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The Steppenwolf Theatre Company is a prestigious theater situated in Chicago. It was established in the early 1980s by Gary Sinise, Terry Kinney, and Jeff Perry. The theater has staged numerous timeless plays such as "Grease," "The Glass Menagerie," "Orphans," and "The Grapes of Wrath," to name a few. The Steppenwolf Theatre Company is widely known for its exceptional performances. It has received numerous prestigious awards, including the Tony Award for Regional Theatre Excellence and the National Medal of Arts. Additionally, the company's apprenticeship program is recognized as one of the Top 10 Internships in America by the career website Vault.com. If you are a theatre fan, visit the Steppenwolf Theatre Company for an unforgettable live entertainment experience.

If you want to have a good laugh and witness some of the best comedic talents in the show business, you should visit The Second City Theater. This theater has been the breeding ground for many famous comedians like John Belushi, John Candy, Bill Murray, Dan Aykroyd, Gilda Radner, Mike Myers, Chris Farley, Steve Carell, Stephen Colbert, and Tina Fey. The Second City is an improvisational comedy company that started in Chicago. The company has stages in Toronto and Los Angeles, 11 touring ensembles, and training centers and programs in other cities. The performances are semi-improvised and feature scripted material with new content added after the second act, often based on audience suggestions

The Chicago Athenaeum Museum of Architecture and Design is an international museum in Chicago known for its 20th-century architecture. The Museum is dedicated to showcasing the key features and history of the city's architecture, as well as the early examples of modern technological inventions such as the telephone, television, toaster, and other appliances. Its mission is to educate the public about the value of good design in all areas of the discipline, including architecture, industrial and product design, graphics, landscape architecture, and urban planning. The Museum emphasizes how design can positively impact the human environment, from the "spoon to the city."

Chicago Jazz Festival invites you to a four-day celebration of jazz featuring world-class artists. The festival is free and open to the public and will take place at Millennium Park, downtown Chicago, the Chicago Cultural Center, and various venues across the city. The Labor Day weekend festival aims to promote all forms of jazz and showcase Chicago's local talent alongside national and international artists. The event seeks to raise awareness and appreciation for one of the city's most beloved art forms. As the only jazz organization in Chicago that offers a wide range of opportunities for artists, both old and new, they provide high-visibility venues for creating and performing new work. They collaborate directly with Chicago Public School teachers to develop programs for their students and professional development for themselves. Additionally, they present the city's most significant artists in their communities, building an audience that crosses racial and geographic boundaries to break through historical barriers that have been obstacles to the evolution of music.