Making Yourself at Home: What to do in Chicago this Winter

Making Yourself at Home: What to do in Chicago this Winter

  • Bridget Chambers
  • 12/6/21

It is rare that real estate brokers encourage people to stop thinking about their homes… but we know that in the case of winter in Chicago, even the most dedicated homebodies can catch a grueling case of cabin fever.

Whether you’re in the mind-frame to buy, sell, or stay, you know that living in Chicago brings its residents four distinguishable seasons. And depending on your mood, that might be very great news… or downright detestable. Ready or not, Chicagoans, winter is coming. Let’s try to keep you warm…


The Weather Outside is Frightful

December marks the beginning of a seemingly endless succession of freezing days. Whether you’re a winter lover or a sucker for the summer sun, one thing is inarguable: The cold gets OLD.

Chicago may boast some of the most frigid temps in the country, but it also provides myriad places to go and incredible things to do. In fact, if you’re looking for a way to pass the time this winter, you’d be hard-pressed to find a better place than, well, right here.

Outdoor activities can be most manageable in December because the holidays backlight the city with an array of winter happenings. Here’s where to find the very best ones:

Looking for something artistic and unique? Check out Chicago’s Digital ArtontheMART. There, spectators will find the world’s largest permanent digital art projection, where it showcases contemporary artwork across the 2.5-acre river facade of the Mart every evening.

(Audiences can watch the show from the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street!)

If you’re searching for a family-friendly activity – or just enjoy the thrill of outdoor athletics yourself – you need to look no further than your own backyard. You cannot miss the sledding, skiing, and toboggan hills beckoning for a plunge! Consistently kept primed and well-lit, the Cook County Forest Preserve works all winter long to upkeep hills in the Caldwell Woods, Swallow Cliff Wood North, Dan Ryan Woods, and Westchester Woods.

If you prefer a winter backdrop with a “sporty” feel, the south parking lot at Soldier Field boasts a 220-foot-long hill that was created during the stadium's landscaping redesign. Here, families and adventure-seekers alike can race sleds seven days a week. (The Chicago Park District even utilizes snow machines to keep the hill rideable if there is a seasonal respite in snowfall.)

Holiday lights have been a long-lived and treasured tradition in the windy city, and this year is no exception. Feast your eyes on all things twinkling at Lincoln Park Zoo Lights (hot cocoa and cocktails, too!), gaze at the grandest Christmas tree at Millennium Park, or relish in the illumination of the Daley Plaza menorah. (The beloved Hanukkah display is adjacent to the famed Christkindlmarket, a festive German holiday market that sells exceptional treats and gifts.)

When all else fails, treat your town like a tourist would! Shop the Magnificent Mile, enjoy a Broadway in Chicago show, or really brave those cold temperatures – and a possible broken heart – by cheering for the Bears or Blackhawks at their respective stadiums: Soldier Field and the United Center.


But the Fire is So Delightful

As beautiful as the city feels during wintertime, there is nothing quite as comforting as a warm cup of coffee, a cozy fireplace, or dinner inside with friends.  If 2020 kept you home alone, meeting up with friends and family is very likely topping your holiday wish list this year. When it comes to winter in Chicago, the snow can be enjoyed just as easily from the inside looking out. But, where are the best spots?

Make this year even sweeter by getting creative! Reservations in heated igloos are now offered at some of the city’s best restaurants and lounges. (Try Fulton Market’s Aba, or Wicker Park’s Kennedy Rooftop.) Evenings in Chicago are magical all year, but winter adds a flair of fun to dinners out.

On the other hand, daytime indoor activities are abounding within city limits – and many people find themselves indulging and imbibing a bit more during the colder months. Looking for a day date activity or a group outing with some pals? Try cooking classes (The Chopping Block and The Social Table offer them virtually), wine tastings at City Winery, or shop with some intermittent sips at the Habitant Bar at Nordstrom on Grand Avenue.


Since We’ve No Place to Go…

As the final weeks of 2021 approach, it might seem almost impossible that another year has gone by. Winter can feel invigorating, annoying, or altogether overwhelming. But the holiday season can also be a time for creative projects, deep connection, and quiet reflection. This December, perhaps you’ll consider what you want to do, plan, or decide in the next year. Maybe you’ll revel in the rat race of the holidays, or maybe you’ll stay cozy at home. Maybe you’ll commit to sitting at home with a good book (or gossip magazine), or find time for a phone call with a faraway friend. No matter how you choose to spend your cold December, just make sure it suits you in the ways that make the most sense to you.

Winter in Chicago shouldn’t have to come with a warning label. There is lots of warmth to be found, if only we look just a little bit closer.


In the meantime, let it snow! Let it snow!

Let it snow.

Catch us back here bi-weekly as we bring you curated and Chicago-based real estate content (with a life coach’s twist). Next up: Want to make big decisions in 2022 but not sure where to begin? How about here... New Year...New Home? How to Know Whether to Stay or Go


Work With Us

Partners Sophia Klopas and Jason Stratton are a brother and sister team who have been in the Illinois real estate market for over twenty years. Together they offer complementary skill sets and professional expertise that make KlopasStratton truly unique.

Follow Us On Instagram