Alexandra Marks

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.

The hidden garden behind the Lincoln Park Conservancy is a must-visit spot. The Alfred Caldwell Lily Pool, situated in this garden, is designed to resemble a river flowing through a prairie. Walking along the stone path that encircles the lily pool, you'll come across a pavilion, a council ring, and native plants seen from mid-April to mid-November. As soon as you enter through the Prairie-style Fullerton gate, you will find yourself surrounded by a serene and beautiful garden filled with the soothing sounds of birds chirping and a gentle waterfall. Alfred Caldwell, a landscape architect, designed this garden as a hidden treasure for the people of Chicago. The gravel pathway on the east side of the Lily Pool site is partially accessible for those with disabilities. However, the stone pathway on the west has some steps up and down, making it less accessible. Visitors should also be aware that both sides of the path have a slight incline and decline, which should be considered while exploring the garden.