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Chicago's Best First Date Spots

Posted on February 6, 2024   |   Updated on September 30, 2025
Simone Alicea

Simone Alicea

A person takes a photo of Chicago's skyline with lots of clouds in the background

Chicago’s skyline looking dreamy 😍 (Chris Sweda / Tribune / Getty)

City Cast

Alphabet Dating with a Chicago Twist

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With Valentine’s Day around the corner, love is in the air. That’s why we’ve got you covered with meals that will impress and date ideas to help you get to know that new special someone.

Best on a Budget

Show your date the stars at Adler Planetarium, which is open late and free for Illinois residents on Wednesday nights. For a daytime option, go to the Garfield Park or Lincoln Park conservatories instead of buying flowers.

Best to Impress

Learn your date’s niche interest, then find the Chicago museum dedicated to it. Bugs? The Insect Asylum in Avondale. Music? Find exhibits on post-punk in Bridgeport, hip-hop in Bronzeville, and more. Classic cars? Yup, in Belmont Cragin.

City Cast

Who Can Plan The Best Chicago Alphabet Dates?

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Best for Competitive Types

Use games to break the ice. Emporium and Replay are arcade bars with multiple locations. Or if you’re feeling more adventurous, try throwing some axes in West Loop.

Best for Creative Types

Color Cocktail Factory in Pilsen offers several artistic options from the classic sip-and-paint to date night pottery. Bonus: You’ll always have the art to remember your date!

Best for a Chill Night

Drinks may be a classic first date, but it’s not always easy to find a bar that’s not too loud, easy to get to, and with a good drink to boot. We got you: Try Long Room in North Center or Open Outcry Brewing in Morgan Park.

💖 Plus, even more date ideas

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