Chicago Fire, it is a beloved symbol of Chicago’s enduring spirit. Resembling a miniature medieval castle, the Gothic-style structure was built in 1869 by William W. Boyington and is part of the Old Chicago Water Tower District, which includes the Chicago Avenue Pumping Station and a Fire Station built in 1904. 806 N. Michigan Ave.

Tribune Tower A Chicago Tribune competition in 1922 spurred a flood of international entries all vying to create “the most beautiful and distinctive office building in the world” for the newspaper’s new headquarters. The design by the New York firm Howells and Hood was selected out of over 250 concepts and today their Neo-Gothic limestone tower — complete with elegant buttresses, beautifully carved stonework, and an octagonal campanile — forms a grand gateway to The Magnificent Mile. 435 N. Michigan Ave.

Architecture in River North

Marina City Designed by the great Chicago architect Bertrand Goldberg, these riverside twin “corn cobs” fascinated Chicago and the world when it opened in 1962. At that time, the mixed-used complex was the tallest residential building and tallest concrete structure in the world. 300 N. State St.

Trump Tower Chicago The 92-story condo/hotel tower is Chicago’s second-tallest building, with a height of 1,398 feet including its needle-like spire, and was designed by acclaimed firm Skidmore, Owings & Merrill (who also brought Chicago the Inland Steel Building, Willis Tower, and the 875 N. Michigan Ave.). The gleaming glass, steel, and concrete structure rises prominently from its base at an oblique angle along the Chicago River’s curve, though a series of three setbacks that are level with the height of its surrounding neighbors and provide visual context within the skyline. 401 N. Wabash Ave.

330 N. Wabash (aka IBM Plaza and AMA Plaza) Developed by a master of the modernist movement, Ludwig Mies van der Rohe, this straightforward, rectangular monolith was the last American office building he designed. Steel and glass combine in shades of black and gray to form an archetypal example of the “Miesian” skyscraper and his aesthetic: minimalist, exact, symmetrical, functional…an ethos famously summed down to “less is more.” 330 N. Wabash

theMART Encompassing 4.2 million square feet, theMART is the world’s largest commercial building, largest wholesale design center, and one of Chicago’s premier international business locations. The massive space hosts many trade shows and events, and public areas include high-end kitchen and bath showrooms and retail shops. And in the evenings from March through December, the landmark building’s facade lights up with Art on theMART . 222 N. Merchandise Mart Plaza

Architecture boat tours

One of the best ways to learn more about the downtown cityscape is through an architecture cruise along the Chicago River. One of the most popular options is the Chicago Architecture Center River Cruise aboard Chicago’s First Lady , which covers the stories behind more than 50 buildings and structures along the waterway.

Other skyline tours by boat are held aboard   Shoreline Sightseeing , City Cruises , Chicago Fireboat Tours , and Wendella Sightseeing Boats . All offer great views and great stories of Chicago’s iconic skyscrapers.

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• Architecture River Tour

Windy City wow

World-famous landmarks.

There’s nothing quite like seeing Chicago’s world-famous architecture from all three branches of the Chicago River. From hidden treasures to the city’s most well-known sights, you’ll view over 40 Chicago landmarks on our 75-minute Architecture River Boat Tours. 

Enjoy the spectacular views as you listen to our tour guides tell you how Chicago’s buildings, architecture, and engineering made the city famous.

Casting off

Our Architecture River Tours depart from two docks, one at Michigan Avenue and the other at Navy Pier. No matter which dock you depart from, you’ll see all of the spectacular sights as you tour the Chicago River.

Michigan Avenue

401 N. Michigan Ave

Steps off of Chicago’s Magnificent Mile, our Michigan Avenue dock starts your tour in the heart of the Chicago River.

124 N. Streeter Drive

Start your tour down the Chicago River at our Navy Pier dock, which sits at the entrance to the iconic Navy Pier boardwalk. This dock is more accessible to wheelchairs.

Our Architecture River Tour takes you up and down the three branches of the Chicago River, providing breathtaking views of Chicago’s famous skyscrapers and landmarks at every turn.

Adults: $49.95

Children (3-12): $26.95

Children 2 and under: Free

Tour highlights:

• 75-minute, guided boat tour
• Unique views from the water create an entirely new perspective of the city
• 40+ landmarks including the Tribune Tower, the Wrigley Building, and Marina City
• Hear the stories of Chicago’s architects and engineers while viewing their magnificent buildings

Sightseeing in Chicago?

Chicago CityPASS® tickets save 48% on premier admission  to Chicago’s top 5 attractions, including the Architecture River Tour. Visit the attractions at your own pace, in any order, over a 9-day period. One easy purchase and mobile ticket delivery saves you time and money.

Book an Architecture River Tour

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Now in its 83rd season, Shoreline Sightseeing operates Chicago's largest and most diverse fleet of cruise boats and water taxis with 11 major tour vessels and 7 water taxis.

(312) 222-9328 ext. 1 [email protected]

• Skyline Tour
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Frank Lloyd Wright in Oak Park

Oak Park is home to the world’s largest collection of buildings designed by Frank Lloyd Wright. View the exteriors of nearly a dozen of Wright’s structures.

Premier tour*

This one-hour walking tour covers nearly a dozen homes on Chicago and Forest avenues and on Elizabeth Court.

Special thanks to the Frank Lloyd Wright Trust for their valuable partnership over the years. Visit www.flwright.org to view interior tours offered by the Trust to complement your CAC “Frank Lloyd Wright in Oak Park” tour.

• 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.
• Ticket price includes entrance to the Chicago Architecture Center within 7 days of your tour. View the CAC's hours .

*Premier tours are free for Deco members and above. Learn about our membership levels .

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Upcoming Frank Lloyd Wright in Oak Park Tours

Sunday apr 28.

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Chicago Walking Tours

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Embark on an unforgettable journey through the Windy City with Free Chicago Walking Tours. Our guided explorations take you through the vibrant tapestry of Chicago's most iconic neighborhoods and landmarks, unveiling the stories and spectacles that make the city truly unique.

Our meticulously curated tours, lasting approximately 2-hours, cover a distance of just over a mile, ensuring a comfortable pace for all. Spearheaded by seasoned Chicago tour guides, each walk is a blend of entertainment, education, and exploration. Check out our comprehensive TOUR CALENDAR to find and book your next adventure, or delve into the details of each tour by clicking on the images below!

For larger groups of more than 6, or to book a private, personalized tour, navigate to our PRIVATE TOUR page and complete the contact form. Our private tours offer an intimate, tailored experience, making them perfect for family outings, educational trips, or corporate team-building exercises. With rates starting at a mere $250 for a 2-hour guided tour accommodating up to 20 individuals, Free Chicago Walking Tours offers the most competitive private tour rates in the city.

Discover Chicago from a new perspective, witness its architectural marvels, historical landmarks, and cultural hubs, all while enjoying a leisurely walk. Whether it’s the bustling Magnificent Mile, the historical charm of the Wrigley Building, or the serene beauty of Millennium Park, each tour is a window into the soul of Chicago.

Free Chicago Walking Tours is not just a tour service, it’s your gateway to experiencing Chicago like never before. Reserve your spot today and step into Chicago’s rich tapestry of history, architecture, and culture. Your captivating journey through the heart of Chicago awaits!

Our Walking Tours

Chicago Holiday Tree & Lights Tour

Participants will embark on a festive journey through city streets adorned with twinkling lights, majestic trees, and exquisite window displays, accompanied by stories of Chicago's rich holiday traditions and historical seasonal narratives. The tour's highlight includes a visit to the "perfect" Christmas tree at Millennium Park, alongside several other picturesque spots.

The adventure begins just outside Bloomingdale's on the 2nd floor of 900 N. Michigan Ave Shops, home to a stunning indoor 50ft Christmas tree. The route meanders down the iconic Magnificent Mile, famed for its holiday-ready shops, offering numerous indoor stops for guests to warm up.

Chicago Pedway Winter Tour

Embark on a cozy adventure with the Chicago Pedway Tour, unveiling the “city below the city” stretching from the State of Illinois Building to the Cultural Center. This warm, indoor expedition uncovers the Pedway's history, linking over 50 buildings across 40 Downtown Chicago blocks. Marvel at renowned architecture, art, and impressive office lobbies as you traverse this subterranean network.

The Pedway Tour offers a unique glimpse into Chicago's heart, all while staying comfortable indoors. As you meander through its interconnected pathways, the Pedway unveils a blend of the city's historical richness and modern allure. Experience the Windy City from a vantage point like no other, and discover the stories etched beneath its bustling streets.

Chicago Loop Interior Tour

Dive into Chicago's architectural marvels, birthplace of the skyscraper, and home to legendary design maestros shaping the Chicago style. Millions flock here to bask in its architectural heritage, yet many overlook the rich interiors of these historic and modern structures. Our tour remedies this, guiding you through buildings whose interiors narrate the city's history, culture, and artistry.

While the skyline captivates, the inner beauty of Chicago's buildings is equally enchanting. With years of delivering insightful architecture tours, we unveil the mesmerizing interiors often missed. Our guests are continually awestruck by the elegance within, and we're confident you'll share this sentiment, discovering a new dimension of Chicago's architectural narrative.

Chicago Crime & Gangster Tour

Join us on a thrilling exploration of Chicago’s notorious past with Free Chicago Walking Tours’ Chicago Crime & Gangster Tour. Journey through the rise of the Chicago Mafia, and uncover hidden and famed Mob haunts in the scenic locales of River North and the Loop.

Wind your way through the River North area learning about the multiple gangs and their leaders that were vying for a piece of the prohibition pie. Stops at Marina City Towers and the Lasalle Street Bridge will help explain how all of these characters crossed paths and shaped the future of Chicago.

Chicago Off the Grid Tour

Forget stuffy museums or the standard architecture strolls and get lost in the beauty of Chicago's urban jungle on the new Off the Grid Tour. Hosted by ACME Hotel Company and Free Chicago Walking Tours, the immersive walking tour showcases some of the city's most Instagrammable spots including Death Alley and the Tiffany Glass Dome at the Chicago Cultural Center, among others.

Chicago Riverwalk & North Loop Tour

A blend of history, architecture, and scenic splendors with our Riverwalk & North Loop Walking Tour, offering a diverse taste of Chicago’s essence. Commencing at Du Sable Bridge, the seed of Chicago’s rich history dating back to the 1670s, we amble along the Chicago River, pausing at iconic sites like Trump International Hotel & Tower, Marina City Towers, and the Heald Square Monument, each narrating unique chapters of Chicago's tale. The Eastland Disaster tale by the river shores adds a historic poignancy to our expedition.

The tour unfolds Chicago’s artistic flair at Monument with a Standing Beast and the famed Picasso, culminating at the Chicago Cultural Center. Here, the world’s largest Tiffany Glass-domed roof awaits, marking a grand finale to a tour drenched in Chicago's multifaceted narrative, an experience not to be missed.

Chicago Total Loop Tour

Immerse in the cradle of American “downtown” in our Chicago Total Loop Walking Tour, encompassing the architectural grandeur, retail history, and the iconic Chicago River. We start at The Sears Tower and learn about "the architectural equivalent of the moon landing", the innovative design and construction of what would be the tallest building in the world for 25 years.

This unique two-hour, two-mile journey weaves through the heart of Chicago, unveiling the rich history, vibrant public art, and characters that form the essence of the city. From the grandeur of Millennium Park to the stunning display of Chicago's Picasso, we'll explore stories etched in stone and time.

Chicago Gold Coast Neighborhood Walking Tour

Chicago's Gold Coast is one of the city's most iconic neighborhoods. With the shores of Lake Michigan on the east, this is one of the most expensive zip codes in all of Illinois. Nestled among these quiet, tree-lined streets you'll find elegant multi-million dollar brownstones, numerous historic mansions and some of the wealthiest families in Chicago.

But this area wasn't always so wealthy. Once upon a time, this was marshland used as burial grounds. The area began to change in 1882 after Potter Palmer, one of Chicago’s business legends, built a castle-like mansion on Lake Shore Drive. Thereafter, Chicago’s wealthy citizens transformed this area into the city’s most exclusive residential enclave.

Chicago Loop & Public Art Walking Tour

Chicago is home to more than 500+ pieces of public art in more than 150 municipal facilities across the city. Chicago’s Loop is home to some of the most fascinating and picturesque pieces in the collection including sculptures by Picasso, controversial pieces such Monument with Standing Beast and learn how Chicago was invaded by decorative life size cows in 1999!

Throughout the tour you’ll be introduced to the artists responsible for the pieces, how the city reacted to their unveiling and get up close and personal with Chicago’s most prized possessions.

Chicago Millennium Park & Michigan Avenue Walking Tour

You will get to see so much of what makes Chicago so special on this tour. The Magnificent Mile, The Chicago River, Millennium Park, Buckingham Fountain and more! Your meeting spot is outside the entrance to on of Chicago's most beautiful buildings - The Wrigley Building.

From there the group will head south down Michigan Ave learning about some of the folks that helped put Chicago on the map hundreds of years ago. You'll have incredible photo opportunities of the Chicago River as you make your way to Chicago's famous Millennium Park.

About Free Chicago Walking Tours

With a variety of engaging tours lasting around 2-hours, we offer a comfortable pace to explore just over a mile of Chicago's most captivating neighborhoods. Our experienced Chicago tour guides lead you on a journey of discovery, sharing intriguing stories and fun facts that bring each locale to life.

Our diverse tour offerings are designed to cater to a wide range of interests. Whether you’re enchanted by the holiday lights, intrigued by the historical narrative, or keen on architectural wonders, we have a tour tailored just for you.

Free Chicago Walking Tours are built by Our Local Chicago Guides who all share a passion for the city we call home. Each guide has carefully constructed their tours to ensure the perfect mix of their personalities, Chicago's history & Chicago's architecture.

If you're new to Chicago be sure to read our Chicago Blog for tips and tricks on how to make your stay more pleasant including Your Guide to Getting Around Chicago  & Top 20 Free Things to do in Chicago .

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Chicago’s Secret Interior Architectural Walking Tour

Discover the hidden interiors of Chicago on this Exclusive Secret Interior Architectural Tour. See the most iconic buildings on a guided walking architecture tour. Learn about the architectural innovations that make each building unique.

Embark on a journey with seasoned guides to uncover the exquisite domes, shimmering mosaics, and elaborate craftsmanship hidden inside Chicago’s architectural marvels. Meander through the legendary buildings of Chicago’s Loop, and immerse yourself in the narratives of ambition, intrigue, and fame. Witness firsthand the ingenious methods architects and engineers utilized to address the challenges of illumination and structural integrity, all in their quest to leave an indelible mark on the world’s architectural stage. 

Delve deeper into the architectural innovations and styles that make each building unique, from the pioneering skyscrapers that defined a new era of cityscapes to the modernist masterpieces that reflect Chicago’s ongoing architectural evolution. Discover hidden architectural features, the significance of various design elements, and how Chicago’s architecture has influenced global building trends. Join for an unparalleled exploration of Chicago’s architectural splendor, both inside and out. This tour is not just a walk through the city’s physical history, but a step into the stories that shaped Chicago into the architectural icon it is today.

Tours run daily at 11am and 1:00pm for approximately 2 hours.

Adults $29 Seniors $27 Youths $22 Kids under 6 go free!

Tour Itinerary 

• Chicago Loop
• LaSalle st. Financial District
• Chicago Union Station
• Rookery Building (closed on Sundays)
• Chicago Board of Trade or Field Building
• Marquette Building
• Palmer House
• Monadnock Building or Chicago Cultural Center
• Marshall Field and Company Building (end location) (Itineraries are subject to change)

Are you ready to learn more about Chicago’s architecture? Be sure to bring your camera – you’re not going to want to miss these shots. Book Chicago’s Secret Interior Architectural Tour today!

BOOK YOUR TOUR NOW

By Phone: (708) 488-6343

Tour departure location.

Union Station, 225 S Canal St, Chicago, IL 60606, USA

Please meet your tour guide inside the Great Hall under the Clinton Street Sign!

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Fun Free Things To Add To Your Chicago Bucket List

A s a Chicagoan, it's a lot of fun to recommend incredible ways to experience this city  -- bonus points if those excursions are free. While Chicago can be expensive, just as any city can, it's also blessed with a ton of fantastic ways to spend a day without spending a dime (on admission, anyway). Not all of these activities will last an entire day, but a few of them are in the same area of the city, making for an easy way to hodgepodge together a day of adventure.

There are dozens of things to do for free around Chicago. Sometimes free neighborhood festivals or performances add to that list. Even so, some free activities like the ones below are the best no matter what time of year it is. While everyone has their opinions on Chicago attractions, this list is informed by this writer's personal experiences in the city. So please, visit the incredible Windy City and do more than touch the grimy Cloud Gate sculpture.

Read more: 12 Most Underrated Travel Destinations Around The World

Walk The Lakefront Trail

You may or may not know that Chicago is part of the United States' third coast, a nickname derived from being nestled alongside Lake Michigan. Chicago is a neighbor to the largest freshwater lake in the country, and we're incredibly proud of our gorgeous lake. There is no better way to appreciate its vastness as well as the city skyline than from the sprawling Lakefront Trail.

The 18.5-mile trail follows the coastline of the city with over 50 connecting points so you don't have to traverse the whole thing. There are also some picnic tables and benches strewn along the trail to offer resting points. It is stroller-friendly if you have little kiddos along. Folks also love to rollerblade as well as bike down the path. Just watch out for the odd pedicab operator -- it's not worth the fees.

Walking the Lakefront allows you some time to disconnect from the bustle of the city and enjoy the calming rhythms of the water. You can watch the boats bobble by and even catch the fireworks off of Navy Pier if it's the summertime.

Visit The Chicago Cultural Center

A breathtaking piece of architecture downtown, the Chicago Cultural Center (the CCC) is a hidden gem. That's an overused term, but truly, the CCC fits the bill. It even houses the largest Tiffany stained-glass dome on earth, which is well worth a short visit to see on its own.

Given that it's across the street from The Bean area of Millennium Park, it's almost silly not to stop by. Spending more than just a few minutes admiring the architecture might not be best for families with little kids. Although The Learning Lab is an interactive studio setting with activities for all ages, the experiences here vary.

Adults or artsy kids will appreciate the rotating cultural and art exhibitions on top of tours of the CCC to witness all of the architectural touchpoints. Some of the past exhibits have included Giving Back: The Soul of Philanthropy Reframed and Exhibited, The Great Chicago Fire in Focus, and Stand Up for Landmarks! Protests, Posters & Pictures.

Spend A Day At The Lincoln Park Zoo

As one of the oldest zoos in North America, Lincoln Park Zoo (LPZ) has been part of Chicago's history since 1868. This wonderful zoo resides in the hip Lincoln Park neighborhood, and its hundreds of acres of nature, animals, and gardens will help you walk on the wild side. LPZ houses over 1100 animals from across 200 species. It was even the first place to support the birth of an American bison in captivity to help bring the species back from the brink of extinction.

With 15 exhibit areas on top of eateries and the garden, it's easy to spend a whole day at LPZ. It's designed in a sort of loop so you can meander your way through the zoo with breaks built in as needed. This is one of the best things to do with kids since the animals, zookeeper chats, and snacks are enough to keep those little faces smiling. Plus who could say no to the beautiful Endangered Species Carousel?

Wander The Chicago Riverwalk

Although Lake Michigan is Chicago's shining star of a waterway, we also deeply love our Chicago River. This marvel of human engineering is always a hotspot for people watching or meandering. Plus, from March through December, you can experience the free Art at THE MART projection show on the side of Merchandise Mart. This video art installation is a calming way to spend an evening with plenty of seating space for everyone.

Alongside the river is a free Riverwalk with sidewalk cafes, public art, and seating areas for you to enjoy all the views downtown has to offer. That includes the dozens of architecture tour boats that scoot along the river every day -- don't forget to wave at the passengers! Contrary to public belief, Chicagoans are pretty nice.

An evening on the Riverwalk is a wonderful date night idea. Grab a drink at one of the eateries along the river, visit the McCormick Bridgehouse & Chicago River Museum, or just find some live outdoor music. All of that and more is available along the Chicago Riverwalk.

Explore Millennium Park

Home of Cloudgate, aka The Bean, Millennium Park is much more than just residency for a shiny bean-shaped sculpture. There are fountains, a seasonal skating rink, a music performance venue, and so much more. With a range of things to do and see, this is a great activity for families or any kind of traveler. Millennium Park has become one of the quintessential tourist attractions in Chicago, with The Bean being its most iconic visual.

Believe it or not, Millennium Park is actually part of an even bigger park. It covers nearly 25 acres of Grant Park. During the warmer months, there are myriad musical performances in the Jay Pritzker Pavilion which are free of charge. The biweekly Summer Music Series showcases a range of musical genres and the free film series are two of the most popular free events at the pavilion.

If you want more natural experiences in the park, go find some solace in The Lurie Garden. On the south side of Millennium Park, this garden area encompasses some beautiful flora, demonstrating the fascinating duality of Chicago. The dark area houses the plants who prefer shade as a metaphor for the city's past while the light area with sun flourishing plant life represents the city's bright future.

Revel In The Greenery At Garfield Park Conservatory

Over in Garfield Park, the free Garfield Park Conservatory has been showing Chicagoans and visitors alike the beauty of nature for over a century. This botanical garden is always a fan-favorite way to spend an afternoon. You'll find refuge there, particularly on brutally cold winter days.

Kids will marvel at the sheer size of the conservatory. It's home to one of the largest greenhouses in the country, soaring overhead with its massive windows. You're engulfed in sunlight even in the dead of winter. The conservatory's collection is immense including a few cycads, or palms, that are over 200 years old.

There are eight distinct garden areas at the conservatory including the Children's Garden, the Fern Room, and the Desert House. Our favorite part of the conservatory though, hands down, is the Palm House. As the name implies, this is where the conservatory houses its astounding palm collection. It's the largest room here and immediately transports you to a tropical paradise without leaving Chicago.

Get Artsy At The Intuit: The Center For Intuitive And Outsider Art

Since 1991, Intuit: The Center for Intuitive and Outsider Art has been offering art exhibitions aimed at everyone, not just traditional art museum types. The center's permanent collection includes around 1,100 pieces. Probably a better stop for couples, solo travelers, or groups of adults than families, Intuit is one of the foremost museums of both outsider and self-taught artists.

Some of the artists in Intuit's permanent collection include Miles Carpenter, Minnie Evans, Michel Nedjar, and Wesley Willis, just to name a few. Of course, one of the things that draws repeat visitors to the museum is the host of temporary exhibitions, introducing visitors to new artists.

But the star of the museum is the Henry Darger Room Collection. Darger was one of the city's most famous outsider artists who lived in a single-room apartment for almost four decades in Lincoln Park. This exhibit at Intuit recreates Darger's one-room world.

Embrace History At Jane Addams Hull-House Museum

Founded by Jane Addams, the first woman to win a Nobel Peace Prize, this free museum focuses on policy and underserved communities. Technically the museum is free, however, there is a $5 suggested donation if you feel so compelled.

Addams and Ellen Gates Starr co-founded the Hull House in 1889 to serve European immigrants. It was one of the first social settlements (or neighborhood welfare agencies) in North America. The museum is located within two of those original settlement buildings -- the Hull Home itself and the Residents' Dining Hall.

With the museum's collection of over 5500 artifacts, visitors get more insight into life on the Near West Side in the early 1900s. Most importantly, it showcases how immigrants fit into the fabric of the country's biggest and most diverse cities. Visiting exhibitions shed more light on social dynamics, too. A couple of their past exhibitions have included True Peace: the Presence of Justice and The Best Side: The Art and Soul of Jackie Hetherington.

Frolic In The Flowers At The Lincoln Park Conservatory

Visiting the Lincoln Park Conservatory is a perfect way to spend a free day in Chicago, especially with the Lincoln Park Zoo. The two are right next to each other, and this conservatory is much smaller than the Garfield Park Conservatory. Unlike the facility at Garfield Park, the Lincoln Park Conservatory only houses four display rooms.

Despite that petite size, these rooms hold some incredibly rare plants. The Orchid Room is the most incredible spot with some unusual flowers you're unlikely to see anywhere else. Plus, the Formal Garden is one of the oldest public gardens in the city dating back to the 1870s.

Visiting the conservatory is free for self-guided tours. However, if you want a guide from the facility, you can pay a small donation. The Lincoln Park Conservatory is open every day. Since they're indoors, the four plant houses are open all year round, although the outdoor gardens have seasonal limits. Your best bet to see the gardens at their best is to visit them in spring and summer as the city's nature comes back to life. Keep in mind that there can still be snow and chilly temperatures in Chicago as late as April.

Take A Shot At The Museum Of Contemporary Photography

Located at Columbia College, the Museum of Contemporary Photography (MoCP) is one of the only museums of its kind in the region. Dedicated wholly to photography, the museum demonstrates how photographs represent life in a brief, still moment. The museum was founded in 1976 in place of the former Chicago Center for Contemporary Photography. It houses a collection of 17,000 works from over 1,800 artists.

Like several of the other free activities we've listed so far, the MoCP is also open every day except for major holidays. It's always free to visit and docent tours for groups of 10 or more through the museum are also free.

In addition, MoCP has some incredible temporary exhibits, showcasing how much can still be done in the realm of photography. A few of their past shows included Refracting Histories, American Epidemic: Guns in the United States, and Chicago Stories: Carlos Javier Ortiz and David Schalliol.

Get In Some Culture At The National Puerto Rican Museum

Providing art exhibitions, hands-on workshops, films, and even a fine arts/crafts festival, the National Puerto Rican Museum is a great stop on your Chicago tour. Formerly known as the National Museum of Puerto Rican Arts & Culture, it is an important part of Chicago's cultural lexicon, housed in the historic Humboldt Park Stables and Receptory, a charming Queen Anne brick building.

Its name was officially changed to the National Puerto Rican Museum, as it is the only museum of its kind in the country. The only museum wholly dedicated to Puerto Rican art and culture, it has a lot to say about the island's culture.

This museum does have more limited availability than other locations we've mentioned thus far. It is only open Tuesday through Saturday each week. Docent-led tours are available for groups of 10 or more with a small fee attached and must be scheduled at least a week ahead of your visit.

Enjoy More Art At The National Museum Of Mexican Art

The most significant museum of Mexican art and culture in the country, the National Museum of Mexican Art (NMMA) is a one-of-a-kind experience. Housed in the largely Mexican-American neighborhood of Pilsen, the museum is the perfect segue to experience all the free public art in the neighborhood itself. Its collection includes over 18,000 pieces dating back to ancient Mexico.

Among the most important works in the museum's collection are Máscara con figuras pre-Cuauhtémoc by Alfonso Castillo Orta, The Legacy of Manifest Destiny by Marcos Raya, and Homage to Posada by Carlos Cortéz. The museum is open Tuesdays through Sundays as well as on major holidays. It is also incredibly accessible for anyone with additional sensory needs. The NMMA app is sensory-friendly, while the museum has free bags with items like earplugs and sunglasses available to check out during your visit.

Because of the size of this museum, you'll want at least a few hours to enjoy it to its fullest. It's a terrific excuse to get out and enjoy all the delectable food Pilsen has to offer.

Play Around At Navy Pier

It surprises visitors that Navy Pier itself is a free activity. You don't have to pay to enjoy the pier, its sights, or its vibes. What you'll pay for here is anything else you want to add to your day of fun, whether that means tickets to the Chicago Shakespeare Theatre, the Chicago Children's Museum, carnival rides, or any other attractions during your visit. Year after year, Navy Pier is one of the most visited attractions in the Midwest.

There is a wide range of dining options here, too, from the charming Lirica to a classic deep dish at Giordano's, making this a perfect family stop. Kiddos have a ton to keep them entertained, with rides as well as food options to keep them going. Because of this, Navy Pier is one of the most family-friendly locations in Chicago. Plus, most of it is indoors (except the carnival rides) so it's ideal all year long, even if the weather isn't cooperating.

See A New Side Of The City From The 606

A much different visual experience than the Lakefront Trail, The 606 is a 2.7-mile elevated trail that takes you through multiple Chicago neighborhoods. You can see in real-time the differences between these communities from the garden-like walking, biking, and jogging route. It is open every day, connecting Wicker Park, Bucktown, Logan Square, and Humboldt Park.

As it's primarily a pedestrian trail, you'll see lots of walkers, runners, and even roller skaters. Bikes are also welcome on the trail with rental stations dotted throughout the trailway. There are also public art installations throughout The 606 for everyone to enjoy. Like the Lakefront Trail, The 606 is a wonderful way to appreciate the greenery of the city while also experiencing several of its neighborhoods in one fell swoop.

This is one of those activities that frequent Chicago visitors may appreciate most. Once you've visited several times and gotten to know Downtown and the heavily touristed areas, you may be more open to exploring the lesser-known sights.

Why We Chose These

There are a lot of stereotypes about Chicagoans. While we are known for being a little gruff at times, we're also extremely rooted in Midwestern niceness. Because of that, we love to talk to everyone about our favorite city. The free activities listed here are among this writer's favorite things to do around the Windy City.

A lot of visitors will make a beeline for The Bean and may not know the other iconic parts of the city. We highly encourage you to explore more of the sprawling Millennium Park and the city at large. It doesn't have to cost a fortune to get to know how incredible Chicago is.

When you live in a huge metropolitan area, things are quite expensive. As such, knowing what can be done for free on a weekend or time off is a big part of keeping the city life exciting. There are far more things one can do in Chicago free of charge, but these are the best ways to spend your time here. The array of activities gives you a broader understanding of the complexities of Chicago, including its natural beauty and cultural diversity.

Read the original article on Explore .

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Chicago Walking Tours

Consulte nuestro calendario a continuación para ver todos los recorridos, así como las cosas que hacer y los consejos de viaje.

Visitas destacadas.

Architecture Tour

Architecture tour destacados.

Haunted History

Haunted history destacados.

Loop and Millennium Park

Loop and millennium park destacados.

Riverwalk and History Tour

Riverwalk and history tour destacados.

Lincoln Park & Blues

Lincoln park & blues destacados.

Winter Riverwalk

Winter riverwalk destacados.

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.  

• Visitas a pie
• Architecture Tours
• Tour en Bus
• Tourist Discount Passes
• Chicago Travel Tips

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.

En Español:

• Tour del North Loop y Millennium Park
• El Tour Chicago Riverwalk
• Audio Tours

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...

• What is the Best Chicago Architecture Tour?
• 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

PRIVATE TOURS

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.

Find out more about private tours...

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