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The Lyric Opera of Chicago is known for its visually stunning productions each season, featuring some of the world's greatest singers. The company has gained international fame for its artistic excellence, celebrated orchestra, and chorus. The live performances of the Lyric Opera of Chicago are powerful, unique, and inspiring to audiences, leaving a lasting impression long after the curtain falls. Additionally, the Lyric Opera of Chicago fosters creativity by providing innovative learning opportunities, creative exploration, and artistic collaboration. The company encourages tens of thousands of students, educators, and families from across Chicago to embrace the joy, power, and relevance of opera as a catalyst for growth and change.

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.

The Wells Street Art Festival is an annual event on the second weekend of June. It is located in Old Town's popular Wells Street corridor and attracts around 50,000 visitors yearly. The festival showcases talented artists from across the continent specializing in traditional painting, sculpture, artisan woodworking, metalsmithing, jewel crafts, digital arts, and more. Additionally, there is a dedicated performance stage where local musicians, performance artists, and cover/tribute bands entertain the crowd throughout the weekend. Moreover, at the corner of Wells Street and Evergreen Street is a children's play area where kids can participate in arts and crafts, watch a performance, or have fun. The festival also has over 20 food and drink vendors who sell a variety of tasty treats. Visitors can try something from all the excellent Old Town restaurants participating.