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Last-minute location details and surprise menus are just part of the thrill of these covertly operated eateries.
Some are easier to get into than others, but once you’re in, you’re in -- and, to your date, instantly impressive.
Skip having to spend money on someone you just met with Free Thursdays at the Art Institute of Chicago (you like free stuff, right? Heads you’re taking the CTA, tails you’re taking a cab.
) -- which will both make you seem cultured and give you plenty to talk about. For every decision you need to make, take turns flipping.
Visit Headquarters Beercade or Emporium for arcade games, or Guthries Tavern for good, old-fashioned board games, all with great beer options.
Take a moment to enjoy the beauty that Chicago has to offer, then learn how to start your career as a beekeeper or get your hands dirty at one of Garfield Park’s compost tutorials. Go ahead and visit some of the area's other amazing parks.
It’s also just formal enough to feel each other out, and just cozy enough to, uh, feel each other out.Finish off with a nightcap downstairs at modern-day piano lounge Tack Room or the basement-level Punch House, where live DJs and expertly crafted cocktails ensure good vibes.Get up close and personal while cooking side-by-side at The Chopping Block.If the date is going well, walk across the street to The Gage to continue the conversation. In addition to making decision-making a cinch, it’s a surefire way to learn just how spontaneous your plus-one really is.If your date is a dog owner, head to one of the city’s many canine-friendly parks like Wiggly Field Dog Park in Lincoln Park or Montrose Beach in Uptown for a few rounds of fetch before topping it off with happy hour at Filini, where guests can bring their pups to the patio on Wednesdays for a menu featuring the likes of “Bad to the Bone Burgers” and “Frosty Paws” ice cream.
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From improv shows and ice cream crawls, to Segway tours and staycations, here are the best ways to woo a significant other in the Second City now.