SIMON'S TAVERN (Andersonville)
Known to locals as "The Anchor of Andersonville," Simon's harkens back to Andersonville's heyday as a Swedish enclave. Grab one of the couches in the back—in front of the fireplace—and order a glögg, a seasonal mulled-wine that will warm your bones.
So, the fireplace here is near the front, and near the windows, so it's not sure how much warming it will do—but it's a great bar to hunker down in, with its fantastic selection of craft beer and an inventive menu from Chef Cleetus Friedman.
TAKE TO THE ICE
If you're brave enough to brave the cold, then check out these options for some outdoor fun!
MILLENNIUM PARK ICE SKATING RINK (Downtown)
$12 will get you a skate rental and time on the ice at the rink at Chicago's famous Millennium Park—go here for more information.
PARSON'S CHICKEN AND FISH (Logan Square)
This hip fried chicken and fish joint decided to make the best of the winter by turning its large outdoor space (which is usually filled by picnic tables and a ping pong during the summer), into a skate shack. For some ice on ice, after taking off your skates, try one of Parson's' Negroni slushies.
KAISER TIGER (West Loop)
Like Parson's, sausage and beer hot spot Kaiser Tiger has a gorgeous beer garden, but can't use it in the winter. So, they installed two curling rinks in their backyard. Yep, that's right, you can grab a broom and play this oversized version of outdoor, icy shuffleboard. Check out the fine print before hand, however.