How to Survive Winter in Chicago

Today is the first official day of Spring, but before we look ahead we want to pause to dish about the past 3 months here in the Midwest.

To say it’s been a rough winter in Chicago would be the understatement of the season.  It hasn’t just been rough. It’s been brutal. Picture subzero temperatures, bone-chilling wind chills, thick layers of ice, and heaps of snow and you’ve pretty much summed up the past few months in the Chicagoland area.bridgetCasey-Chicago-WinterBut being 2 positive gals, we’re not here to give you the “poor us” spiel (especially since some east coast places had it waaayyy worse than us!!). Instead, we want to tell you how we survived (& thrived) this winter season.

Here are 5 tips to Survive Winter in Chicago

1. Proper Footwear: We both absolutely love leather boots. Is there a cuter way to dress up jeans than with little booties or knee-highs? We don’t think so! But unless you want salt-stained boots and cold, wet toes…it’s probably a good idea to avoid the cute boots altogether. Instead, we go for more heavy-duty footwear.


Bridget’s Boots

I love these boots because I don’t mind if they get wet and salty! I can easily wipe away the salt stains and these puppies are looking back to normal. I actually got these Sperry Topsider “duck boots” as a b-day gift in October and wore them everywhere this winter. Awesome gift!! I usually paired them with some warm, colorful socks like in this picture and my toes were sure to stay dry and toasty.

Hunter-BootsCasey’s Boots

I (Casey) have worn my Hunter boots just about every single day this season. They’re amazingly durable and are actually quite warm when you wear the liners inside. My Hunters have gotten beat up over the past few months as I’ve worn them on my commute to & from work, but I simply just wash the salt and slush away every week or so, and they look good as new! I’ve also kept a pair of flats at the office so I can change out of my big ol’ boots and not feel so clunky all day long.

2. Warm Jacket: A comfy snow jacket definitely tops our list of winter essentials. Extra credit if it has a hood and goes down past your knees. The only way to battle the cold is with this extra layer of fluff on top of your 2-3 layers of sweaters and clothing. Who cares if it adds an extra 20 lbs on your frame? We’ll be poufy fluffballs every day of the season, as long as we’re warm and toasty inside.

Bridget’s Coat / Casey’s Coat

3. Plenty of Accessories: One of the only “fashionable” things about winter is the ability to mix and match a variety of scarves, hats, headbands, and gloves.  We’ve both collected our fair share of colorful scarves, knit hats, and fuzzy earmuffs. It can be fun to accent our black coats with a pop of color, and those cozy accessories definitely come in handy every single day during winter. You won’t ever catch either of us without these essentials on or tucked inside our bags.

PS. Don’t be too impressed by the Patagonia Coat label. I scored this typically very expensive coat at an outlet store in Maine (while I was on my honeymoon!). I bought a girl’s size instead of a women’s size and saved myself even more money (pretty embarrassing, I know)!! This coat cost me LESS than $100 and is hands-down the WARMEST coat I have ever had!



4. Warm Heads: Okay, maybe that’s not the best way to phrase it..but having covered noggins is a must with this kind of weather. They say heat escapes from the top of your head (is that really true? We’re not sure!), so we follow that logic. You better believe you’ll see us with our hoods up and ears covered when we’re out and about during the winter. Perhaps not the best for our peripheral vision (gotta look left, right, left about 10x before crossing the road!), but our big hoods definitely keep us sane during the coldest days.

bridget5. Cozy Days/Nights Indoors: The best tip to survive Winter in Chicago? STAY INSIDE! Yes, it’s easy to get a little stir crazy indoors all day, but we’ve both tried our best to make the most of these frigid temps and snow days. Turn up the heat, cuddle under a blanket, sip a hot toddy, and enjoy time inside with your loved ones. It won’t always be this terrible outside, so enjoy some down time and relaxation while you can.


We’re not sure what spring will be like here in Chicago, but we’re keeping our fingers crossed that the worst is behind us. Heck, at this point 30 or 40 degree days will feel like bikini weather!

bootSo let’s officially say our goodbyes to winter, as we give spring a great big bear hug!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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