Chicago Architectural Tour

Chicago Architectural Tour

World-Class Chicago Architecture: Chicago Buildings to See on Your City Tour

From the lakeshore to the banks of the Chicago River, from the North Side to the South Side, the city of Big Shoulders brims with some of the world's most spectacular architecture. Chicago's distinctive skyline is tenanted by world-class buildings like Willis Tower and the John Hancock building. Chicago buildings' history is rich, but the story of the city's skyscrapers is an ongoing tale as evidenced by new Chicago high-rise condos and cutting-edge contemporary Chicago skyscrapers. If you're planning to tour the city to get to know its architectural character or to reflect on an area for a potential real estate purchase, you will want to get to know the city from an architectural perspective. Take our "tour" and learn about what makes the Chicago skyline so unique and where you can find some of its most famous architecture.

About Chicago Buildings Tours

As a world-famous city, Chicago features many types of tours. From downtown walking tours to bus and boat tours, these tours showcase the greatest Chicago buildings to see. We've organized our content to reflect major areas of the city. Consequently, if you're visiting the East Side or the West Side of Chicago, you can easily scroll to the section to find a listing of the area's most celebrated buildings and architectural landmarks. As one of the largest cities in America, Chicago seems to have no shortage of captivating buildings, but we've tried to include the most renowned—the highlights that you absolutely do not want to miss on any tour of the city. If you are interested in Chicago architecture, enjoy our informative "tour" and learn what makes Chicago such a prominent American city in terms of architecture and style!

Many of the following architectural features are open to the public, but some are home to private residences. Even if you're only able to view them from their exteriors, they are well worth checking out owing to the significant contribution they make to the Chicago Skyline or Chicago history. Feel free to click on the links to learn more details about the buildings and structures that interest you most.

Downtown Chicago Architectural Marvels

Downtown Chicago Architectural Marvels

Downtown Chicago is loaded with many of the city's most notable architectural structures. As the commercial heart of the city, Downtown is very much the city's heart. Named the Loop because it has been encircled by rail lines, the downtown area of the city is enjoyably walkable if you choose to visit its famed structures on foot. Of course, public transportation and taxis are reliable too. The following structures are must-see attractions that you'll find in the Loop.

As one of the world's most notable architectural wonders, Willis Tower does truly deserve a visit on your Chicago building tour. Originally called the Sears Tower, Willis Tower was once the tallest skyscraper in the world. In fact, it held on to this title from 1973 to 1998. It remains one of Chicago's most popular tourist attractions with its 110 stories and popular Skydeck with its visually astounding views of the city and lake.

If you're a shopping guru, you definitely want to head over to State Street to check out Macy's. However, its building formerly and quite famously housed Marshall Fields. The Marshall Field and Company State Street Building was constructed in 1892. The granite building takes up an entire city block. As a National Historic Landmark, the building features on many tours of historic Chicago. This massive building includes a mosaic vaulted ceiling designed by Louis Comfort Tiffany that is among its signature ornamentation.

Sullivan Center is another famed Chicago commercial building that once housed the Carson, Pirie, Scott, and Company Store. The building was completed in 1899 and has been used for retail purposes since that time. Its decorative ironwork façade is one of its signature features.

If you're making your way down Michigan Avenue, you'll want to view the renowned Art Institute of Chicago. It's hard to miss thanks to its stone lions that guard its entrance. This landmark is one of the country's oldest and largest art museums and is home to famous works like Renoir's Two Sisters and van Gogh's Bedroom in Arles. The building itself was constructed for the 1893 World's Columbian Exposition and is constructed in the Beaux Arts style.

The Richard J. Daley Center is located in the Loop between Dearborn and Clark Streets. The tallest flat-roofed building in the world, the Daley Center, as it's known, is a fixture on Chicago building tours and even made an appearance in the Batman film Dark Knight. The building was completed in 1965 and is ornamented by a famous Picasso sculpture, another famous landmark of the city.

The Chicago Cultural Center is located in a distinctive building that used to house the Chicago Library. Completed in 1897, this building boasts some illustrious features like its doric columns, intricate mosaics, and walls of Cararra marble. The Tiffany glass dome that crowns the Sidney R. Yates Gallery is particularly noteworthy. The center features many exhibits and has become one of the city's most popular cultural attractions.

The Field Building was constructed in 1934 and is listed as a Chicago Landmark. Featured in the Art Deco style, the building is an important architectural feature in this part of the Loop where it sits at 135 South LaSalle Street.

Once the tallest building in Chicago, the Pittsfield Building was constructed in 1927 and is, today, a celebrated Chicago Landmark. The building is located in the Jewelers Row District of the city and includes a beautiful five-story atrium in its interior with balconies and gleaming surfaces. Today, the building is home to jewelers, medical offices, and various commercial businesses.

The Blackstone Hotel has hosted many presidents during its tenure. It was constructed in 1909 and has undergone substantial renovations. Although many of the historic features of the hotel were lost during its renovation, there are still numerous well-preserved spaces like its barbershop. The hotel has shown up in several films including The Color of Money and The Untouchables.

Overlooking Lake Michigan, the celebrated Drake Hotel was constructed in 1920 and is one of the city's landmark hotels. During it tenure, this historic hotel has hosted such notable guests as Winston Churchill, Prince Charles and Princess Diana, Herbert Hoover, Judy Garland, Elizabeth Taylor, Marilyn Monroe, Joe DiMaggio, and many others. Various films like Risky Business, What Women Want, and My Best Friend's Wedding have included the hotel in scenes. The hotel has long been famous for its Afternoon Tea.

If you're a fan of modern architecture, you will want to visit the Inland Steel Building that was completed in 1957. Its brushed stainless steel features pay homage to its post-WWII era of architecture. The building has been a Chicago Landmark since 1998.

Built in 1886, the Rookery is the city's oldest still-standing high-rise. The building features a steel frame and 12 stories. Its lobby was redesigned in 1905 by architecture Frank Lloyd Wright. The building is listed on the National Register of Historic Places and, today, provides a home for various commercial companies.

A Neo-Gothic skyscraper, the Tribune Tower is a distinctive part of Chicago's skyline. Located at 435 North Michigan Avenue, the building was completed in 1925 on the site of the former Tribune Tower that burned in the Chicago Fire. Currently, the building is being converted into high-rise condominiums and is supposed to be completed by 2020.

The Monadnock Building is an imposing building in the Loop that's located at 53 West Jackson Boulevard. The building was completed in 1893 and, at one time, was the world's largest office buildings. It is listed on the National Register of Historic Places and is regarded as one of the city's seminal skyscrapers.

Old Chicago Main Post Office

The Old Chicago Main Post Office is a sprawling nine-story building served as Chicago's main post office until the late 20th century when it was moved to a more modern facility. Today, the headquarters for Walgreen's occupies the building's 200,000 square feet.

Palmer House is an historic Loop hotel that was originally built in 1875 and was rebuilt in 1925. Today, the hotel is operated by Hilton but it continues to be revered for its historic features. Illustrious figures who have spent time at one of the illustrious hotel's incarnations have included Sarah Bernhardt, Eleonora Duse, Ulysses S. Grant, L. Frank Baum, Oscar Wilde, and Mark Twain.

Orchestra Hall was built in 1904 and features more than 2,500 seats. It is home to the Chicago Symphony Orchestra as well as other musical organizations. It is listed as a National Historic Landmark.

The Auditorium Building and its accompanying theatre date to 1889. Constructed by Louis Sullivan and Dankmar Adler, the building currently features home performances by the Joffrey Ballet. However, during it's tenure, it served as the home for the Chicago Symphony Orchestra and Chicago Civic Opera.

Chicago's Civic Opera House was completed in 1929. It is one of the largest auditoriums on the North American continent—second only to New York City's Metropolitan Opera House. The illustrious structure boasts a dazzling Art Deco design and is, today, home to the Lyric Opera of Chicago.

The historic Dearborn Station was constructed in 1883. While this brick structure no longer serves as a rail station, it does provide retail space and a shopping mall. Fans of railroad history will certainly want to view it.

Chicago River Highlights

The Chicago River is a major feature of the city. Many of Chicago's historic neighborhoods flank its banks. Today, some of Chicago's most notable structures can be viewed by taking a river tour or walking along the Riverwalk. Be sure to note the following on your Chicago buildings tour.

Famous for its Art Deco style, the Merchandise Mart is a massive structure located on a junction of two branches of the Chicago River. The building is a titan among Chicago buildings, owing to its 4,000,000 square feet. Until 2008, this building was so large that it warranted its own Chicago zip code! There are tours of the building, but it's certainly an impressive site even when viewed from river on a boat tour.

Marina City is situated on the north bank of the Chicago River and is a mixed-use building that is home to bother commercial and residential spaces. Marina City is noteworthy because of its "city within a city" complex. Completed in 1968, the structures that make up Marina City has a claim to fame of being the first urban high-rise residential complex in the country. As you view it, you're sure to note its distinctively mid-century modern style.

The dazzling Wrigley Building is one of the city's most recognizable buildings. Completed in 1924, the building was originally built to be the headquarters for the Wrigley Company. A picturesque feature on Chicago's Magnificent Mile, the Wrigley Building is located on the northern banks of the Chicago River. Modeled after the Cathedral of Seville, the building commands an arresting position on any Chicago River tour.

Michigan Avenue Bridge

Michigan Avenue Bridge

Spanning the Chicago River in downtown Chicago, the Michigan Avenue Bridge opened in 1920. Its decorative work, plaques, and sculptures underscore its eye-catching appeal and historic significance. The bridge was proposed as early as 1891 as a means to link parks on the city's North and South Sides. Most river tours and Loop tours will include this feature for a visit.

The building known as 330 N. Wabash boasts a commanding presence on the Chicago River. This building was constructed in 1973 and its one of the city's more modern skyscrapers. The building features 52 stories—several of which comprise the prestigious Langham Hotel, which has been called one of the best in the nation.

If you're a fan of contemporary architecture, don't miss checking out 150 North Riverside. This unique high-rise was completed in 2017. Because of its unique super-structure, the building only encompasses about 25% of its lot. It is situated on the west bank of the Chicago River and features 1.2 million square feet of office space.

If you're bound for the lake front, take time to check out the Chicago Harbor Light that's located at the mouth of the Chicago River and to the east of Navy Pier. The light was constructed for the 1893 World's Columbian Exposition. The light is active and does not allow for public access; however, you can still enjoy its distinctive exterior and position on the lakefront.

North Side Must-See Architectural Attractions

The North Side of Chicago features many historic neighborhoods and within them, you'll find some of Chicago's most historic and revered buildings. One of the city's most renowned architectural structures is Wrigley Field. This historic ball field opened in 1914. It is home to the Chicago Cubs and is the oldest ball park in the National Baseball League. For baseball fans, it's a must-see attraction on the North Side.

The John Hancock Center is a recognizable fixture of the Chicago skyline. Located at 875 North Michigan Avenue, this building was completed in 1969 and was constructed in the structural expressionism architectural style. When visiting this world-famous skyscraper, be sure to check out 360 Chicago, its celebrated observation deck located on the 94th floor of the building. It boasts dazzling views of the surrounding cityscape and lake.

Completed in 1921, the Chicago Theatre brims with Art Deco style. This structure is listed on the National Register of Historic Places and is also a Chicago landmark. Its marquee is a recognizable symbol of the city's cultural scene, but its interior is certainly worth touring or, better yet, witnessing along with a show or theatrical performance.

The Palmolive Building, also referred to as the Playboy Building, is located at 919 North Michigan Avenue. Completed in 1929, the building was built for Colgate-Palmolive-Peet Company but was purchased by Playboy Enterprises in 1965. Today, the building has been converted to residential condos.

Chicago Water Tower is located on the Magnificent Mile on your way northward from the Loop. Constructed in 1869, the tower is a major city landmark and was built to contain a large water pump. The distinctive castle-like architecture of this structure famously inspired the White Castle fast food chain.

The Bush Temple of Music was constructed in 1901 and once housed a piano company. It boasts French Renaissance Revival architecture. It has been listed as a Chicago Landmark since 2001.

The Uptown Theatre is currently closed, but recently, city residents have learned that funds have been set aside for its renovation. This Art Deco theatre was built in 1925 and features 4,381 seats. The largest theatre of its kind, the Uptown features a five-story lobby and is even said to rival Radio City Music Hall in terms of overall size. Residents of the city are certainly looking forward to its revival.

Located in Lincoln Park, the Biograph Theatre was built in 1914. Though it was housed a movie palace and was the site where John Dillinger was shot by FBI agents after viewing a film, the theatre, today, features live performances. This theatre is listed on the National Register of Historic Places and is also designated with Chicago Landmark status.

The Allerton Hotel is located on the Near North side heading north on Chicago's Magnificent Mile. The hotel, now known as the Warwick Allerton, is a Chicago Landmark and first opened its doors in 1924.

The Edgewater Beach Apartments was constructed in 1928 and is a co-op residential building that is famous for its pink façade. The building was recently added to the National Register of Historic Places and is regarded as a neighborhood jewel.

An important example of a 19th century urban school building, Assumption School was constructed in 1899 as a Catholic elementary school. It is built in the Beaux Arts style and features intricate brick and stonework. The school was famously founded by Mother Francis Xavier Cabrini in order to serve the community's Italian inhabitants. Upon opening, the school charged no tuition.

The Hotel St. Benedict Flats feature luxury "French-style" apartments. The building was constructed in 1882 and designed by architect James J. Egan. It is renowned for its stunning art glass windows and distinctive pressed metal features. In short, the building is simply too attractive to miss on your tour of the North Side.

West Side Architectural Attractions

As one of Chicago's major sections, the West Side contains many historic buildings that feature largely on Chicago history and architecture tours. The city is home to many historic churches, including Holy Trinity Orthodox Cathedral. This church is a Chicago landmark and also listed on the US National Register of Historic Places.

Holy Cross Church was completed in 1915 as a place of worship for the area's Lithuanian immigrants. Its Baroque style makes it an architectural standout in the region. The church is featured in many books about Chicago architecture.

Constructed in 1871, the First Baptist Congressional Church is featured in many books on Chicago architecture chicago new development condos.

It is an Illinois Historic Landmark and a Chicago Landmark. The church's interior has been imitated by many subsequent church builders in the country.

A Chicago landmark, the Chicago Board of Trade Building is also a National Historic Landmark. The building is well-known for its Art Déco architecture and has even been the site for movie productions. If you can, be sure to take a tour of its interior to witness its gleaming marble surfaces and captivating artwork.

Although many of its buildings have been demolished, Hull House remains an important Chicago landmark. This settlement house was founded by Jane Addams and Ellen Gates Starr in 1889. Many immigrants to the city spent time at the complex that once contained 13 buildings. Today, the Hull Mansion and dining hall are open to the public as a museum.

Formerly known as the AT&T Center, the Franklin Center is located on the west side of the Loop. The 5th tallest building in the city, the Franklin Center is an office building that was completed in 1989. Relatively new to the city skyline, this building is a modern structure boasts a block-long lobby and 650-seat restaurant.

Constructed in 1911, the Chicago and North Western Railway Power House is featured in the distinctive Beaux Art style. Today, the building is used for mixed purposes including commercial space, but it initially was the site for an important area power house. The building was finally awarded Chicago Landmark status in 2006.

The Union Park Hotel is located on the Near West Side and was built in 1930. Its decorative Art Deco style and ornamentation continue to make it an area standout in terms of architectural embellishment.

The Humboldt Park Field House and Refectory and the Boathouse Pavilion are arresting West Side sights. Designed as a "pleasure ground" with lagoons and gardens, the park complex was developed between 1905 and 1920. The park and its structures are listed on the National Register of Historic Places.

Though designed by the father of skyscrapers, architect William LeBaron Jenney, Garfield Park shows the architect's more artful side. The park and its historic structures are located in the East Garfield Park neighborhood. The park's golden-domed administration building and bandshell attract many visitors and fans of historic architecture.

South Side Chicago Architectural Highlights

South Side Chicago Architectural Highlights

As the largest section of the city, the South Side sprawls and, not surprisingly, features many of the city's most important architectural attractions. Don't miss the building highlights on your Chicago architecture tour.

Constructed in 1872, the Second Presbyterian Church of Chicago features the Gothic Revival style of architecture. The church was the place of worship for many of the city's most prominent families and its attendees include Robert Todd Lincoln, the son of Abraham Lincoln. Famous for its remodeled Arts and Crafts interior and illustrious stained-glass windows, the church continues to be a majestic sight. It is listed on the National Register of Historic Places and is a National Historic Landmark.

Located in Bridgeport, St. Mary's of Perpetual Help is a Polish cathedral-style church that dates to 1889. The illustrious church was attended by many of the city's Union Stockyard workers. While the church's exterior is impressive, its interior harbors some significant artworks, some of which were recently restored by the Art Institute of Chicago.

The Field Museum of Natural History is one of the largest museums in the world and was built in 1921. Two million people visit this museum each year. It is renowned for its collections of natural history and world-class exhibits.

The John G. Shedd Aquarium is easily one of Chicago's most notable attractions. An indoor public aquarium located on the shores of Lake Michigan, this aquarium was opened in 1930. Today, it is a National Historic Landmark is celebrated for its diverse range of exhibits. The building itself features Greek-inspired and Beaux Arts architecture.

Soldier Field dominates the area south of the Loop. This immense stadium is home to the Chicago Bears and also features a myriad of events. The stadium opened in 1924 and continues to be a major city attraction for sports fans and music lovers.

Dedicated to the study of astronomy, the Adler Planetarium is perched at the tip of Northerly Island and makes up part of the city's Museum Campus. It is a National Historic Landmark and boasts extensive spaces for exhibitions. The building opened to the public in 1930.

Completed in 1891, the Manhattan Building is a unique structure owing to its many bow windows that provide lots of natural light for the building's interior. This building has the claim-to-fame of being world's oldest surviving skyscraper to feature a completely skeletal support structure. The building's designer, William Le Baron Jenney, would go on to become one of the most important architects to pioneer tall buildings.

If you're touring Jackson Park on the South Side, make your way to the beach to visit the 63rd Street Bathing Pavilion, the oldest and largest beach house in Chicago. Its construction was completed in 1919 and was restored at the beginning of the 21st century. The pavilion continues to be used by beach-goers, boaters, and to house special events and exhibitions.

Harold Washington Library Center

Completed in 1991, the Harold Washington Library Center boasts 756,000 square feet. If possibly, you'll want to venture inside this public building to witness its enchanting Winter Garden located on its 9th floor. The building features 972,000 square feet devoted to the main library's extensive collection and exhibits.

While the near South Side is home to popular attractions, be sure to venture further south and explore the Pullman Historic District. Once the planned town of Railroad tycoon George Pullman, the neighborhood boasts various historic buildings, but its crown jewel must be the majestic Hotel Florence. Constructed in 1881, the Hotel Florence is built in the Gothic Revival style. Be sure to book a tour as the hotel's interior with its bar and period rooms are sure to amaze you.

Constructed for the 1893 World's Columbian Exhibition, the Museum of Science and Industry once housed the exhibition's Palace of Fine Arts and also provided the initial space for the Field Museum of Natural History before it moved to its current building in the city's Museum Campus. Located at 5700 South Lakeshore Drive, the building is one of the South Side's most popular attractions.

Located on the campus of the University of Chicago, Rockefeller Chapel was constructed in 1928. It features many Gothic features and is an imposing structure on the campus grounds. If you can tour the interior, be sure to note its impressive wood carvings.

Designed by famous architect Frank Lloyd Wright, the Robie House is a National Historic Landmark that is situated on the campus of the University of Chicago in the neighborhood of Hyde Park. The house reflects the Prairie School style of architecture and was completed in 1910. Fans of the architect's works are invariably drawn to this notable Chicago attraction.

The John J. Glessner House was designed by architect Henry Hobson Richardson and constructed in 1887. Located at 1800 South Prairie Avenue, this residence boasts an innovative floor plan with its interior courtyard and abundance of natural light—both unusual features for 19th century residential dwellings.

Located in the Beverly neighborhood of Chicago, the Adams House is one of Frank Lloyd Wright's residential constructions. Its Prairie-style design underscores its distinctive look. If you're a fan of Wright's work, you'll want to tour his various city constructions.

The Henry B. Clarke House dates to 1836 and is regarded as the city's oldest surviving home. Part of the Prairie Avenue Historic District, the Clarke House houses a museum and features guided tours.

The Longwood Drive District is a stunning residential street that meanders through the South Side neighborhoods of Beverly and Morgan Park. The street is renowned for its stunning residences that include many historic homes.

Special Features

Dominating the Chicago shoreline is Navy Pier, a 3,300-ft. pier that ventures into Lake Michigan and features about fifty acres of shops, restaurants, parks, exhibition space, and special attractions like its Ferris Wheel and the Chicago Shakespeare Theater. Navy Pier is a popular tourist destination, attracting upwards of 9 million visitors annually.

Located in the middle of Grant Park, Buckingham Fountain is one of the world's largest fountains. It attracts throngs of locals and tourists alike with its majestic display. The fountain was dedicated in 1927 and was inspired by a fountain on the grounds of the Palace of Versailles. Often dubbed the city's "front door," this extraordinary fountain is a landmark you don't want to miss.

These are among the most popular Chicago buildings and landmarks to see as you tour the city. Home to some of the tallest buildings in the world, Chicago features a world-famous skyline that features these buildings against the stunning backdrop of Lake Michigan. If you are searching for a new home in Chicago, a building tour will help you get to know various neighborhoods of the city and the architecture that lends them their distinctive characters. Look for Chicago buildings with roof access or Chicago new development condos that are located in exciting areas of the city. Whether you want to live in an historic structure or a cutting-edge new build, let us know what you're after and we'll help you achieve your real estate goals.

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