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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 Adler Planetarium is a must-visit spot for astronomy enthusiasts and those interested in space exploration. Founded by philanthropist Max Adler in 1930, it was the first planetarium built in the Western Hemisphere and remains the oldest. The planetarium boasts three full-size theaters, including the Sky Theater planetarium, where visitors can enjoy various shows and presentations about the night sky. The Sky Theater projector can recreate every aspect and movement of the night sky, giving visitors an incredibly realistic experience. The Definiti Space Theater, an addition made in 1999, comes equipped with a digital full-dome video environment for an immersive experience. Visitors can also enjoy sculptures outside the planetarium, such as the "Man Enters the Cosmos" sundial and a statue of renowned astronomer Nicholas Copernicus. The lobby's dedication plaque is also a work of art, depicting the gods and goddesses that represent each planet, except for Pluto, which had yet to be discovered at the time of the plaque's creation.

The Ravinia Festival is a popular event that attracts over 600,000 visitors annually. The festival takes place from June to September at Ravinia Park, which hosts 120 to 150 music events. The Breaking Barriers Festival is part of a successful series of concerts and symposiums focusing on female conductors. This time, the festival celebrated female composers in classical, jazz, and singer-songwriter genres. The festival featured three evening concerts, panel and roundtable discussions, workshops pairing composers and conductors, and other events collaborating with New Music USA and The Chicago Network.

Bike and Roll Chicago offers several locations to rent bicycles or Segways to explore the city. They provide five different tour options, such as The Amazing Lakefront, Friendly Neighbors, Chicago River & Parks, The Presidential Tour, and Bikes @ Nite, so you can pick the one that best suits your interests. Join one of their award-winning bike tours and see all the top attractions in Chicago. Glide along the stunning lakefront on a Segway. Please wear appropriate walking shoes as you embark on a magical adventure through downtown Chicago, lit with beautiful illuminations.