164 Best Sights in Chicago, Illinois

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).

Fans of The Wizard of Oz love getting up close with Dorothy, Toto, and all the other beloved characters assembled here in sculpture form. Author L. Frank Baum lived in Chicago at the turn of the 20th century. The park also has a flowery Emerald City Garden and play lot for pint-size visitors.

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.

On the northwest corner of Astor and Burton places in the swanky Gold Coast, you'll find this Georgian building. It was commissioned in 1891 by Chicago Tribune chief Joseph Medill and built by Stanford White. You can't go inside, though, because it's been converted into condos.

Walk among over 1,000 tropical butterflies and learn about the impact of rivers and lakes on daily life at this modern, light-washed museum. Like Chicago's other science museums, this one is perfect for kids, but even jaded adults may be excited when bright yellow butterflies land on their shoulders. The idea is to connect with nature inside without forgetting graceful Lincoln Park outside. Interesting temporary exhibits round out the offerings.

Four pillars carved with dragon designs adorn the entrance of this beautifully landscaped park, which is named for Chinatown's most renowned civic leader. Wedged within the shadows of railroad tracks and highways, its 17 serene riverside acres include a children's playground, winding walking trails, a fieldhouse, and a boathouse (kayak rentals are available at the last of these in summer). A large yellow-and-red pagoda provides good views of the looming Chicago skyline to the north; March through December, you can also board a water taxi here for a scenic—and cost-effective—ride to the Loop.

The Chicago metro area has the largest Polish population of any city outside Warsaw, and this museum celebrates that fact. Take a trip to the old country by strolling through exhibits of folk costumes, memorabilia from Pope John Paul II, and the reconstructed rooms of famed pianist and statesman Ignacy Paderewski. There's also Hussar armor and an 8-foot-long sleigh in the shape of a dolphin. Chat up the knowledgeable docents and you might be treated to tales of Paderewski's romances or the exploits of the progressive 13th-century queen Jadwiga. 

Built in 1891, the simple, redbrick Pontiac is an early Chicago School skyscraper—note the classic rectangular shape and flat roof. It is the city’s oldest existing Holabird & Roche building.

Bounded by Ida B. Wells Drive on the north, Polk Street on the south, Plymouth Court to the east, and the Chicago River to the west, this district fell into disrepair in the 1960s, but a neighborhood resurgence began in the late 1970s. Bibliophiles flock in for the Printers Row Lit Fest, a weekend-long literary celebration held each September. But, at any time of year, you can admire examples of buildings by the group that represented the First Chicago School of Architecture (including Louis Sullivan).

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.

One of Chicago's African American cornerstones, this church was founded in 1847 and served as an Underground Railroad stop. The present building, designed by Henry Starbuck, opened in 1891, and the rough-finished brick exterior is in keeping with the time. The interior has a tin ceiling and simple stained-glass windows. Many notable people have addressed the congregation, including President William B. McKinley, Booker T. Washington, and Dr. Martin Luther King Jr.

This famed indoor-outdoor flea market, held on the last Saturday and Sunday of the month from late March through mid-December, is Chicago's answer to London's Portobello Road Market. Centered on Randolph Street and Ogden Avenue at Plumber's Hall, it offers midcentury furniture, vintage handbags, ephemera, and much more. May through September, free shuttles head back and forth between the Hall and Water Tower Place on the hour, from 10 to 3.

If you enjoy music under the stars, the outdoor concerts at Ravinia are a stellar treat. Ravinia Festival, a summer-long series of performances, is the hot-months' home of the Chicago Symphony Orchestra, but the festival also features popular jazz, chamber music, rock, pop, and dance acts. Pack a picnic, bring a blanket or chairs, and sit on the lawn, often for little more than the cost of a movie. Large screens are placed on the lawn at some concerts so you won't miss anything. Seats are also available in the pavilion for a significantly higher price. There are restaurants and snack bars on the park grounds, so if you forget your goodies you still won't go hungry. Concerts usually start at 7 or 8 pm; the park usually opens two to three hours ahead to let everyone score spots and get settled. Weekend-morning concerts are aimed at kids. They feature a "KidsLawn" with an interactive music experience, and on select dates an "instrument petting zoo," arts and crafts, and live performances. During the off-season, check out the Fall and Spring Series of indoor concerts at Bennett Gordon Hall.

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.

Curious about how the wealthy built their urban palaces during America's Gilded Age? Steps away from the Magnificent Mile, the former Samuel Mayo Nickerson mansion has lavish interiors with 19th-century furniture and objets d'art, including pieces by Louis Comfort Tiffany and George Schastey, along with rotating exhibitions related to art, architecture, and design.

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.

North of the Merchandise Mart and south of Chicago Avenue, between Orleans and Dearborn, is a concentration of art galleries carrying just about every kind of work imaginable. Virtually every building on Superior Street between Wells and Orleans houses at least one gallery, and visitors are welcome to stop in. Free tours leave from Addington Gallery at 704 N. Wells on the second Saturday of the month at 11 am; galleries also coordinate their exhibitions to showcase new works typically on "First Fridays" (check the Chicago Gallery News for dates). Although many artists have left this high-rent district for the less expensive, more industrial West Town, there is still a lot to see here, just a 10-minute walk from Michigan Avenue.

A former tannery set on a three-acre lot alongside the Chicago River has been repurposed as an evolving hub for neighborhood tastemakers. The lofty brick space is home to a small-batch whiskey distillery (Judson & Moore) with a stylish tasting room, a shoe boutique, and a ceramics center with some single-session classes. Toward the back, Soul & Smoke serves excellent barbecue (the brisket's a don't-miss), while the riverside patio and small marina out back double as a launch for Chicago Electric Boat Company, which rents retro-looking "donut boats" by the hour (from $152) for impromptu river cruises.     

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.

Constructed in 1874, this handsome Gothic Revival church was designed by James Renwick, also the architect of the Smithsonian's Castle and New York City's St. Patrick's Cathedral. The National Historic Landmark features one of the largest collections of Tiffany stained-glass windows anywhere.

Completed in 1923 and built to accommodate the area's growing number of Italian immigrants, this church is the oldest continuously operating Italian American church in Chicago. Its Romanesque Revival style was popular with the famous church architects Worthman and Steinbach, and its interior is filled with statues and striking stained-glass windows. 

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.

Opened in 1924 as the Municipal Grant Park Stadium, the facility was renamed in 1925 to commemorate American soldiers who died during World War I. Just south of the Museum Campus, the building and its massive columns are reminiscent of ancient Greece. It's the home field for the NFL's Chicago Bears and Major League Soccer's Chicago Fire FC, as well as a venue for college games and concerts. A controversial modern glass expansion, which looks like a spaceship that landed on the arena, was completed in 2003. Behind-the-scenes tours feature the Doughboy statue, Colonnades, the field, South Courtyard, visitors' locker room, the suites, and the United Club.

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. 

The Southport Corridor, as this stretch of pavement is known, is lined with independent shops and high-end boutique chains to serve the area's well-dressed urban professionals with money to burn. Those stores are peppered amongst neighborhood pizza joints and classic taverns, bookended by music venue Schubas Tavern to the south and the historic independent movie theater The Music Box at the north. 

This gorgeous Greek Revival building, erected in 1910, has an equally lavish interior. It was originally the Anshe Sholom Synagogue.

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.

Now home to the acclaimed Chicago Symphony Orchestra (CSO), this complex includes Orchestra Hall, built in 1904 under the supervision of Daniel Burnham. The Georgian building has a symmetrical facade of pink brick with limestone quoins, lintels, and other decorative elements. An interior renovation, completed in 1997, added a seating area that is behind and above the stage, allowing patrons a unique vantage point.

In the mid-19th century, when Italians started to migrate to Chicago, about one-third of them settled in and around Taylor Street, a 12-block stretch between Ashland and the University of Illinois at Chicago. It is best known for its Italian restaurants, though Thai food, tacos, and other ethnic options are here, too.

A few blocks east of 18th Street's hustle and bustle, this neighborhood landmark was built in 1892 but shuttered for decades, and reopened as a stunning multipurpose space in 2013. The focal point is a concert hall, elegantly fashioned after a Prague opera house, which hosts a broad range of musical performances and artsy events. Punch House, a hip and moodily lit lounge for the cocktail crowd, and Tack Room, a cocktail bar featuring live music in the former carriage house, are also on the premises.