Also known as "The Bean,” Millennium Park’s Cloud Gate sculpture is Chicago's most recognizable, and often photographed, pieces of public art since its installation in 2006. Designed by British artist Anish Kapoor, the 66-foot-long polished metal piece casts a wide-angle reflection of the downtown skyline and is impossibly fun place to take selfies.

South of Cloud Gate is Millennium Park’s iconic Crown Foundation, designed by artist Jaume Plensa and Chicago-based Krueck and Sexton Architects. The work features a pair of LED-clad towers that cycle through roughly 1,000 individual faces which spout water through their mouths during the summer. The reflecting pool between the structures is a favorite place for kids to play.

The two bronze lions outside of the Art Institute of Chicago are the city's oldest pieces of public art (don’t worry, they’ll remain while the museum considers a massive renovation). Designed by sculptor Edward Kemeys, the big cats have stood guard along Michigan Avenue since 1894. Today, the Art Institute dresses the iconic sculptures up for holidays and in the gear of Chicago sports teams during playoff runs.

Set back from Michigan Avenue in the South Garden of the Art Institute, this 1913 fountain by sculptor Lorado Taft features five bronze nymphs that symbolize the Great Lakes. Water cascades from shells held by each figure, representing the flow of water from Lake Superior to the Saint Lawrence Seaway. Originally positioned along the building’s southern wall, the fountain moved in 1963 from the West Side of the Art Institute’s new Modern Wing.

It’s incredible that Chicago has a 50-foot original Pablo Picasso sculpture right in the middle of Daley Plaza. However, at the time of its 1967 debut many Chicagoans were critical of the avant-garde, abstract piece calling it an insect and a baboon. Over the years, people grew to love “The Picasso,” and has developed into one of the great symbols of Chicago.

Across the street from Picasso, is another well regarded artist’s work. Look between the Cook County Administration Building and the Chicago Temple to find a sculpture created by notable Spanish artist Joan Miró. The tall figure with a little red mosaic seat at the base was designed in 1981, just two years before his death.

Located in the plaza at the base of Chase Tower, this colorful mosaic was completed by surrealist painter Marc Chagall in 1974. As its name implies, the four-sided piece depicts the arrival of spring, summer, winter, and fall. A 1994 renovation added a protective glass canopy above Chagall’s work.

Alexander Calder’s Flamingo was unveiled in Chicago’s Federal Center Plaza in 1974, although the artist’s signature indicates it was completed one year prior. The steel sculpture features a bright red coloration that stands out against the dark backdrop of its modernist neighbors. Calder’s creation has made appearances in numerous movies, most notably acting as the backdrop for the scene in Ferris Bueller's Day Off where Cameron and Sloan discuss life after high school.

This 30-foot-tall sculpture of Ceres, the goddess of grain, stands 45-stories in the air atop of the Art Deco Chicago Board of Trade building. Designed by John H. Storrs in the 1930s, the figure holds wheat and corn as a reference to the commodities being exchanged on the trading floors below. According to local legend, Storrs designed Ceres with no face, assuming no future building would ever rise high enough to notice.

Art on The Mart is the largest permanent digital art installation of its kind in the world. Using 34 projectors, Obscura Digital and architecture firm Valerio Dewalt Train Associates have transformed the limestone facade of the Merchandise Mart into a 2.5-acre canvas for digital expression. Although it debuted in late 2018, Art on The Mart has already made itself into a entertaining spectacle that can be admired from the Riverwalk.

At the far south end of Grant Park is Agora, an eerie installation of 106 disembodied metal legs. Installed in 2006, the nine-foot sculptures come from Polish artist Magdalena Abakanowicz who has explored the theme of crowds based on her experiences during World War II and Soviet occupation. The Chicago Park District describes Agora as the most important and extensive sculptural installations in Chicago’s recent history.

Designed by architects Louis Sullivan and Dankmar Adler, this ornate terra cotta archway stands at the northwest corner of the Art Institute as the most famous surviving fragment of the grandiose Chicago Stock Exchange building. Built in 1893, the Loop structure was demolished in 1972 to the alarm of preservationists. Five years after the destruction, the arch was moved outside the Art Institute which houses a replica of the Trading Room from the building.