The iconic Vanna Venturi house in Chestnut Hill was designed by Philly starchitect Robert Venturi for his mother and built in 1964. It’s often considered the first post-modern home in the country and has been named one of the 10 Homes that Changed America. It has oddly fascinating features like a pitched roof, random curves, and a staircase that leads to nowhere. Today, it has a new owner and is listed on the Philadelphia Register of Historic Places.

Of all of Louis Kahn’s few and far between residential designs, the Margaret Esherick House in Chestnut Hill is perhaps his most iconic. Kahn designed the one-bedroom home for Esherick in 1959. It’s a 2,500-square-foot concrete-and-stucco rectangle, with a flat roof and a wall of windows in the two-story living room. Today, it is home to new stewards who restored the modern home from top to bottom.

The Fisher Fine Arts Library stands out on Penn’s campus, thanks to its fiery red brick facade and its jaw-dropping interiors. Designed by Frank Furness between 1888 and 1890, the library’s soaring reading room made a prominent cameo in the Tom Hanks movie Philadelphia. It’s been praised by modern architects like Robert Venturi, as well as Louis Kahn, who chose to teach his studios at PennDesign here instead of in the design school next door.

The 30th Street Station we know today is considered one of the last-remaining grand train stations in the U.S. Built between 1929 and 1933, it was designed by Graham, Anderson, Probst and White with a neoclassical exterior and Art Deco details within. The main concourse stretches the length of two football fields and its 95-foot tall ceilings are no doubt the most striking features of the train station. Despite its iconic look, the structure is being renovated and should see some contemporary updates soon.

The 29-story Cira Centre earns a spot on this list because it was the first new building to pierce to sky west of the Schuylkill River in 2005. Designed by Pelli Clarke Pelli, the glassy, diamond-like structure has four sides at its base and six at the top. While no longer the tallest building in University City (that honor goes to its neighboring FMC Tower), it’s fare to say that the Cira Centre kicked off the development boom of the neighborhood and its ever-changing skyline.

In 1893, the city decided that it was time to build a new art museum. It chose to build the Philadelphia Museum of Art on the hilltop of Fair Mount, and tasked prominent architect Horace Trumbauer to design it. Much of the design, however, can be owed to Trumbauer’s partner Julian Abele, the first African-American graduate of the University of Pennsylvania’s architecture program. Built in 1928, it is a monumental work of architecture, made even more famous in modern times for its prominent role in the Rocky movies. The museum is currently undergoing a $196 million renovation led by Frank Gehry

This colossal Gothic Revival prison in Fairmount is steeped in history, and when it opened in 1829 it became one of the most famous and expensive prisons in the world and the first penitentiary in the country. Designed by architect John Haviland, Eastern State Penitentiary was groundbreaking in that it was the first prison designed to make prisoners feel true regret and penitence for their crimes. The penitentiary sat on 11 acres of farmland called Cherry Hill. Today, the historic landmark is open for daily tours year-round and nightly tours during the Halloween season.

The glossy new Comcast Technology Center just opened this year, with designs meant to complement its neighbor, the original Comcast Center. Whereas the OG center saw a super industrial, contemporary design, this one brings a little more nature and creativity to its spot. The first floor lobby is covered in wood, with live trees growing in the middle. Plants decorate the walls of a cafeteria upstairs, and colorful murals run throughout the upper floors. Plus, it’s all topped off with a Four Seasons hotel—and stunning, 360-degree views—at the very top.

The Cathedral Basilica of Saints Peter and Paul at Logan Square holds the title of being the largest brownstone structure in the entire city, as well as the oldest building on the Parkway (It was one of the few buildings that weren’t demolished to make way for the Parkway.) Open since 1894, the basilica was designed by local architect Napoleon LeBrun, who was only 25 at the time. The interiors, considered some of the most beautiful in the city, feature murals, mosaics, and stained glass windows by Constantino Brumidi.

One Liberty Place will go down in history as the first building to dethrone Philadelphia’s City Hall as the tallest edifice in Philadelphia. When it was built in 1987, One Liberty Place became the first skyscraper to break the so-called gentleman’s agreement that no building should ever surpass the height of the William Penn statue atop City Hall. The 61-story tower was designed by Helmut Jahn and has been compared to the Chrysler building in New York City.

Designed by Rafael Viñoly Architects, the Kimmel Center for the performing arts was built in 2001 at the height of the city’s plan to create a performing arts district along South Broad Street. The showstopper on Broad wows with its barrel-vaulted glass roof, which features a an expansive terrace beneath. Though it has not gone without its critiques, the Kimmel Center remains one of the standout buildings along the Avenue of the Arts.

Today, it’s simply referred to as the Bellevue, but when it opened as a hotel in 1904, it soon earned the nickname “The Grand Dame” of Broad Street. The Bellevue-Stratford Hotel was designed by G.W. and W.D. Hewitt, with an ornate French Renaissance facade, a slate mansard roof, and 1,090 guest rooms. It even debuted with light fixtures designed by Thomas Edison. The hotel has hosted more than a dozen presidents and dignitaries—it even managed to survive a 1977 outbreak of Legionnaires disease. Today, it is home to a Hyatt Hotel, offices, and retail.

Designed in 1871 and built five years later, the Historic Landmark Building at the Pennsylvania Academy of the Fine Arts is considered by some as the first modern building in America. Designed by Frank Furness and George Hewitt (they parted ways a year before the building opened in 1876), it resembles a jewel box both inside and out and is a lesson in functionality, heavily influenced by the industrial boom that Philadelphia was relishing in at the time.

The former Parker-Spruce hotel certainly has a sordid past. The building has been around for 100 years, and was a popular spot for boxers and jazz musicians to stay during the early 1900’s. It’s also seen some not-so-great guests, and a whole ton of lore. Nevertheless, the building is an iconic piece of Philadelphia’s history and the history of the Gayborhood where it stands. Recently, it’s changed hands and undergone a massive renovation, as the new owners hope to breathe new life into the towering structure.

Today, the 33-story tower at 1200 Market is a Loews Hotel. But when it opened its doors in 1932, it was heralded as the country’s first International-style skyscraper and home to PSFS. Architects George Howell and William Lescaze were encouraged by PSFS bank president James M. Willcox design something "ultra-practical" and modern. Indeed, it was the second building in the country to have central air-conditioning. Although it now serves as a hotel, much of the original, high-end finishes and details remain, including custom Cartier clocks in the lobby and above the elevators. Its PSFS signs atop the building remain just as iconic as ever.

No list of iconic Philadelphia buildings would be complete without Independence Hall, the very place where our country was founded in 1776. Master builder Edmund Woolley is considered responsible for the design of Independence Hall, which is a great example of Georgian architecture, while Andrew Hamilton oversaw the construction, which ran from 1732 to 1748. Fun fact: The original designs did not include a steeple—this was added in 1750. Independence Hall (known then as the State House) served as the country’s capitol for 10 years before it moved to Washington.

What would this list be without The Bourse, a stunning—and historic—stone structure right in the heart of Old City? Built in the late 1800s, The Bourse was originally a commodities exchange, but has since changed hands several times. In the 1980’s it got a food court (and very ‘80s) interior makeover, and became a hotspot for tourists stopping in for a bite while traversing the historic neighborhood. But recently, it’s seen another change—one that aims to restore it to the historic beauty it once had, with bright white walls and contemporary food stands, the new building tries to draw in tourists and locals alike.

This trio of 31-story residential towers was part of an urban renewal effort led by city planner Edmund Bacon in the early 1960s. I.M. Pei won the competition, designing these identical apartment buildings along with low-rise townhouses nearby. The towers were notable not just for their sheer size amid a neighborhood of 18th- and 19th-century rowhomes, but also their floor-to-ceiling windows and poured-in concrete facades.