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The best places for a first date, according to Chicagoans

From a Cubs game to karaoke, here are the best first date destinations.

Isaiah Reynolds
Written by
Isaiah Reynolds

No matter what anyone says, Chicago is a city of love. We even illuminate the city skyline in red and pink hues for Valentine’s Day! It can, however, get a little boring going to the same places over and over again for dates (and if anyone on a date says they know a “special spot,” it’s always, without fail, just the lakefront). Looking to switch up where to go on a first date? We asked Time Out Chicago readers on Facebook and X to share their favorite destinations. Locals got pretty passionate about their recommendations—below are some of the best (and most interesting) places for a first date according to Chicagoans.

Where to take Chicagoans on a first date:

  • Cindy’s Rooftop.
  • “Wrigley Field Cubs Game.” Who said a Chicago-style hot dog and pint of Old Style wasn’t romantic?
  • “A stroll along the Chicago Riverwalk.”
  • “Apparently, the Smart Museum of Art and the Medici Cafe. At least it worked for me. Married 10 years!” Taking diligent notes.
  • The Green Mill.
  • “In the summer a water taxi from downtown to Chinatown for lunch.”
  • The Neofuturists and a drink at Hopleaf.”
  • Kibbitznest. Bond over books and brews with your boo.
  • “Art institute followed by a Cubs game - if they're disinterested in either one, move on.” Still taking diligent notes.
  • Ping Tom Park in Chinatown. Perfect spot for post-boba tea views.
  • Reggie’s Rooftop.
  • Trivoli Tavern.
  • Karaoke at Alice’s Lounge. Don’t let anyone tell you that belting out a power ballad on a first date is moving too fast.
  • Old Irving Brewery.
  • “Lower Wacker anywhere.” No comment.
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