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The 50 most beautiful buildings in Chicago: 20–11

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

Chicago Temple Building
 (Photograph: Max Herman)
Photograph: Max Herman
Chicago Temple Building
 (Photograph: Steven Green)
Photograph: Steven Green
Wrigley Field
 (Photograph: Tom Rossiter, � University of Chicago)
Photograph: Tom Rossiter, � University of Chicago

Reva and David Logan Center for the Arts, University of Chicago

Thalia Hall
 (Photograph: Courtesy of Studio Gang)
Photograph: Courtesy of Studio Gang

Aqua Tower


John Hancock Center

 (Photo: Jason Smith)
Photo: Jason Smith

Interior of the Mansueto Library at the University of Chicago

 (Photograph: Michael Barera)
Photograph: Michael Barera
Mansueto Library at University of Chicago
35 East Wacker (a.k.a. The Jeweler’s Building)
Rookery Building
Chicago Temple Building, 77 W Washington St

Chicago Temple Building, 77 W Washington St

Completed in 1924

This 23-story sacred space is home to the First United Methodist Church of Chicago, the oldest church in the city—it has occupied this spot on the corner of Washington and Clark Streets since 1838. Constructing this skyscraper—the tallest building in the city from its completion in 1924 until it was surpassed by the Board of Trade in 1930—was a statement of its commitment to the city amid pressure to move to the suburbs. Its spire and enormous steeple, done in a Neo-Gothic style similar to Tribune Tower, which was finished the year after the Temple Building, serve as a beacon standing sentry over Daley Plaza.

Fun fact Most of the building’s floors are rented as office space, with the proximity to government offices making it popular with lawyers; Clarence Darrow once had an office on the sixth floor.

Wrigley Field, 1060 W Addison St

Wrigley Field, 1060 W Addison St

Completed in 1914

The Friendly Confines is celebrating its 100th birthday this year (making it six years younger than the Cubs’ last championship). As the neighborhood around it has evolved, the park has, too—including, in recent decades, the controversial installation of lights in 1988, the bleacher expansion in 2005 and the tackiness of the “Captain Morgan Club.” And the current Cubs owners, the Ricketts family, appear likely to continue pushing for revenue-generating “modernizations.” But like its baseball club, Wrigley remains lovable—and we’d argue it’s because of the interplay between its history and its environs.

Fun fact It’s the oldest surviving National League ballpark, giving fans a taste of baseball’s golden age from seats that offer a view of both the legendary ivy and a thriving surrounding neighborhood instead of a sea of suburban parking lots.

Reva and David Logan Center for the Arts, 915 E 60th St

Reva and David Logan Center for the Arts, 915 E 60th St

Completed in 2012

Of the three structures that make up this modernist cluster of the University of Chicago, it’s the Jenga-like limestone tower that draws the eye and wins a place on this list, not its lower siblings with the sawtooth solar and green rooftops. The overall look is stereotypical of today, all sharp angles and eco-consciousness, to the point of looking ripped from the pages of Dwell or Monocle. But there’s also the look of a child’s toy or a puzzle, as if it were designed by Lego. It announces that you’re going to get heady arts with a playful spirit.

Fun fact The $35 million donation by Reva and David Logan is believed to be the single largest cash gift to the arts in the city of Chicago.

Thalia Hall, 1807 S Allport St

Thalia Hall, 1807 S Allport St

Completed in 1892

In 2013, Thalia Hall opened as home to Dusek’s Board & Beer and Punch House and, in 2014, the building opened its concert space. Great idea, right? John Dusek had a similar idea in the 1890s, when he created Thalia Hall to showcase entertainers from Bohemia, as Pilsen had a huge Bohemian population (the neighborhood is named for the second-largest city in Bohemia, now the Czech Republic). The space, designed by the architectural firm of Faber and Pagels, still has its original ceilings and light fixtures. The building has also included a movie theater, community gathering space, apartments and retail.

Fun fact The building is modeled after the Prague opera house and named for the Greek muse of comedy.

Aqua Tower, 225 N Columbus Dr

Aqua Tower, 225 N Columbus Dr

Completed in 2009

Is there a more appropriately named skyscraper? Concrete balconies ripple like foaming waves over the sea-blue glass on Jeanne Gang’s award-winner. The sinuous projections also recall topographic maps and those cardboard dinosaur skeleton kits you get at the Field Museum. Studio Gang’s masterpiece (to date) announces that the future is going to not only be better for the environment, but better for the eye and imagination as well.

Fun fact The underground garage features the city’s first public electric car charging stations.

John Hancock Center, 875 N Michigan Ave

John Hancock Center, 875 N Michigan Ave

Completed in 1969

The John Hancock Center, which towers over Streeterville, has offices and residences plus television and communications equipment, and retail, but it’s best known for the 94th-floor observatory, where you’ll find Tilt, the simultaneously cool and terrifying new feature that tips you out 1,000 feet above the city. Want to bypass the line? Head up to Signature Room at the 95th, a bar and restaurant, where you’ll get the same view and a drink.

Fun fact The building’s base used to be covered in marble, but it was replaced with gray granite in 1994. Before the marble was removed, the building was compared to a tuxedoed man wearing white socks.

Joe and Rika Mansueto Library, 1100 E 57th St

Joe and Rika Mansueto Library, 1100 E 57th St

Completed in 2011

Standing in stark contrast to the brutalist architecture of the nearby Regenstein Library, this striking domed structure brings a touch of modernity to the University of Chicago campus in Hyde Park. The only part of the $81 million structure that most visitors will ever see is the naturally lit reading room, which allows students to study beneath the sky. But the elliptic dome is just the tip of the library: The majority of the structure is subterranean, housing up to 3.5 million books in five floors of storage space that are accessible via an automated retrieval system that can produce a book in five minutes or less.

Fun fact All of the glass located more than 18 feet above ground is coated with tiny ceramic dots that reduce the glass’s transparency, making it more visible to birds.

35 East Wacker (a.k.a. The Jeweler’s Building)

35 East Wacker (a.k.a. The Jeweler’s Building)

Completed in 1927

Originally erected to cater to the city's diamond jewelers, this building has a few notable features, including the Father Time clock and the dome on the roof, but its most intriguing feature hasn't existed for decades. The former Jeweler's Building used to contain an auto elevator that traveled up to the 22nd floor, allowing its tenants to travel safely to their office without fear of having their precious bags of gems stolen. These days, the unique exterior of Joachim G. Giaver and Frederick P. Dinkelberg's structure can be found in film and TV, including Batman Begins, Transformers: Dark of the Moon and The Good Wife.

Fun fact Al Capone was a frequent patron of the Stratosphere Lounge, a restaurant that was once located in the building's dome.

Monadnock Building, 53 W Jackson Blvd

Monadnock Building, 53 W Jackson Blvd

Completed in 1893

Its thick, curving exterior and rust-brown brick are stunning but, for us, it’s the interior of the Monadnock that makes it special. Pull open the heavy wood-and-glass doors and you’re transported to the 1890s. The businesses on the first floor all have gorgeous wood doors with brass knobs and the name of the store written in gold on glass. Its mosaic tile floor gleams. Filament bulbs hang from brass light fixtures on the ceiling. Ornate silver metalwork adorns the first-floor staircase. It’s by far the most gorgeous way to walk from Jackson to Van Buren.

Fun fact Monadnock is the name of a mountain in the developers’ native New England.

Rookery Building, 209 S LaSalle St

Rookery Building, 209 S LaSalle St

Completed in 1888

The warm, reddish-brown exterior of The Rookery instantly sets it apart from the surrounding Loop skyscrapers. Look closer and you'll find beautiful details in the columns and windows where architects Daniel Burnham and John Root drew from multiple architectural styles. Burnham and Root must have been proud of the building, as they set up shop in it to plan the 1893 World's Columbian Exposition. The breathtaking light court was updated by Frank Lloyd Wright in 1905 and features an impressive glass ceiling, marble columns and sweeping staircases.

Fun fact It's the oldest standing skyscraper in the world.