The Ultimate Guide to Winter in Downtown Chicago

If there’s one thing Chicagoans are very good at, it’s talking about the weather. And, for good reason – we get it all! Sunshine, rain, sleet, snow…heck, I’ve even seen ice fall from the sky. The temperature swings are wild too. Come April, it’s not uncommon to wear a parka, raincoat, and flip-flops all in the same week. 

We live for springtime, play hard all summer long and know how to get cozy in the fall. And then, there’s winter. Yes, it’s cold. And yes, it’s long. But it doesn’t deserve a bad rap.  

Whether you were born and raised here, or just moved to the city (welcome!), I challenge you to join me as we reframe what it means to get through winter when you live in Chicago. Let’s not just slog through the season, let’s learn to love it. 

Step One: Prepare to Survive the Winter

First things first, it’s hard to love winter if you’re not prepared for it. And I’m not talking mentally (we’ll get to that too) – I mean, are you physically prepared to make it through winter comfortably? If you’re a transplant from a warmer climate, listen up! 

A woman walks through downtown Chicago with snow falling around her
Having a great winter wardrobe, including a coat, boots, and cold-weather accessories, will keep you warm even when the snow is flying!

The Winter Gear You’ll Need When You Live in Chicago

Sometime in early fall, we’ll have a day or two when the air will turn unseasonably crisp –  a preview of what’s to come a few weeks down the road. This is your signal to take inventory of your winter wardrobe. If you’re new to the Midwest, grab your credit card; it’s time to go shopping! 

You’ll want to have winter jackets that cover a variety of temps and precipitation. The average winter temperature in Chicago is around 20°F, but it’s common to have uncommonly warmer days (think 45°F) or uber cold days (yes, below zero). In my opinion, every Chicagoan really needs just two different types of winter jackets: 

  1. A cozy fleece or light puffer coat, for mild winter days and even light dustings of snow. 
  1. A warm winter coat, such as a parker or down-filled puffer jacket, that’s able to withstand cold temperatures, wind, and snow.

But, if you live in Chicago long enough, that two-coat wardrobe will quickly multiply. I’m jacket-obsessed and have no fewer than a dozen winter coats. My best performers are from L.L. Bean and Patagonia, but I love my fun cheap-and-chic puffers from H&M and Target. 

Having a wardrobe of different jacket options makes winter more fun! If you’re an inexperienced winter coat buyer, here’s my best advice on what details to look for: 

  • Winter Coat Filling: Most winter jackets are either filled with down or synthetic fill. Down is extra warm and lightweight, making it a great choice for travelers. Synthetic fill is cheaper, and still provides great warmth but does tend to be bulkier. 
  • Hood or High Collar: Walk down Michigan Avenue in a blizzard, and your neck, chin, and ears will thank you. 
  • Adjustable Cuffs: Being able to tighten your jacket cuffs snuggly around your gloves will keep you extra warm and dry. 
  • Water-Reistance: If you’ve ever experienced a snowfall when the temp is hovering near freezing, you know why this one is key. Heavy, wet snowfalls are common in Chicago, and the moment that snow hits your warm body, it melts. A waterproof jacket is a lifesaver. 
  • Fleece-Lined Everything: Choose a winter coat with a fleece-lined collar, cuffs, and pockets. Your bare skin (especially your wind-chapped cheeks), will be so much happier when protected by a soft layer. 
  • Jacket Length: The longer the jacket, the warmer you’ll be!

Now that you’re set with a great winter coat, stock up on fun winter accessories like: 

  • Mittens and Gloves: Invest in a few pairs of mittens and gloves. Splurge on a leather pair of Hestra mittens or grab a more affordable pair of classic-turned-trendy Carhartts
  • Hat: You won’t always need a hat, but on extra cold days, you’ll be happy you have one. A warm ear band will do too! 
  • Scarf: The bigger, the better, but avoid bulky knitted scarves. Instead, invest in a thin cashmere blend that double wraps around your neck and tucks neatly into your coat.

Lastly, don’t forget about your feet. I don’t know about you, but once my feet are cold, it’s all over for me. I’m an expert in keeping feet toasty warm all winter long. Make sure you’re ready with: 

  • Winter Socks: No, you don’t need to buy ridiculously thick wool socks, but consider investing in some nice Merino wool socks from a quality brand like SmartWool or Bombas. 
  • Boots: A good pair of insulated duck boots are your best bet for getting you through Chicago winters! Shop for a pair with a waterproof and insulated sole. Pro tip: get a pair with a zipper up the ankle to make taking them on and off a breeze. 
  • Slippers: Every midwesterner has a favorite pair of slippers. More than just fashionable, a good pair of slippers are a must when surviving winter in Chicago. Get a popular pair of sheepskin Uggs or choose one of Wirecutter’s picks for the best slippers this year

Outfit Your Apartment for Winter Too

Now that you’re prepared to stay warm and cozy, let’s make sure your apartment is outfitted for winter too. Whether you’re renting a luxury apartment in the Gold Coast or live in one of the newest apartments in South Loop, you’ll want to get a few items to get your place winter-ready: 

  1. Get a Doormat (or Two): Luckily, you won’t be entering your front door right from the winter elements, but your boots will still need a place to land. A microfiber doormat will trap water, snow, and slush, keeping your entryway clean and dry. 
  2. Hang Up Some Coat Hooks: You’ll need a place to stash all your new coats! If you’re short on space, hang up a few hooks by your front door to catch your coat and scarf. 
  3. Run a Humidifier: Forget the snow, dry air is my biggest winter annoyance. Running a small humidifier in your apartment does wonders for your skin and sinuses. 

Step Two: Learn How to Thrive in the Winter

You’re all set to survive winter in Chicago; now let’s talk about learning to enjoy it! 

Live in Chicago, and you get the great pleasure of experiencing all four seasons. This is actually my favorite thing about living here. And, I don’t hate on winter. In fact, I kinda love it. 

Enjoy Guilt-Free Nesting

I go hard all spring, summer, and fall – Cubs games, bar crawls, outdoor concerts, biking, running, and kayaking. If there’s a way to enjoy the gorgeous weather, I’m there. Then come November, I’m ready to embrace my inner homebody. 

On the first snowfall each year, I kick off my winter nesting season, tackling all the things that I’ve put off for months. And yes, I do it all while reacquainting myself with my winter BFFs –  Netflix, Hulu, and HBO Max. Throw on your favorite sweats and slippers, find a good binge-watch, and tackle these tasks: 

  • Clean out your camera roll. 
  • Go through your closet and pull out donations.
  • Sort through kitchen cabinets and toss anything that’s expired. 
  • Review subscriptions and cancel anything you don’t use. 
  • Plan and book summer vacations! 
  • Clean the oven, refrigerator, and freezer. 
  • Create digital photo books of the prior year. 

If you’re digging the homebody vibe, but have had enough organization, dive into your kitchen and discover your inner chef: 

  • Become a sourdough connoisseur. 
  • Host a monthly progressive dinner with neighbors in your apartment building. 
  • Master the art of the perfect cheesecake. 
  • Learn how to spatchcock a chicken. 
  • Take an online mixology class

Explore Chicago’s Best Indoor Attractions

If you’re bored in Chicago, you’re doing Chicago wrong. The best part about living downtown is that there’s always something to do, and there are awesome indoor entertainment options to keep you busy in the winter. 

When the winter wind is biting, I like to grab some friends, channel my inner child, and have a little fun! These are the best indoor fun and games in Chicago: 

  • Conquer an escape room at South Loop’s Fox in a Box.
  • Keep your game from getting rusty at Play18 indoor golf course. 
  • Head to Evanston and catch a Northwestern basketball game.  
  • Host a ping pong tournament at Spin.
  • Brush up on your bowling game at 10pin.  
  • Discover the hilarity of Whirlyball
  • Skydive without fear at iFly in Lincoln Park. 
  • Give curling a try on The Gwen & Rooftop Terrace
  • Shuffleboard isn’t just for cruise ships. Get your shuffle on at Royal Palms

If you’re looking for something a bit more sophisticated, spend an afternoon wandering through one of Chicago’s best museums: 

The exterior of the Chicago Museum of Contemporary Art in downtown Chicago
The Chicago Museum of Contemporary Art is a great spot to spend a winter day. Image courtesy: Josh Wilburne.

Discover the Best Outdoor Winter Activities

We all know getting outside is good for us, no matter the season. Thriving in the winter means getting out and filling your lungs with crisp, cold air. 

There are so many fun outdoor activities to do in Chicago in the winter. Ice skating downtown is a favorite, and is especially perfect for a date night or a day of family adventuring. The best spots to ice skate in downtown Chicago are Maggie Daley Park or McCormick Tribune Ice Rink in Millennium Park.

If you’ve never been sledding before, what are you waiting for? Sledding is a right of passage for every midwestern kid, but you’re never too old to check it off your bucket list! Cricket Hill, along the Lake Michigan shoreline in Uptown, is the best sledding hill in downtown Chicago. Of course, sledding does come with some risks. If you’d like to avoid a visit to the orthopedist this winter, try snowshoeing instead. Head out to Northerly Island Park for an urban snowshoe adventure!  

Drink and Dine Outside (Yes, in the Winter!)

You might think there’s nothing quite as wonderful as lounging on a downtown patio and sipping a cold beer on a summer day. But, have you ever dined under a winter sky? We don’t let a little winter chill get in the way of dining and drinking al fresco. 

These are my 5 picks for the best places to eat and drink outside in Chicago, all winter long: 

  1. The Winter Wonderland at the Godfrey Hotel 
  2. Check out Fireside’s retractable roof patio, complete with a fireplace 
  3. Get rowdy at the Rambler’s beer garden
  4. District Brew Yard’s patio keeps it cozy with fire pits and heaters
  5. PB&J in West Loop has an ice bar, complete with an ice drink luge 

Step Three: Feel Alive and Embrace Winter

This is the ultimate goal when you live in Chicago. Fully embracing winter and even looking forward to it! Trust me, life is better when you shift your mindset and embrace the beauty of winter.

Develop Daily Winter Routines

I have friends who naturally love winter, but for me, it didn’t come so easily. Yes, I learned to seek out winter fun and even look forward to a good snowstorm. But I didn’t hit peak winter form until I intentionally set winter routines. 

First – take daily walks, no matter the weather. Trust me, once you make a habit out of it, you’ll crave them. I make a point to get outside every day, with no excuses. Of course, it’s hard to say no to my labradoodle. We hit up Chicago’s best dog parks, like Lakeshore East and 569 Bark Park, all winter long.

Another daily habit I crave all winter is sunbathing. If you’re scratching your head, stick with me. Just 15 minutes of daily Vitamin D can seriously be life-changing – especially in the winter. We all know sunshine is good for your mood, but it can also: 

  • Lower blood pressure
  • Boost immunity
  • Promote eye and bone health
  • Help you get better sleep

The best time to score winter sunshine is in the morning. Combine your daily sun dose and winter walk, or catch some rays on your balcony. If a cloudy day ruins your fun, a winter therapy light does the trick too! 

Treat Yourself to At-Home Winter Luxuries

When the weather turns chilly, you’ve got to treat yo-self. When your luxury apartment in Chicago has amenities that cater to keeping you happy in the winter, embracing winter comes naturally. 

My winter happy place is in the steam room in my apartment building. From November to March, you’ll find me sweating out my stress (and warming up my core) every chance I get. 

Apartments in Chicago have totally stepped up their amenity game. These are my favorite apartment amenities that you’ll use all winter long: 

  • Outdoor fire pits
  • Indoor pool
  • Steam rooms and saunas 
  • Game rooms with arcade games and billiards
  • Bowling alley
  • Atrium and garden spaces 
  • Meditation room
The spa at The Paragon apartments in downtown Chicago
The spa at Paragon apartments in Chicago’s South Loop will be your favorite winter hangout. 

Find Peak Coziness With a Hygge Mindset

To learn how to really do winter right, dive into learning and emulating Scandinavian culture and values. Norway to Sweden to Finland – they all land on the list of the happiest countries in the world, despite their harsh winters. Why? Part of the reason is that they’re experts at thriving in winter. 

Have you heard of hygge (pronounced hoo-ga)? It’s the art of embracing coziness and contentment. And really, what else could you ask for in the winter? Hygge is all about slowing down, creating a restful environment, and enjoying life’s simple pleasures – a perfectly ripe pear, warm towels right out of the dryer, and a good book. Hygge is a year-round lifestyle, but in winter, the cozy factor really shines. 

So, how do you channel your inner hygge? Start at home. During harsh Nordic winters, homes across Scandinavia are aglow in the dark of the season. Yes, literally glowing! The goal is to create a sense of warmth, so around daylight savings time, switch to warm-toned lightbulbs. Soft white is great for ceiling lights, but adding amber lights to lamps and wall sconces really amps up the warmth. Next, start an evening ritual. Light candles at dusk, dim the lights, and embrace the darkness of winter. 

Once you create some mood lighting, turn to your furnishings. Swap out your summer bedding for flannel sheets and a fluffy duvet. Make an Ikea run and buy blankets by the cartful. Scatter them everywhere! I even like to use thin plaid throws as tablecloths. Add velvet throw pillows, heavy drapery, and fluffy rugs to your living spaces. Once you’ve created your cozy oasis, you just may find yourself looking forward to winter. 

Catch a Flight and Get Away

And finally, make an escape! It’s much easier to really embrace winter when you break it up with a getaway or two. 

Here in Chicago, we don’t wait for spring break to get away. I love to kick off the New Year with a warm-weather getaway, even if it’s just a long weekend. An escape to a Florida beach or southern California will leave you rejuvenated and sun-kissed! 

If you can take a longer trip, schedule it in February when even the most pro-winter Midwesterners can begin to feel a touch weary. A margarita on a Mexican beach has never tasted better. And my winter-loving self actually loves heading to another winter destination. If you’ve never snowboarded in Lake Tahoe, take the leap! 

The Verdict: Winter is Actually…Fun!

Feeling ready to take on winter in Chicago? I hope so! Remember, step one is survival, step two is thriving, despite the weather, and step three is embracing the season for everything it is. 

Find joy in winter and live your best life in Chicago!