Snuggle at a fireplace bar
Drinking at a fireplace bar is a rite of passage during Chicago winter, but not all fireplace bars are created equal. Hubbard Inn offers two fireplace lounges on two floors, while Moody’s Pub is a romantic medieval castle-like favorite. Get the full rundown here.
Lace up the skates and hit the ice
Options for winter ice skating used to be fairly limited in Chicago, but these days, weather permitting, in addition to Millennium Park you can now lace up at outdoor venues like Maggie Daley Park, not to mention local parks like Wentworth Park where you can try (and fail) to reenact the closing scene from Serendipity. It won't be hard to find free skating on the schedules, but keep in mind you'll have to pay for rentals (or bring your own).
Two words: ski trip
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. This may be a pricier option, but the real question is: can you really handle 10 hours in the car together?
Get on your back on a sledding hill
There may not be massive mountains to navigate in Chicago, but you can still tap your inner child through a variety of sledding hills in and around the city. Some of the best options in the city include the Dan Ryan Woods, Palmisano Park, and Caldwell Woods, while the burbs offer an array of hills like James Park in Evanston and Riverside’s Swan Pond.
Test your mettle on a winter hike
The 606 isn’t just for summertime. Take in the fresh air on a winter stroll along the 2-7-mile elevated path from Bucktown to Humboldt Park, or hold hands as you gaze out into a frozen yet eerily beautiful and quietly calm Lake Michigan along the 18-mile Lakefront Trail.
Get intimate inside the comforts of a drinking dome
Instead of (or in addition to) a winter rooftop bar or hot new restaurant, another solid option to get to know your date while experiencing the magic of winter (without all the cold) is to snuggle up in an outdoor drinking igloo at places like the I|O Godfrey, where you can sip hot drinks like the Jameson- and heat-infused Godfrey Toddy while exploring its “Winter Wonderland” rooftop log cabin.