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.Chicago has no shortage of skyline views, but the one from Cindy’s at the Chicago Athletic Association -- complete with vistas of Millennium Park, Lake Michigan, and the Jay Pritzker Pavilion -- has date night written all over it.Kick off the night with a round of Chicago-style dogs at Superdawg, then make your way over to Southport Lanes -- one of the few bowling alleys that still uses human pinsetters.
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.Or other "paint dates" like Soul Impressions or Arts n Spirits, all of which let your creativity flow like BYOB wine.At this point, you’ve gotten to know each other a little better and the atmosphere is still intimate enough that you can chat while painting.Tip: Although shisha is quite different from tobacco, make sure your date isn't devoted to maintaining perfectly pink lungs before making any reservations.
Turn up the fun factor by challenging your date to a game.
For the not-so-musically-inclined, hit Movieoke at The Whistler on the first Monday of every month, where instead of song lyrics, you'll be quoting your favorite movie scenes on stage.
Just stay away from anything from Grab a blanket, pack some snacks, bring a bottle of wine, and kick back on the lawn.
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.
If both of you channeled Michael Jackson and Madonna growing up, Danny’s -- a neighborhood favorite for cheap drinks and up-all-night dancing with throwback '80s and '90s tunes -- is a must-visit for testing out your moves together.