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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 Shedd Aquarium is a magnificent destination for those interested in exploring marine life without diving into the water. The exhibits and attractions have won numerous awards. The aquarium has five permanent exhibits: Amazon Rising, Caribbean Reef, Waters of the World, Oceanarium, and Wild Reef. It houses a diverse collection of animals and marine life, including over 1,500 fish species, mammals, birds, reptiles, amphibians, and insects. The Shedd Aquarium houses around 25,000 fish and animals, including various fascinating creatures such as sea otters, beluga whales, sea turtles, penguins, sharks, octopi, and jellyfish. Additionally, you can also find Pacific white-sided dolphins, Australian lungfish, Grand Cayman blue iguanas, sea lions, cow-nose rays, dragon moray eels, moon jellies, red-bellied piranhas, sea cucumbers, zebra sharks, and sea stars at the aquarium.

If you're a fan of Shakespeare, you should attend the Chicago Shakespeare Theater on Navy Pier. This professional theater company was founded in 1986 by Barbara Gaines and is the third largest in the Midwest. They produce works from the Shakespeare canon and other theatrical performances, with over six hundred performances annually at the Courtyard Theater and the Upstairs space. The theater has won numerous awards, including 36 Joseph Jefferson Awards, three Laurence Olivier Awards, and a Regional Theatre Tony Award. The theater also has a family series for younger audiences and special student pricing.