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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.
The stylish, recently revamped Logan Theatre is always a solid date choice, but becomes even better in winter thanks to their “Jolly January” late-night movie series.
You can also shoot bows and arrows in Humboldt Park at Archery Bow Range Chicago or chuck axes at the wall at joints like Bad Axe (both are /hour for walk-ins, with cheaper rates for groups and other options too).
There is perhaps no easier winter date than at one of Chicago's fine tiki bars: immediately fun, warm, and cozy, the only way you can screw this up is to start talking politics.
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.
The Globe Pub is the granddaddy on the scene, Reggie’s is a great Monday night spot for sports and music trivia, and Simone’s is a standout choice for Q&A trivia Tuesday nights.
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.
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.