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.And while there’s no shortage of romantic spots and activities in this sprawling town, sometimes we all need a little help coming up with something novel, thrilling, or downright out there to help bring us a little closer to that (potentially) someone special.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.Grab a stack of singles and head to some of the city’s premier photo booths to document your date progress.Start with live music and live action shots at Schubas before trying your hand at scenario snaps at Quimby’s Bookstore, Beauty Bar, and Empty Bottle before closing out the night at Skylark.
Attend Adler Planetarium's After Dark event (21 ) on the third Thursday of each month to enjoy cocktails and one-of-a-kind views of the Chicago skyline.
They've got one of the largest dark liquor selections in the neighborhood, plus a pretty sweet fireplace.
It’s also just formal enough to feel each other out, and just cozy enough to, uh, feel each other out.
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.