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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.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.
Or, if you’re feeling more adventurous, sign up for their City of the Month Club and receive a new city box near the first of each month. There are few more loving gestures than showing you actually HAVE been listening all these years.
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.
So bundle up and get cozy with these can’t-miss winter date ideas.
Second City is, of course, the granddaddy of comedy-themed date nights, but good times can also be had for fewer dollars (and fewer people from Iowa) at indie comedy venues like the Cornservatory or regular stand-up nights like Timothy O’Toole’s “Comedians You Should Know” (see full list here).