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If you're a fan of Shakespeare, you should attend the Chicago Shakespeare Theater on Navy Pier. This professional theater company was founded in 1986 by Barbara Gaines and is the third largest in the Midwest. They produce works from the Shakespeare canon and other theatrical performances, with over six hundred performances annually at the Courtyard Theater and the Upstairs space. The theater has won numerous awards, including 36 Joseph Jefferson Awards, three Laurence Olivier Awards, and a Regional Theatre Tony Award. The theater also has a family series for younger audiences and special student pricing.

Celeste is an exceptional twist on the traditional American drinking establishment, consisting of four unique levels that architecture, art movements, social clubs, and the blurring of boundaries between art and life inspire. The fine dining and imaginative cocktails perfectly complement the thoughtfully designed space. What sets Celeste apart is that a talented ensemble cast collaborates to create an unparalleled experience. The vintage glow of the building, which was initially a glass factory, adds a nice touch. There are four levels, each with a unique ambiance - Cocktail Bar, Deco Supper Club, Disco, and Garden. The Whiskey Bar on the first floor is perfect for a casual evening with friends. In contrast, the Deco Supper Club on the second floor provides a glamorous throwback to Chicago's architectural history. The third-floor Disco promises to be fun, and the fourth-floor Garden offers a beautiful escape with its retractable glass rooftop and Victorian furniture.

The Adler Planetarium is a must-visit spot for astronomy enthusiasts and those interested in space exploration. Founded by philanthropist Max Adler in 1930, it was the first planetarium built in the Western Hemisphere and remains the oldest. The planetarium boasts three full-size theaters, including the Sky Theater planetarium, where visitors can enjoy various shows and presentations about the night sky. The Sky Theater projector can recreate every aspect and movement of the night sky, giving visitors an incredibly realistic experience. The Definiti Space Theater, an addition made in 1999, comes equipped with a digital full-dome video environment for an immersive experience. Visitors can also enjoy sculptures outside the planetarium, such as the "Man Enters the Cosmos" sundial and a statue of renowned astronomer Nicholas Copernicus. The lobby's dedication plaque is also a work of art, depicting the gods and goddesses that represent each planet, except for Pluto, which had yet to be discovered at the time of the plaque's creation.