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.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.
You’re limited in what you can do since you are far apart but you have to keep the romance and excitement alive.(And make sure to lock down your babysitter or nanny ahead of time so you don't have to scramble last-minute.)Keep in mind that your date doesn't have to be expensive.We reached out to Ben Homan (relationship blogger at Top Date Ideas), Stef Safran (matchmaking expert of Stef and the City), and Kalyn Brooke Comings (deals expert at Creative Savings), and put together 101 unique and cheap date ideas to get you started.(You can even do some of these at home, while your kids are sleeping!Everyone has a favorite childhood (or adulthood) game, whether it's Monopoly, Clue, or Catch Phrase, so settle in for the night and enjoy a little friendly competition.Or you might try one of the new, more complex games that are sweeping the country like "Settlers of Canaan."Urbanites, toss a blanket and bottle of wine in the car and then drive until you find a scenic location far from the city lights.With gorgeous skylines, prime lakefront access, a vibrant and always-growing food and drink scene, and a population of nearly 3 million, Chicago is arguably one of the best cities for dating.