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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.

Chicago Jazz Festival invites you to a four-day celebration of jazz featuring world-class artists. The festival is free and open to the public and will take place at Millennium Park, downtown Chicago, the Chicago Cultural Center, and various venues across the city. The Labor Day weekend festival aims to promote all forms of jazz and showcase Chicago's local talent alongside national and international artists. The event seeks to raise awareness and appreciation for one of the city's most beloved art forms. As the only jazz organization in Chicago that offers a wide range of opportunities for artists, both old and new, they provide high-visibility venues for creating and performing new work. They collaborate directly with Chicago Public School teachers to develop programs for their students and professional development for themselves. Additionally, they present the city's most significant artists in their communities, building an audience that crosses racial and geographic boundaries to break through historical barriers that have been obstacles to the evolution of music.