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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.

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.

Old St. Patrick's Church is a historical landmark in Chicago that was designed to withstand the test of time. Built in the 1850s, it is among the few structures that survived the devastating Great Chicago Fire of 1871. The church's architecture is rooted in the Celtic Revival movement, making it an outstanding example of Chicago's unique architectural style. Today, Old St. Patrick's Church is a vibrant community of more than 3,000 members, warmly welcoming visitors from diverse backgrounds. Located at the intersection of Chicago's diversity, the church celebrates its rich historical legacy while looking toward a promising future. Apart from Sunday masses, the church organizes guided tours and annual block parties, fostering community and joyous celebration.