Warm up to the city's impressive live theater and comedy offerings. The Goodman Theatre, in the Loop, is a solid choice for a play, and the Cadillac Palace Theatre is like a slice of Broadway in Chicago; comedy fans should check out the legendary Second City Chicago Theatre, a career launching pad for John Belushi, Mike Myers and many others.
Savor the city's sporting scene by taking in a Chicago Bulls or Blackhawks contest at the United Center. For something a bit different, head to the Sears Centre in the northern suburb of Hoffman Estates, to see the Chicago Storm of the Major Indoor Soccer League in action.
Winter might seem like an odd time to visit an Italian restaurant named for the beach but Spiaggia, on N. Michigan Avenue, is a deluxe dining experience in every way imaginable. From the sky-high windows overlooking Lake Michigan to a menu showcasing mouthwatering items like handcrafted spaghetti with lobster and wood-roasted Mediterranean sea bass, this is without question one of the finest restaurants in the Midwest.
Film buffs will especially savor taking in a classic flick at the Music Box Theatre on N. Southport Avenue, built in 1929. From ancient wonders like Metropolis to midnight movie standbys like Pink Floyd's The Wall to off-the-wall events like sing-along version of Grease and Xanadu, this is a unique movie Mecca with a creative bent to it.
Spend a snowy day with Pablo Picasso, Henri Matisse, Salvador Dalí, Andy Warhol, Edward Hopper and Grant Wood among many others at the Art Institute of Chicago. A charming restaurant and decent shop add to the attraction, and this is a great place to spend a few hours or more on a cold afternoon.
For an array of holiday shopping options, or a bastion of post-holiday bargains, head to Water Tower Place, a bustling eight-story atrium of tasteful stores, eateries and more. From Abercrombie & Fitch to Brookstone to Sharper Image you'll find more than enough cool stores here to occupy a cold afternoon.
With its fireplace, warm ambience and lively patrons, Bar Thirteen on West Division Street might be the perfect tavern to hunker down in on a snowy evening. Arrive relatively early if you're planning to lounge on one of the comfy couches or find a good spot at the handsome oak bar.