Your Guide to Surviving Chicago Winter

Chicago has lived through more than one polar vortex (a catchy term for days-long stretches of sub-zero temperatures), but the winter chill still tests residents each time it settles in for months on end. The holiday cheer of November and December makes winter seem charming, but once the gray stretches of January and February unfold, Chicago winter can seem all too grim.

Winter doesn’t truly begin to lose its grip on Chicago until May, and even then, it can linger. Don’t be surprised if heaps of snow cover the ground in what are traditionally considered the months of spring. Prepare yourself for the city’s most infamous season with this practical guide.

Parking and Public Transit

Getting around the city in winter can seem like an extreme sport. If you only have to contend with the cold, bundling up and heading out is manageable. But, when you add in snow and icy roads, getting to and from work and anywhere else you might want to go becomes a greater challenge.

If you drive, owning a single-family house with a garage or a condo with an assigned parking spot goes from a nice perk to the best decision you have ever made (Definitely keep this in mind if you are in the market for a new home). Street parking in winter is complicated by the snow and the time-honored rivalry of parking dibs vs. first-come-first served.

During the winter months, the residential streets of Chicago are peppered with all manner of bric-a-brac (patio furniture to old cardboard boxes) to stake out parking spaces that have been laboriously dug free from the snow. You don’t necessarily have to join the dibs free-for-all to survive winter, but it is best not to remove any of those placeholders—unless you’re willing to risk some run-ins with your neighbors.

If you rely on public transportation, you don’t need to worry about snagging a parking spot, but you will likely need to build a little extra time into your commute to account for delays due to inclement weather.

Braving the Outdoors

Once you have mastered the fine art of winter transportation, you’ll find that the city has enough winter entertainment to tempt you outdoors. Beginning in mid-November, the city hosts the annual Christkindlmarket at Daley Plaza in the Loop and at Gallagher Way in Wrigleyville. The open-air holiday festival is lined with booths selling ornaments, wine, roasted nuts, and more. The bright lights and warmth emanating from the different stalls helps to keep the chill air at bay.

If you are in the mood for some more traditional wintertime fun, you can go ice skating and sledding within the city bounds. The McCormick Tribune Ice Rink at Millennium Park and the Skating Ribbon at Maggie Daley Park, both located in the Loop, are full of laughing skaters during the city’s coldest months.

Snow transforms a sizeable slope at Palmisano Park in Bridgeport into one of the best spots for sledding in the city. Families with kids will brave the wet and the cold to careen down the hill.

For something a little less adrenaline-fueled but just as fun, Lincoln Park Zoo celebrates the holiday season with ZooLights. Come to this Lincoln Park gem with the family or for an adults-only night out.

Indoor Entertainment

While some time outdoors in the Chicago winter can be fun and bracing, you’ll probably need plenty of indoor time to make it through the season. If you are looking to warm up in one of the city’s cozier bars, you’ll have no shortage of options. Gilt Bar in River North pairs a warm, inviting aesthetic with craft cocktails and a menu full of winter comfort food. The space even has a more intimate bar on its lower level, The Library.

Cozy doesn’t necessarily have to mean boozy in Chicago. You can also explore the city’s best spots for hot chocolate and tea. Mindy’s Hot Chocolate in Wicker Park has a full food and bakery menu, as well as several twists on classic hot chocolate. For those who like to brew tea at home, Coffee & Tea Exchange in Lakeview has a wide array of varieties that you can buy by the pound.

Winter is also the perfect time to lose yourself in one of the city’s superlative museums. A love of history will take you to the Field Museum in the South Loop, while a love of technology will take you to the Museum of Science and Industry in Hyde Park.

If you are looking for an excuse to dress up during the winter season, the Theatre District of the Loop is never short on shows, both musicals and plays. Catch a classic Broadway production or the premiere of something brand new.

Winter may be long in Chicago, but with a warm coat and local knowledge, you can survive and even enjoy the season.