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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.Hubbard Inn offers two fireplace lounges on two floors, while Moody’s Pub is a romantic medieval castle-like favorite. Show off how cool you are with your in-depth knowledge of Chicago’s secret bars.Not only is a place like Brooklyn Boulders the ideal location to scale fake rocks when it’s too cold to tangle with the real thing, it also cultivates a fun scene with a regular slate of events including pizza parties, movie nights, yoga, and more. One of the most awesomely weird spaces in the city, Aloft Loft is located in a 109-year-old Logan Square church and offers a variety of circus performances and classes in everything from aerial arts and trapeze to contortion and clowning.If your relationship can survive a clown class, it can survive anything. No matter where you are in the city, it’s guaranteed to be warmer in the Garfield Park Conservatory, which is brimming with lush plant life year-round.If your ideal date involves demonstrating what a stable genius you are, show off your deep base of useless knowledge at one of the many bar trivia nights around town.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.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.Chicago may not be known as a gambling mecca per se, but the city is surrounded by a variety of casinos that can make for a fun alternative to the standard dinner-and-a-movie routine.
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.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).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 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.
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.