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Three Dots and a Dash and Lost Lake are among the most famous in the city, but alarmingly fun times can also be had outside city limits at popular suburban hangs like Hala Kahiki and Chef Shangri-La.
A bookstore may not sound like the most exciting date in the world, but places like Lincoln Park’s Kibbitznest are tailor-made for winter.
Fortunately, comedy shows tend to be pretty cheap dates.
Options for winter ice skating used to be fairly limited in Chicago, but these days in addition to Millennium Park you can now lace up at outdoor venues like Maggie Daley Park and The Park at Wrigley, not to mention local parks like Wentworth Park where you can try (and fail) to reenact the closing scene from Drinking at a fireplace bar is a rite of passage during Chicago winter, but not all fireplace bars are created equal.
Take your date to the next level with either a day trip to a local ski “resort” like Villa Olivia or the newly renovated Wilmot Mountain, or test your relationship with an overnight trip a bit further afield somewhere like Devil’s Head or Cascade Mountain.
We recommend Boyne Mountain for some of the best skiing in the area.
Since knowing that the mural on Damen in Wicker Park opens up to Violet Hour is no longer considered insider information, Booze Box is a sexy bet, The Office is uber-swank, and East Room is not technically secret but does lack proper signage.
As tempting as it may be to host a date in your apartment in the comforts of your (super-sexy) Cubs Snuggie, the dating world doesn’t go on hold just because the thermometers dip below zero.
The good news is there are plenty of hot dates to be had in the cold of Chicago winter.
If you’re looking to get a bit more rowdy, Brew & View is never a bad idea, while a fancy dine-in movie theater like AMC Dine-In Block 37 is the ultimate low-pressure, two birds/one stone lazy afternoon out. Take in the fresh air on a winter stroll along the 2.7-mile elevated path from Bucktown to Humboldt Park (with plenty of bars and restaurants nearby), or hold hands as you gaze out into a frozen yet eerily beautiful and quietly calm Lake Michigan along the 18-mile Lakefront Trail.
In honor of the Winter Olympics, get your Canadian bowling fix at the rooftop curling rink at The Gwen (/person with a free cocktail) or get really involved in the old man winter sport of kings at the Chicago Curling Club (yes, this exists -- but it's more expensive for serious lessons).