164 Best Sights in Chicago, Illinois

This 50,000-square-foot food hall sports a rotating roster of counter-service stalls, representing 18 hand-picked Chicago eateries. Collected under one roof along with three bars, an outdoor terrace, and a working demo kitchen for chef-driven classes, it's a sort of EPCOT Center of Chicago food for those who don't have time to visit many different neighborhoods.

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.

Modern and contemporary art fans with an interest in the artistic achievements of the Ukrainian diaspora head to this small museum at the far western edge of the Ukrainian Village. One of its two galleries is dedicated to changing exhibitions; the other features the museum's permanent collection of mixed media, sculpture, and painting from the 1950s to the present. Some of the most interesting works are kinetic steel-wire sculptures by Konstantin Milonadis, the constructed reliefs of Ron Kostyniuk, and painted wood structures by Mychajlo Urban. 

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.

At the intersection of Calumet Avenue and Cullerton Street is another of the area's great mansions, which was nearly replaced by a parking lot before it was saved and painstakingly restored in the late 1990s. Today it's a boutique hotel with the same name.

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.

Just outside the Lawrence train station a large sign heralds upcoming bands—who play metal, mariachi, and much more—in a dreamy, Moorish-style ballroom that was built in 1926.

The strip from Lake Shore Drive to Sheffield has an entirely different character than the residential streets nearby. Yes, it has Starbucks and Potbelly, but funky shops, tattoo parlors, and vintage-clothing stores add an interesting, eclectic feel. Just past the El tracks at Sheffield, you'll see the Vic Theatre. Once a luxurious vaudeville venue, it's now a popular spot for live music; on Brew & View nights, when multiple bars are open and the mood is most festive, on-stage acts are replaced by movie screenings.

If you like sweets or have kids in tow, keep an eye out for this bakery, which stocks a mind-boggling array of treats.

Two- and three-story gray-stone houses and other residential buildings line the quiet, leafy side streets heading east and west of Boystown. Wandering along them, you might even feel transported back in time to 1920s or '30s Chicago. In 2008 a stretch of Newport Avenue between Clark and Halsted was temporarily transformed into a cobblestone thoroughfare for the John Dillinger flick Public Enemies, starring Johnny Depp.

South of the Aragon is the marquee of the Riviera Theatre, a rock and pop venue renowned for its mosh-pit diving patrons.

The Chicago Sun-Times Building was torn down to make way for this 92-story tower, which was designed by Skidmore, Owings & Merrill and opened in 2008. A spire that elevates its height to a whopping 1,392 feet makes it the city's second-tallest building. The concrete-reinforced structure (the former Sears Tower and John Hancock Center are reinforced by steel) is a glassy, tiered monolith whose biggest attribute is an idyllic riverfront location. Although there's no viewing deck, the public can get picturesque views of downtown through the floor-to-ceiling windows of its 16th-floor restaurant, Sixteen, or the Terrace (open seasonally); Rebar, on the mezzanine level, provides lovely views of the Chicago River and Michigan Avenue Bridge.