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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.

Enjoy a memorable evening on the water with City Experiences Chicago Cruises, Boat Rides & Tours. With a perfect setting to enjoy dinner, drinks, and dancing, they provide stunning views of Chicago from the water. City Experiences offers exciting options for groups of 20 or more, such as historic sightseeing cruises in Boston, thrilling speed boat rides on Seadog in Chicago or Codzilla in Boston, and awe-inspiring whale watches in San Diego or Boston. With unique tours and experiences, City Experiences ensures an unforgettable day on the water.