The 50 most beautiful buildings in Chicago: 30–21

We searched Chicago's skyline from the skyscrapers to the side streets (and beyond) to find our favorite examples of the city's architectural excellence

1/10

Two Prudential Plaza

2/10

333 West Wacker

3/10

Unity Temple

4/10
Humboldt Park Boathouse
5/10
© City of Chicago / GRC

Chicago Cultural Center’s Preston Bradley Hall

6/10
Photograph: Kristine Kuczora
Hotel InterContinental
7/10
Marquette Building
8/10
Photograph: Daniel X. O’Neil

Harold Washington Library

9/10
Photograph: Daniel Schwen
Lake Point Tower
10/10
Photograph: Annie Evans / Chicago Architecture Foundation

Santa Fe Building

Two Prudential Plaza

Completed in 1990

We’ve called its sibling, One Prudential Plaza, one of downtown’s ugliest buildings, but “Two Pru,” with its shiny glass and granite, soaring chevron setbacks and pyramid crest ending in a pointy spire, feels like a cross between the Chrysler Building and a rocket ship next to its squat older brother. It’s easy to gaze up from the lawn at Pritzker Pavilion on a summer evening and imagine it blasting off.

Fun fact Two Pru’s concrete structure won an award from the Structural Engineers Association of Illinois in 1995.

333 West Wacker

Completed in 1983

A favorite on river cruise architecture tours, this modern office tower uses its spot on the river’s bend to beautiful advantage, with its northwest face a smoothly curved curtain of green glass that catches the light and gorgeously reflects the sky, water and the buildings across the river. On the building’s entrance side, the crown is distinctively serrated. The design made stars of the young firm behind it, Kohn Pederson Fox, which eventually designed both of 333’s immediate neighbors, 225 West and 191 North Wacker.

Fun fact 333 West Wacker was featured in Ferris Bueller’s Day Off as the location of Ferris’s dad’s office.

Unity Temple, 875 Lake St, Oak Park

Completed in 1908

Frank Lloyd Wright described the Unity Temple as his “contribution to modern architecture,” a stark concrete structure that was highly unorthodox at the time of its construction. Oak Park’s Universalist congregation asked Wright to design the church after the group’s original church burned down in 1905. Inspired by the principals of the Universalist faith, Wright created a largely unadorned building with separate areas for worship and social functions. The building became a National Landmark in 1971, but preservationists are still struggling to raise funds to repair the structural damage that has plagued the building.

Fun fact The thick concrete walls of this church were designed to shield worshippers from the noise created by nearby streetcars and trains.

Humboldt Park Boathouse, 1301 N Sacramento Ave

Completed in 1906

Designed by Frank Lloyd Wright contemporary Hugh Garden, the Humboldt Park Boathouse is a textbook example of Prairie School architecture. Situated on the banks of a lagoon, the horizontal structure echoes the flat landscape of the park, featuring an open-air pavilion that allows the surroundings to become a part of the building. Originally a storage facility for row boats and a gathering place for concerts and events, the boathouse fell into disrepair before the city deemed it a historic landmark and helped fund its restoration. Today, it’s a popular destination for wedding photographers and architecture tours.

Fun fact The boathouse used to be flanked by a music courtyard where bands would perform, but it was turned into a parking lot when automobiles became popular.

Chicago Cultural Center, 78 E Washington St

Completed in 1897

After the Great Chicago Fire decimated the city’s public reading room, England donated 8,000 books to the city, necessitating the construction of a building to hold them. Inspired by the neo-classical architecture of the buildings constructed for the World’s Columbian Exposition in 1893, Chicago’s first public library was designed by Boston-based architectural firm Shepley, Rutan and Coolidge, which had just finished the original Art Institute building. Completed in 1897, the ornate granite and limestone structure features marble halls and a Tiffany glass dome that is 38 feet in diameter, the largest of its kind. When the library’s collection was moved to the Harold Washington Library in 1991, the building became the Chicago Cultural Center, a free museum and arts center.

Fun fact It took almost a year for 70 men to drive 2,357 wooden piles 75 feet into the clay below the site’s soil, creating the structure’s foundation.

Hotel InterContinental, 505 N Michigan Ave

Completed in 1929

The Moorish yellow dome is a tip-off that this building has Shriner roots. Originally the home of the Medinah Athletic Club for those fez-wearing, tiny-bike-riding Shriners, the building was purchased by InterContinental Hotels in 1988. The building’s original features were painstakingly restored, including the four-story lobby and the 14th-floor indoor pool—if Spain’s Alhambra had a junior Olympic–sized swimming pool, it would look something like this.

Fun fact Look up just after you walk through the Michigan Avenue entrance; the Shriner greeting "Es salumu Aleikum" ("Peace be to God") is carved into marble between two columns.

Harold Washington Library, 400 S State St

Completed in 1991

During Harold Washington’s tenure as mayor, Chicago finally settled on a permanent location for the library’s flagship branch, which had been in temporary quarters since 1977, when the Chicago Cultural Center took over the building. A 1988 design contest resulted in a plan incorporating design elements from nearby buildings like the Rookery and the Monadnock along with acroteria (those big green sculptures on the roof), which depict owls, a symbol of knowledge.

Fun fact When it opened in 1991, the Harold Washington Library was the largest public city library in the world.

Marquette Building, 56 W Adams St

Completed in 1895

This handsome 19th-century example of the Chicago School is now home to the John D. and Catherine T. MacArthur Foundation, which oversaw a restoration a decade ago. Its dark brick and terra-cotta façade is pleasingly structured, showing the bones of its steel skeleton. But much of the beauty is in the details: Bronze relief sculptures over the entrance depict the travels of Father Jacque Marquette and Louis Joliet. The revolving doors lead to a two-story lobby marked with busts of Marquette, Joliet and their party as well as chiefs of important Native American tribes, all designed by Edward Kemeys; the balcony railing is home to Tiffany mosaics of further scenes from the explorers’ trek.

Fun fact Kemeys also designed the Art Institute’s lions.

Lake Point Tower, 505 N Lake Shore Dr

Completed in 1968

Looking up at the gleaming tower it can be hard not to get distracted by dreams of what it might be like to live inside the luxurious condo building (movie stars have frequently been housed here while filming in the city), which boasts a shocking list of amenities including a third-floor park, indoor and outdoor pools, and even an on-site dentist. Thanks to its unique shape and the fact that it’s the only skyscraper in the city located east of Lake Shore Drive, it boasts fabulous views from every unit of both the Chicago skyline and Lake Michigan. The building is perhaps most striking in direct sunlight, when the bronze-tinted glass and gold-anodized aluminum in its façade reflect the rays and transform its dark exterior into a golden tower.

Fun fact Architects George Schipporeit and John Heinrich were students of Ludwig Mies van der Rohe, and the building was inspired by his 1922 design for glass-curtained skyscraper in Berlin.

Santa Fe Building, 224 S Michigan Ave

Completed in 1904

This 17-story office tower, also known as the Railway Exchange Building, looms large over Michigan Avenue. Designed by Daniel Burnham’s firm, the building's white terra-cotta façade is ridged with rows of bay windows that give it visual texture; the top of the building is marked by a ring of circular portholes underneath the cornice. The iconic Santa Fe sign facing the lake that topped the building for decades was replaced in 2012 by the logo of one of its current tenants, Motorola.

Fun fact Burnham moved his own office into the building, and developed his Plan of Chicago on the top floor.

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