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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.

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.