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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 Auditorium Theatre of Roosevelt University is an incredibly historic venue that is worth a visit. This entertainment space has been around for over a century. It has hosted various performances, from classical orchestras like the Chicago Symphony Orchestra to legendary rock acts like Jimi Hendrix, Pink Floyd, and Eric Clapton. As a National Historic Landmark and a Chicago Landmark, the Auditorium Theatre is an integral part of the city's history. It was once home to the Chicago Symphony Orchestra and the Chicago Civic Opera. After reopening in 1967, it quickly became a premier venue for rock stars like Janis Joplin, Bob Marley, and many others. If you find yourself in Chicago, a trip to the Auditorium Theatre is a must-see. Not only is it a beautiful and historic venue, but it's also an essential part of the city's cultural heritage.

If you're looking for a romantic date spot in Chicago, consider ROOF on theWit. This lounge within the Wit Hotel offers a breathtaking city view from its outdoor patio and hangover space. Whether you're in the mood for steak or pizza, their dinner menu offers a wide range of delicious entrees. ROOF is a luxurious retreat that can be found on the 27th floor, offering unique hand-crafted cocktails, delectable cuisine, stunning views of the skyline, and vibrant design and entertainment. It has been crowned Hotel Bar of the Year by the Nightclub & Bar Awards and recognized by Travel+Leisure as one of the top 3 rooftop bars in the world. Guests can indulge in the finest acoustic music series, world-class DJs, and live runway shows.