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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 Illinois Railway Museum is where you can learn about the history of railway transportation and its impact on the country. The Museum houses over 400 pieces of original equipment from when railroad transportation was essential for industrial purposes and everyday life in America. These pieces of equipment include horsecars, steam locomotives, and passenger cars. The Museum also exhibits and operates restored rolling stock and equipment on a demonstration rail line. Moreover, it collects, preserves, and maintains a reference library of publications, technical information, and other materials related to railroads, railways, and transportation for research and other purposes.