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The Hideout is not your typical bar; it's a place where everyone is welcome, regardless of whether they fit in. This prohibition-era bar may be small, but it's been a community space for independent music and performance in Chicago for over 25 years. On Saturdays, you can enjoy live music and dancing at The Hideout. It's a hub for music, art, performance, plays, poetry, rock, and rebellion. The bar is rooted in complex, hard-playing, creative artistic expression and intellectual freedom. It's more New Deal than New Age, and while it's not for everyone, it's for anyone who wants to experience something unique and authentic.

If you are a fan of blues music, you should visit Kingston Mines during your trip to Chicago. This jazz and blues bar is one of the oldest establishments in the city and offers an intimate setting for live music performances. The venue has been presenting the best acts since 1968 and has a legendary reputation for hosting some of the finest live music performances in Chicago. It has won the "Best Blues Club" award at the Chicago Music Awards for 13 years. At Kingston Mines, you can enjoy live, authentic jazz and blues music on two stages. The venue also offers a wide selection of drinks, including beer buckets, wine, and cocktails. And if you're feeling hungry, check out Doc's Rib Joint - the in-house restaurant that serves mouthwatering barbecue, chicken, burgers, seafood, ribs, and various tasty sides and appetizers.

The 360 Chicago Observation Deck is a must-visit attraction for anyone looking to enjoy a stunning 360-degree view of Chicago's Magnificent Mile. Located at 1,000 feet, the observation deck provides breathtaking panoramic views of the city and surrounding areas. You can see up to 80 miles and four neighboring states from the lookout. For those not afraid of heights, the deck also features Chicago's only open-air skywalk, which offers a thrilling sensation of looking down. While enjoying the breathtaking views of the city, you can relax and sip on a refreshing drink. Additionally, the observation deck offers TILT, the highest thrill ride in Chicago.

If you want a unique entertainment experience in Chicago, consider visiting the historic Chicago Theatre. The theatre has been restored to its former glory and is now a popular venue for concerts and shows. It features a French Baroque design, crystal chandeliers, ornate artwork, and other decadent details. The iconic marquee of the theatre symbolizes the city and has been featured in countless works of art, photography, television shows, and movies. Apart from its rich history and stunning architecture, the Chicago Theatre is also a famous venue for live performances. It has hosted various events, including stage plays, magic shows, stand-up comedy, and musical acts. Many favorite artists have performed on its stage, including Frank Sinatra, Dolly Parton, Prince, and Kanye West, to name just a few.