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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.Or, if you prefer your bowling with more weird bumper cars, a winter date to Whirlyball is clearly calling your name.Painting parties paired with wine are the name of the game at uber date-friendly spots like Bottle & Bottega.This may be a pricier option, but the real question is: Can you really handle 10 hours in the car together?
The good news is there are plenty of hot dates to be had in the cold of Chicago winter.
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.
If you can’t seal the deal after this date, something must have gone seriously wrong (let’s hope it wasn’t your art).
Chicago’s burlesque bona fides are not to be questioned, and you can sex up your night out with a visit to one of the city’s many burlesque stomping grounds like Untitled or The Drifter.
With a front room stacked with newspapers and magazines, a bar stocked with everything from Chicago dogs to Irish coffee, and a back game room, a quick stop in from the cold here can quickly turn into three hours gone by in a flash.