53 Best Sights in Chicago, Illinois

Named after former Mayor Richard M. Daley's late wife, this park offers a place to play between Lake Michigan and the city's skyline. Opened in late 2014, it includes 40-foot-high rock-climbing sculptures, an Enchanted Forest with a kaleidoscope and mirrored maze, a Slide Crater, a Wave Lawn, and an area strictly for toddlers. A skating ribbon winds around the park, with ice skates available to rent in the winter months, and rollerblades and scooters in the summer.

Likened to everything from corncobs to the spires of Antonio Gaudí's Sagrada Família in Barcelona, these twin towers were a bold departure from the severity of the International Style, which began to dominate high-rise architecture beginning in the 1950s. Designed by Bertrand Goldberg and completed in 1968, they contain condominiums (all pie-shaped, with curving balconies); the bottom 19 stories of each tower are given over to exposed spiral parking garages. The complex is also home to six restaurants, including the House of Blues, plus Hotel Chicago, a huge bowling alley, and the marina.

Like a slipcover over a sofa, the clean, geometric facade of this 1895 building expresses what lies beneath: in this case, a structural steel frame. Sure, the base is marked with roughly cut stone and a fancy cornice crowns the top, but the bulk of the Marquette Building mirrors the cage around which it is built. Inside is another story. The intimate lobby is a jewel box of a space, where a single Doric column stands surrounded by a Tiffany glass mosaic depicting the exploits of French Jesuit missionary Jacques Marquette, an early explorer of Illinois and the Upper Midwest. From its steel skeleton to the terra-cotta ornamentation, this Holabird & Roche structure is a clear example of the Chicago style.

This massive art deco building takes up nearly two square blocks and was the world's largest building when it opened in 1930. These days the neighborhood landmark is known as ground zero for home-design shopping, with the first floor given over to LuxeHome, a vast collection of high-end kitchen, bath, and building showrooms open to the public. The upper floors are lined with trade-only showrooms.

This legendary outdoor bazaar, which operates every last Sunday of the month from May to October, is part of Chicago's cultural landscape. Relocated by the city amid much controversy in the 1990s as the University of Illinois at Chicago's campus expanded, the market returned to its original location in 2024 and remains a popular spot, particularly for Latino immigrants, to buy and sell wares year-round. The finds aren't so fabulous, but the atmosphere sure is fun, with live blues and stalls peddling Mexican street food.

Built in two segments a few years apart, the Monadnock captures the turning point in high-rise construction. Its northern half, designed in 1891 by Burnham & Root, was erected with traditional load-bearing masonry walls (6 feet deep at the base). In 1893 Holabird & Roche designed its southern half, which rose around the soon-to-be-common steel skeleton. The building's stone-and-brick exterior, shockingly unornamented for its time, led one critic to liken it to a chimney. The lobby is equally spartan; lined on either side with windowed shops, it's essentially a corridor, but one well worth traveling. Walk it from end to end and you'll feel as if you're stepping back in time.

"Contemporary" is generally defined here as work made in the past two or three decades. Curators constantly seek out new talent and underappreciated established photographers, which means that there are artists here you probably won't see elsewhere. Rotating exhibits have included explorations of infrastructure, crime, and American identity.

This 1989 limestone-and-granite edifice by Skidmore, Owings & Merrill looks back to the art deco days without becoming a victim of fashion's past. Four floors of the 38-story tower are dedicated to a radio and television broadcasting facility.

This private university, founded in 1851 by town namesake John Evans, puts Evanston on the map. Its sprawling Evanston campus hugs Lake Michigan. Strolling around its ivy-covered walls while listening to the crashing waves hitting the shore is a delightful experience. The campus is home to highly regarded undergraduate and graduate schools (the Medill School of Journalism and Kellogg School of Management among them) as well as the Block Museum of Art, which has more than 6,000 works in its permanent collection. Northwestern's Big Ten athletics program draws a mix of students and locals to games, especially when the Wildcats football team play.

Old Town was known in the mid-1800s as the Cabbage Patch (for its German immigrant inhabitants’ proclivity for planting, well, you guessed it) and took turns in the 20th century as a stronghold for LGBTQ+ rights and an incubator for artists and comedians. Today the neighborhood feels more polished and less bohemian, but hints of the old world can still be found in the narrow cobbled alleys, the tolling bells of historic St. Michael’s church, and the barroom banter at mainstay Old Town Ale House. Head to Wells Street, the main drag, for independent shops and good bars and clubs (including the famed Second City).

Massive steel Puerto Rican flags proudly straddle the road along this six-block stretch of Division Street in Humboldt Park, marking out the nucleus of Chicago’s large Puerto Rican community. This is the place to be for mofongo and café con leche in easygoing sidewalk cafés. Keep your eyes peeled for murals by street artists and a walk of fame celebrating Puerto Rican luminaries.

There are two architecturally notable buildings at the plaza. Directly west of the Aon Center and across from Millennium Park is One Prudential Plaza. Designed by Alfonso Iannelli and completed in 1955, this limestone-and-ridged-aluminum structure was once the city's tallest building (barring the statue of Ceres atop the Board of Trade). At the time, it had the world's fastest elevators and an observation deck that became passé once some of the city's other behemoths were completed. Attached to One Prudential is its sibling Two Prudential Plaza, nicknamed "Two Pru," a towering glass-and-granite giant with an address of 180 North Stetson Avenue. Along with their neighbors they form a block-long business-oriented minicity. Two Prudential is the tallest reinforced concrete building in the city, and its blue detailing and beveled roof are instantly recognizable from afar.

The clearly expressed, gleaming verticality that characterizes the modern skyscraper was first and most eloquently articulated in this trailblazing steel-frame tower, built by Burnham, Root, and Charles Atwood. Completed in 1895 and now home to the stylish Staypineapple Hotel, the building was a crumbling eyesore until the late 1990s, when the city initiated a major restoration. In the early and mid-1900s, it was a mixed-use office building. Al Capone's dentist reportedly worked out of what's now Room 809. Don't be misled when you go looking for this masterpiece—a block away, at State and Randolph streets, a dormitory for the School of the Art Institute of Chicago shamelessly mimics it. Once you've found the real thing, admire the mosaic floor and ironwork in the reconstructed elevator lobby. The building boasts early examples of the Chicago Window, which define the entire facade by adding a shimmer and glimmer to the surrounding white terra-cotta.

Named for late mayor Richard J. Daley, this boldly plain high-rise is the headquarters of the Cook County court system, but it's best known as the site of a sculpture by Picasso. Simply dubbed the Picasso, this monumental piece provoked an outcry when it was installed in 1967; baffled Chicagoans tried to determine whether it represented a woman or an Afghan hound. In the end, they gave up guessing and simply embraced it as a unique symbol of the city. The building itself was constructed in 1965 of Cor-Ten steel, which weathers naturally to an attractive bronze. In summer, its plaza is the site of concerts, political rallies, and a Thursday farmers' market. In December, Christkindlmarket (a traditional German market selling food and gifts) takes over the area.

A tower, arched doorways, and a large round window form bold masses on the exterior of this church, designed in 1887 by Daniel Burnham and John Root. The Romanesque interior, with vaulted arches, gives a feeling of breadth and spaciousness. The parish was organized to serve Irish workers at the nearby Union Stock Yards.

If you want to see masterpieces but don't want to spend a long day wandering around one of the major art museums, the Smart, which turned 50 in 2024, may be just your speed. Its diverse exhibition program features art from around the globe.

Listed on the National Register of Historic Places, this opulent clubhouse on Lake Michigan is one of the last remaining Mediterranean resort-style buildings in the Midwest. Referred to by many as the "Gem of the Southside," the posh country club looks like something out of an F. Scott Fitzgerald novel. It boasts meeting rooms, stables where the Chicago Police Department's horses are quartered, a 9-hole golf course, and a beach with newly built concessions. With magnificent crystal chandeliers, balconies, pillars, and a vaulted ceiling, its ballrooms and grand lobby wow visitors, including President Barack Obama and First Lady Michelle Obama, who chose the center for their wedding reception. 

From 1899 to 2007 this was the flagship location for the department store Carson, Pirie, Scott & Co. The work of one of Chicago's most renowned architects, it combines Louis H. Sullivan's visionary expression of modern design with intricate cast-iron ornamentation. The eye-catching rotunda and the 11 stories above it are actually an addition Sullivan made to his original building. In later years D.H. Burnham & Co. and Holabird & Root extended Sullivan's smooth, horizontal scheme farther down State Street. The ground floor now houses a Target, with office tenants occupying the floors above.

Built in 1894 with a courtyard and annexes constructed in 1911 and 1912, the nation's oldest surviving artist studios have been restored and designated a Chicago landmark. Shops, galleries, and event spaces now fill the studios.

For a glimpse of how the working class lived at the turn of the 20th century, head south of Wicker Park to the Ukrainian Village. In its center, on Haddon Avenue and on Thomas and Cortez streets between Damen Avenue and Leavitt Street, you'll find a well-preserved group of workers' cottages and apartments. At the corner of Leavitt and Haddon Streets, gilded cupolas mark Holy Trinity Orthodox Cathedral (tours offered occasionally; schedule at  holytrinitycathedral.net), an early-20th-century church designed by renowned Chicago architect Louis Sullivan.

Running along both sides of Wabash Avenue from Ida B. Wells Drive south to 16th Street, this mile-long stretch is an outdoor gallery of murals and street art. There are nearly 40 permanent installations and an evolving set of temporary exhibitions. Chicago artists including Shepard Fairey, Hebru Brantley, and Sam Kirk have had work shown here.

Water is still pumped to some city residents at a rate of about 250 million gallons per day from this Gothic-style structure, which, along with the Water Tower across the street, survived the 1871 conflagration. Lookingglass Theatre, located in the same complex, has called this place home since 2013.

This triangular little patch of green, donated to the city in 1870 by politician Charles Wicker, is a neighborhood favorite and home to softball fields, a children's water playground, a dog park, and outdoor movies. The handsome central fountain is a great spot for chilling out and people-watching in warm weather.