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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.

The Chicago Athenaeum Museum of Architecture and Design is an international museum in Chicago known for its 20th-century architecture. The Museum is dedicated to showcasing the key features and history of the city's architecture, as well as the early examples of modern technological inventions such as the telephone, television, toaster, and other appliances. Its mission is to educate the public about the value of good design in all areas of the discipline, including architecture, industrial and product design, graphics, landscape architecture, and urban planning. The Museum emphasizes how design can positively impact the human environment, from the "spoon to the city."