February 14th is approaching fast, so if you’re still deciding what would make the perfect Valentine’s Day date, look no further! Our Chicago dating guide takes advantage of the city’s unique offerings, from the natural scenery to the night life of River North. Whether you’re a local or you’re planning a romantic getaway, we have the perfect Valentine’s date in Chicago for you.

Chicago Skyline

Romantic Evenings

Scoot in close and watch the candles burn as you absorb each other’s presence and Chicago’s unique culture.

  • Dinner on the water. Take advantage of Chicago’s two most beautiful features, Lake Michigan and the skyline after dark.  Board the Odyssey, a luxury yacht, for a three-course dinner and dancing. Or hire a Knock Out charter to dine and explore the river at your own speed. Either way, you’ll be charmed by the lights on the water. For those partial to seasickness, there are several restaurants that overlook the river or look towards the city from Navy Pier.
  • Broadway and dine. Broadway in Chicago brings NYC to “the Loop” all year around. Grab tickets to a musical, or any other play downtown.  The Theater District is also full of fine restaurants, perfect for either a pre-show dinner or a post-show drink. Some even offer parking and valet deals with show tickets (a hot-commodity being that you’re in the center of the city!).
  • Cozy speakeasies. Dark, cozy, and shadowed, speakeasies provide the perfect excuse to sit with your thighs pressed together and forget about the world. Start the night off with underground restaurants like Hi Five Ramen (be in line before 5:30 to avoid an hour wait) or the glamourous Untitled Supper Club. Then switch to intimate bars like The Violet Hour (which most nights is identified only by the line) or Bordel known for its live entertainment.

Daytime Adventures

Not everyone is a night owl, so instead you can plan a day date! Sunlight and movement release endorphins, lifting moods to bring you closer together.

Chicago Botanical Garden
  • See Chicago with new eyes. Play tourist and learn something together! The Chicago Architecture Foundation has detailed tours on part of Chicago even residents miss, from the underground pedway system to the architecture treasures you can only see on the L. For the foodies, check out any of the chocolate, beer, coffee, or pizza tours. Or get a little more excitement by learning about Chicago’s gangster history.
  • Chicago museums. Museums are the perfect excuse to walk slowly, hand in hand, away from the Chicago wind chill. Thankfully, several of Chicago’s museums are offering free admission on Valentine’s Day, or on the weekends before and after. Grab your partner and have fun finding your favorite fish in each tank at the Shedd Aquarium or debate which baby penguin is cuter at Brookfield Zoo.
Dinosaur Skeleton at Museum

Uniquely Chicago

There’s no city like the Windy City. Take your date to the city’s highlights for an experience you can’t find anywhere else.

  • Improv Comedy. Chicago is known as a hub for comedy, especially improv thanks to being a home for Second City. For Valentine’s Day, go for something just as funny but a touch more romantic with The Improvised Shakespeare Company at the IO Theater. Two acts, in the style and theme of the bard, but completely made up on the spot. If you want something a little less highbrow, head to the Under the Gun Theater.
  • Skyscraper Views. The Willis Tower’s Skydeck is open till 8pm in February, giving perfect sunset views. Or, if you’re in the mood for food, you can have breakfast on the famous 103th floor. 360 Chicago, the John Hancock’s option further north, brings a DJ to the observation deck Thursday evenings to complement the Architect’s Corner Café and Bar. To avoid the tourists at the expensive of a lower view point, consider the Wit Hotel’s roof top bar. Close to the river, you can wave at the boats floating by below.

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