It doesn’t matter if you are a local or a first-time visitor, experiencing the city’s architecture on foot or from the water with a knowledgeable guide is a unique and enriching experience. From sleek glass skyscrapers to intricate Art Deco structures, and from street art to cultural landmarks in our neighborhoods, these tours stand out as some of the finest attractions in Chicago. Dive deep into the design, engineering, and construction stories behind the city’s most stunning buildings, all while enjoying guided walks, bus rides, and boat tours. Even for first-timers, these architecture tours also serve as comprehensive sightseeing adventures, offering the perfect opportunity for Instagram-worthy moments.
Get to know the architectural wonders of Chicago through these tours
This, is my list of amazing tours suitable for both tourists and Chicago residents.
Important: The prices given are for reference as they may change at any time and without prior notice. Please check the prices before booking your activities.
Chicago Architecture Foundation River Cruise
Gain a comprehensive view of Chicago’s skyline aboard Chicago’s First Lady. Marvel at over 50 architecturally significant buildings, from historic icons like the Wrigley Building to modern additions like the St. Regis. An expert guide will share insights into Chicago’s history, including the aftermath of the Great Fire of 1871 and pivotal moments in the city’s architectural evolution. Day and evening options available. $52
Shoreline Sightseeing Architecture River Tour
Embark on a 75-minute journey to witness more than 40 landmarks, including Tribune Tower and Marina City, with Shoreline Sightseeing. A knowledgeable guide unveils the stories behind the architects, engineers, and influencers that earned Chicago its “City of the Big Shoulders” moniker. $43-47
Chicago’s Original Architecture River Tour
Cruise the Chicago River in style, accompanied by a bartender and an entertaining guide. Explore the city’s architecture across all three main branches of the river, with a 45-minute option also available. $42
Short on time? Opt for the 90-minute “Greatest Hits” walking tour by the Chicago Architecture Foundation. Discover key landmarks such as the Chicago Theatre, Aqua Tower, Willis (Sears) Tower, the Wrigley Building, and the Art Institute of Chicago. $30
Explore Chicago’s ever-evolving architectural landscape with a 90-minute tour by the Chicago Architecture Foundation. Visit landmarks like 462 N. Park and the St. Regis, discussing their impact on the city’s changing environment and economy. $30
Frank Lloyd Wright Trust Bus Tours
Indulge in tours dedicated to the renowned architect Frank Lloyd Wright, including stops at the Rookery Building, Wright’s home, and studio in Oak Park, and the exquisite 1915 Emil Bach House. Lunch and a prosecco toast included. $195
Free Tours By Foot’s Architecture Tour
Experience an excellent overview of Chicago’s architecture on a budget with volunteer-led, pay-what-you-can two-hour walking tours. Visit landmarks like Cloud Gate, Marina City, and works by Frank Lloyd Wright, Louis Sullivan, and Mies van der Rohe.
Chicago Walking Tour: Art Deco Skyscrapers
Step back into the Roaring Twenties with a tour highlighting iconic Chicago buildings. Choose the Loop or Riverfront route to admire Art Deco constructions like One North LaSalle and the Carbide and Carbon building. $30
Chicago Mahogany Tours
Led by civic historian Shermann “Dilla” Thomas, these tours explore the history, contributions, and legacies of South Side neighborhoods, including architectural highlights from Bronzeville to Pullman.
Chicago For Chicagoans
Designed for locals by locals, these tours aim to build community and foster a deeper appreciation for Chicago’s neighborhoods. Enjoy walking tours and scavenger hunts in Albany Park, Chinatown, Pilsen, Beverly, and more.
Chicago Walking Tour: Modern Architecture
Delve into the city’s most famous modern buildings on this two-hour walking tour. Featuring designs by Ludwig Mies van der Rohe, the Harold Washington Library, and One South Dearborn. $30
White City Revisited
Explore the architectural impact of the 1893 World’s Columbian Exhibition on Chicago with a tour including visits to Jackson Park’s Garden of the Phoenix and Yoko Ono’s Skylanding sculpture. $30
Private Chicago Architecture Tour
Reserve a private tour for an exclusive exploration of the city’s impressive buildings, from Willis Tower to Gothic facades on the Magnificent Mile to Frank Lloyd Wright homes in Oak Park. Chauffeured transportation included. $930.60
Women in Chicago Architecture
Discover the contributions of female architects shaping Chicago’s skyline on this 45-minute virtual tour by the Chicago Architecture Foundation. $8 for the public, free for members
Brick of Chicago
Explore the significance of common brick in shaping Chicago. On this tour through neighborhoods like Logan Square, Hyde Park, and Bronzeville. Marvel at churches, greystones, and Gilded Age mansions. $12–19
Join a 2-hour neighborhood-centric tour by the Chicago Architecture Foundation, exploring historic Midway Park and showcasing works by local architects. Hear from Austin residents about revitalization efforts and the neighborhood’s history.
Uncover the cultural influence and art-architecture intersection in Pilsen on this two-hour tour by the Chicago Architecture Foundation. Visit residential, commercial, and cultural sites, exploring the rich history of the neighborhood. $30
Chicago’s architectural wonders stand as a testament to the city’s rich history, innovation, and resilience. Each building tells a story of Chicago’s evolution. Whether you’re a local seeking a fresh perspective or a visitor eager to explore the Windy City’s architectural legacy. These tours offer a gateway to a world where art, design, and history converge.
So, lace up your walking shoes, hop on a boat, or embark on a guided bus tour—discover the architectural tapestry that makes Chicago truly one of a kind.