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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.

Hawthorne Race Course is a venue that offers both live racing and simulcasting. It is a thoroughbred horse racetrack with a one-mile dirt oval and a seven-furlong turf oval. The homestretch on the main track is 1,320 feet long, making it one of the longest in the country. Founded in 1891, Hawthorne Race Course is the oldest sporting venue in Illinois for horse racing, considered America's original sport. The business is family-owned and operated, now in its 4th generation, and has been hosting racing events on the City's border for over a century. The track is famously known as "Chicago's hometown track." Hawthorne is also the only race course in the nation that hosts both Thoroughbred and Standardbred racing. Additionally, they have the largest network of off-track betting bars in Illinois and offer two PointsBet Sportsbooks and a sportsbook at the track.

If you're a fan of blues music, you will want to attend Buddy Guy's Legends in Chicago. This iconic blues bar is owned by the legendary blues musician Buddy Guy himself, and it's one of the best places in the country to catch a live blues performance. Over the years, some of the biggest names in music have graced the stage at Buddy Guy's Legends, including Van Morrison, Bo Diddley, The Rolling Stones, Lou Rawls, ZZ Top, John Mayer, Stevie Ray Vaughan, and many more. It's a must-visit spot for music lovers visiting Chicago.