Winter Wanderland

The Best Things To Do In Chicago This Winter

Our neighborhood in Chicago is a vibrant scene year-round, but few locales capture the look and spirit of winter than Andersonville and the surrounding districts. Fallen leaves clear your view of the remarkable architecture and the walkable streets offer endless encounters. Immerse yourself in the red brick and white snow of Chicago in winter––wherever you wander, an unexpected experience awaits.


The Chicago Sketch Comedy Festival

Laugh away the cold at the 17th annual Chicago Sketch Comedy Festival, held January 11th - 13th, 18th - 20th at Stage 773, just ten minutes south of the Guesthouse Hotel. Packed with stars and talent, this is the largest sketch comedy festival in the country, and it's a can't miss event for any fan of comedy.


Lincoln Park ZooLights

Held from January 1st - 7th, head to the world class Lincoln Park Zoo for a trail of lights, hot drinks, ice sculpting demonstrations and, of course, lots and lots of animals, including Siku, our famous 1,000-lb polar bear and resident of the Walter Family Arctic Tundra. The first 1,000 people in attendance each night receive special glasses to view the lights with. Just a quick 13 minutes from The Guesthouse Hotel, this is a perfect event to enjoy this winter.


Visit Historic Carl Street Studios

Once a 19th Century mansion, Carl Street Studios is most famous for being a popular artists' enclave in Chicago in the early 20th Century. In historic Old Town, locals and tourists alike consider the building (as well as the neighborhood in general) a work of art in and of itself.


Warm Up With Some Pizza At Spacca Napoli

Just five minutes from the Guesthouse Hotel, Spacca Napoli was named by Thrillist as one of Chicago's best pizza joints. (They called Spacca Napoli’s pizzas "revered.") These Neapolitan style pies will definitely warm you up on a chilly winter day in Chicago.


Winter Brew 2018

Presented by the Lincoln Square Ravenswood Chamber of Commerce on Saturday, January 27th, check out this “indoor street festival” that features the best beers from Chicago’s thriving microbrewery scene. Dozens of local microbrews will be showcased at the festival, including special limited releases. It’s the perfect event for any beer lover.


Broadway Classic Hamilton Is In Chicago!

Come see the instant Broadway classic the whole country can’t stop talking about! Playing now through April at the CIBC theater, “Hamilton,” the Tony Award winning story of American Founding Father Alexander Hamilton, is a must-see for any theater fan.


Cozy Up Next To The Fireplace At The Guesthouse Hotel

Okay okay, this may be cheating, but we’ve made our peace with that. Not every vacation has to involve you running all over town. We think booking a stay-cation in a different city is a vastly underrated move. And there’s no better place to do that than the Guesthouse Hotel. We’re a converted condo building, so all of our rooms are a home away from home. When the Windy City’s winter winds are at their coldest, we don’t think there’s anywhere better to be than at home at Guesthouse.