Whether you want to plan an unforgettable, casual or unique first date, there are many places to meet Chicago singles and break the ice around the Windy City. We’ve got you covered with Chicago dating ideas and the ins and outs of impressing that special someone you met on the Chicago dating site.

Get Artsy While You Sip


Kick off the night by creating a fun and sophisticated art party with Bottle & Bottega, a unique art space that swirls creative juices with a glass of wine for inspiration. Everyone can be an artist here. Here’s how it works: artists of any skill level can sign up for a painting class which will be guided by a local artist. No need to worry about the art supplies, it’s all provided. Then uncork your wine and your creativity with your date.


Get A Little Bougie


Really show off your sophisticated side with a casual and refreshing twist at Bourgeois Pig, a cozy café lined with books, 18th century décor, chess games, and a literary inspired menu that will make you giggle. There’s amazing outdoor seating and it’s close to the Lincoln Park Zoo and the lake. — perfect for a stroll afterwards.


Out-of-This-World Date Night


Why not let the stars guide your date night at the Adler Planetarium and Astronomy Museum. You don’t have to be a sci-fi geek to appreciate the permanent exhibit “A Journey with Jim Lovell”. It also has state-of-the-art exhibits like interactive computers in the CybeSspace Gallery and virtual reality experiences in the space theater. The setting is unreal. And once you’re done exploring the universe, head over to Sullivan’s Steakhouse nearby. The swanky supper club features one of the city’s best strip steaks. There’s also jazz performed nightly.




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