6 Best Sights in Chicago, Illinois

Hunkered down across from Grant Park, this 110,000-ton granite-and-limestone behemoth was an instant star when it debuted in 1899, and it didn't hurt the careers of its designers, Dankmar Adler and Louis H. Sullivan, either. Inside were offices, a 400-room hotel, and a 4,300-seat state-of-the-art theater with electric lighting and an air-cooling system that used 15 tons of ice per day. Adler managed the engineering—the theater's acoustics are renowned—and Sullivan ornamented the space using mosaics, cast iron, art glass, wood, and plaster. During World War II the building was used as a Servicemen's Center. Then Roosevelt University moved in and, thanks to the school's Herculean restoration efforts, the theater is again one of the city's premiere performance venues. Tours are offered most Sundays, Mondays, and Wednesdays.

When it opened in 1921, the grand and glitzy Chicago Theatre was tagged "the Wonder Theatre of the World." Its exterior features a shrunken version of the Arc de Triomphe, and its lobby is patterned after the Royal Chapel at Versailles with a staircase copied from the Paris Opera House. Murals decorate the auditorium walls and ceiling. The seven-story, 3,600-seat space has served as a venue for films and famed entertainers ranging from John Philip Sousa and Duke Ellington to Ellen DeGeneres and Beyoncé. Tours let you stand on the stage where they performed, go backstage, and peruse its autographed walls.

On Monroe, near State Street, the ornate CIBC Theatre (formerly the Bank of America Theatre and before that the LaSalle Bank Theatre and the Shubert Theatre) stages major Broadway plays and musicals. It was the tallest building in Chicago when it opened in 1906.

The handsome home of the Lyric Opera of Chicago and the Joffrey Ballet is grand indeed, with pink-and-gray Tennessee-marble floors, pillars with carved capitals, crystal chandeliers, and a sweeping staircase to the second floor. Designed by Graham, Anderson, Probst & White, the second-largest opera house in North America combines lavish art deco details with art nouveau touches. Tours are given a few times a year.

An opulent "hasheesh-dream decor" of Buddhas and elephant-type chairs made the erstwhile Oriental Theatre a popular spot for viewing first-run movies starting in 1926. Though listed on the National Register of Historic Places in 1978, the building continued to crumble for some time after. In 1998 it was restored to its past splendor and since then has had a second life as a home to Broadway shows; it was rechristened for the late patriarch of the Nederlander family of theater producers in 2019.

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.