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Dating in Chicago

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Singles in nearby cities:
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5 date ideas in Chicago

  1. The Art Institute of Chicago - Tour the Art Institute of Chicago (Bonus tip: Every Thursday from 5 p.m. – 8 p.m., admission is free to Illinois residents!) This place will inspire conversation as you browse through one of the country’s largest art museums.
  2. The Lincoln Park Zoo - Go from the concrete jungle to the animal kingdom in mere minutes. You’ll have to spring for parking, but admission to the zoo is free. Get lost in an oasis of adventure and animals without leaving town.
  3. The Chicago Public Library - Make your date a page-turning one. With regular published authors as guests discussing a variety of topics, enjoy some free entertainment at the CPL that will undoubtedly give you plenty to talk about afterwards.
  4. Guthrie’s Tavern - Not just a neighborhood watering hole, this place offers good food, great microbrews and a chance to challenge your date to a fun board game of Scrabble or Trivial Pursuit. The friendly crowds and cozy and relaxed vibe may make this your favorite hot spot.
  5. Millennium Park - Head over to Pritzker Pavilion and catch a free concert. Don’t forget to bring a picnic basket and your favorite bottle of wine for an unforgettably romantic evening for two.
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