9 Brutally Honest Tips to Surviving a Chicago Winter, According to Locals

First winter in Chicago? Congratulations!

You’ve probably heard some horror stories.

But here’s the truth: Chicago winter isn’t about survival.

It’s about strategy.

I’ve spent hours combing through tips from real Chicago locals – the people who’ve lived through 30+ winters here and still choose to stay.

These are the real, no-BS tips that’ll get you through your first winter without either freezing to death or maxing out your credit card.

Let’s get into it.

Tip #1: Adjust Your Mental Calendar

Chicago winter isn’t just cold.

It’s long.

One local puts it perfectly:

“I think the thing you aren’t prepared for when you’re from the south is how long winter is. We’re still in it in March. We’re still in it in April.”

Think about that.

April—the month that should mean spring—is often described by locals as “the worst month of the year” because it’s still “cold, gray, windy, and gross.”

The fix?

Adjust your mental calendar right now.

Winter doesn’t end in February.

It ends in May.

Set that expectation and you won’t spend March spiraling into despair.

Tip #2: Layer Ruthlessly, But Smartly

If you take away one shopping tip from this entire article, let it be this: Uniqlo Heattech.

Multiple locals call it “god tier” winter gear.

These are warm base layers you wear under your regular clothes—pants, sweaters, everything.

There’s no need to spend $800 on a coat when you can spend $50 on base layers that make all your clothes warmer.

Here’s the layering formula that works:

Base layers like Uniqlo Heattech thermals under fleece or wool, topped with a hoodie or sweater.

One local says they “live in their heattech lined pants once the snow comes.”

Another points out you can even get Heattech dress socks for work.

But here’s the crucial part:

Avoid cotton at all costs. It traps moisture and chills you to the bone.

Pro tip: Tuck your undershirt into your pants to seal in body heat. Then when you’re nice and warm, “open it back up like a vent.”

Tip #3: The “Sleeping Bag Coat” Strategy (Yes, Really)

Let’s talk coats.

The most upvoted advice in the thread?

“A coat that’s basically a sleeping bag.”

Locals specifically recommend Eddie Bauer parkas that cover your butt—and there’s a reason for that.

Butt coverage “can make a noticeable quality of life difference in terms of preventing cold wind up the back or for when you need to sit down outside.”

You don’t need arctic expedition gear.

You don’t need to drop $1,000 on a Canada Goose to prove you can afford it.

What you need is “1 good cold weather coat that covers your butt” in the $150-$250 range that’ll last a decade.

Skip cheap parkas and invest in a thigh-length down or synthetic puffer from Columbia or Lands’ End with a hood and reflective lining to bounce back heat. For blizzards, that “sleeping bag” style from Eddie Bauer is a game-changer.

And if you’re on a budget? Thrift spots like Buffalo Exchange or Village Thrift make it affordable.

Pro tip from locals: Hit the Eddie Bauer outlet in Morton Grove or Skokie.

Tip #4: Your Cute Shoes Are Going to Get You Killed

I’m not being dramatic.

Many Chicago locals say that the worst thing about winter isn’t really the cold, it’s the super slippery ice on the sidewalks that comes from repeated melting and refreezing.

Translation? Black ice is everywhere, and it doesn’t care about your fashion choices. Wet sidewalks are liars—always assume black ice.

Bottom line: You need waterproof boots with actual tread. Locals recommend “tall snow boots that zip because you’ll be walking in fairly deep snow more than you think.”

And here’s what you absolutely should NOT do:

Don’t wear Dr. Martens as winter boots.

As one local warns, “DR MARTENS ARE NOT A WINTER BOOT. You will suffer for fashion.”

Instead? Opt for tall, insulated styles like Sorel or Eddie Bauer. Some locals even swear by lightweight Lugz hiking boots for everyday traction without the bulk.

Pair with thick wool socks to keep feet dry and toasty. Locals are evangelical about wool socks: “Smartwool socks will change your life in the cold months. Any merino wool, really. It’s warm, moisture wicking, and anti-microbial.”

The investment? About $100 for a week’s worth of quality wool socks. Brands like Smartwool, Darn Tough (with lifetime warranty), or even Costco’s house brand all get rave reviews.

Tip #5: Traction Hacks for the Ice Apocalypse

Here’s the secret weapon most newcomers don’t know about: traction aids.

Some locals swear by YakTrax, microspikes, or Snowtrax from Costco or REI for extra traction.

One Chicagoan’s advice when you inevitably hit an ice patch? “Walk like a geriatric penguin.” Bend those knees low and live to see another day.

Tip #6: Mittens Over Gloves, Every Time

Here’s the heat retention secret: Fingers together mean more warmth.

Line your mittens with fleece or wool.

Add a merino neck gaiter for windproofing your face—locals specifically recommend this addition to your arsenal.

Don’t forget a hat or fur-lined beanie; ears are heat thieves.

The good news? You can cheap out on these items.

Mittens, hats, scarves, or ear muffs are pretty much all the same and can be treated as semi-consumable instead of a long term investment.

Synthetics are fine. Use whatever. Just protect your neck and digits and ears when you need to.

Tip #7: Prep Your Ride for the Freeze (The Car Survival Kit)

If you drive in Chicago, listen up.

First snow? Find an empty parking lot and “learn how your car handles in slippery conditions.”

Even if you have anti-lock brakes. Even if you’ve driven in snow before.

But that’s just the beginning. Here’s your car winter checklist according to locals:

Stock an ice scraper, snow brush, shovel, and washer fluid in your trunk. Keep your gas tank at least half full.

Have good working wiper blades and keep window washer fluid full with non-freezing wash.

Check your tire tread and keep tires properly inflated—tire pressure drops significantly in cold weather.

Pack emergency gear: gloves, jacket, blanket, hand warmers, extra socks.

Winter tires or AWD with limited-slip diffs handle the salt-sprinkled chaos better than anything. And undercoat that undercarriage—road salt is rust’s best friend.

And here’s the thing nobody wants to hear: On polar vortex nights, some locals disconnect their car battery and bring it inside so they’re “not stranded in the morning.”

Is that extreme? Maybe. But is it more extreme than being stranded at 6 AM when it’s -15°F? You decide.

Tip #8: Fight the Darkness with Connections (The Real Killer Isn’t Cold)

Ready for a plot twist?

According to seasoned locals

“the worst part of winter is not the precipitation or cold, it’s the gloom. Week after week after week of gray skies can be pretty depressing.”

Welcome to Seasonal Affective Disorder territory.

The real killer isn’t the cold—it’s the isolation from short days and brutal winds. Schedule book clubs, movie nights, or dinner parties now.

As one local who’s been through it urges, “Stay connected with people when it’s cold and dark.” Hobbies like puzzles or baking keep the cabin fever at bay.

Here’s what separates people who hate Chicago winter from people who tolerate (or even enjoy) it: Attitude.

One local who loves winter puts it perfectly: “Don’t stop doing stuff because the weather, you’re better and stronger than it.”

The worst thing you can do? Hibernate and wait for April. The real challenge is “staying connected with people when it’s cold and dark.”

Tip #8: Vitamin D and Light Therapy to Dodge the Blues

This isn’t weakness. It’s strategy.

Seasonal Affective Disorder hits hard up here.

Here’s what locals actually do about it:

Pop Vitamin D supplements, especially if you have darker skin or don’t consume much dairy.

Snag a SAD lamp for morning glow-ups. Go outside first thing in the morning when there’s actual sunlight. Exercise indoors if you must, but move.

One transplant credits this routine for “not hating life by February.” Another notes, “The cold and snow are often exaggerated in my opinion, but the lack of sunshine is the real challenge of winter.”

And the big one? Plan a trip somewhere warm and sunny between mid-January and early March. Locals recommend the Gulf Coast of Florida for an affordable long weekend.

Tip #9: The Ultimate Excuse to Eat (and Drink) Your Feelings

The cold provides the perfect, guilt-free excuse to embrace Chicago’s greatest assets: comfort food and strong drinks.

Think of it as strategic insulation.

You’re not just eating deep-dish pizza; you’re building a thermal layer. That steaming bowl of ramen from Furious Spoon? It’s preventative medicine. That boozy hot chocolate from Mindy’s? You’re fighting the gloom one sip at a time.

As one wise local put it, “Drink a lot of beer all year round”—and while that might be a year-round strategy for some, a dark, heavy stout from a local brewery just hits different when it’s 10 degrees outside.

This is the season for malört to actually make sense.

Tip #10: Home Hacks

You might think the battle is outside. Cute.

The real war is fought inside your own home against two invisible enemies: the bone-dry air and the soul-sucking drafts.

First, let’s talk about those charming “vintage” windows – they’re about as airtight as a screen door.

Your landlord isn’t going to replace them, so it’s on you. The single best thing you can do is slap that ugly plastic insulation film on them. 

Yes, it looks weird. No, you won’t care when you’re not feeling a phantom breeze in your living room.

Next, prepare for the utility bill. That first ComEd bill in January? It’s a rite of passage. It will hurt. Budget for it now so you’re not eating ramen for all of February (unless it’s from a great ramen spot, of course).

And while we’re on the topic of unpleasant surprises, find your landlord’s emergency number before a polar vortex hits, because frozen pipes are not a DIY situation.

Finally, the secret to true indoor happiness isn’t the thermostat; it’s what’s on your feet. Cold floors will suck the life out of you. A pair of thick wool slippers or down house shoes is non-negotiable. They’re the difference between a miserable evening and feeling like your entire apartment is a cozy, warm cocoon.

Know the Street Smarts: Snow Rules Edition

Life doesn’t stop—clear your sidewalk (or face fines), watch for alternating parking bans during storms, and embrace the “no coat till 40°F” vibe for milder days. It’s all part of the gritty charm.

Here’s the framework that’ll save your sanity.

One local breaks winter into four distinct phases:

Phase 1 (mid-November to Christmas) is mild, “what most people think of as winter.”

Phase 2 (January) brings solid cold in the 20s and 30s.

Phase 3 (late January through mid-February) is “when winter goes into an extra gear that most cities don’t experience”—single digits, polar vortex territory, when “30s feels warm.”

Finally, Phase 4 (mid-February onward) is the thawing phase “where people walk around in shock at what they just survived.”

The takeaway? Don’t break out your heaviest coat in November. As one wise local advises, “get a good coat but do not break it out until you absolutely can’t stand the cold, then wait a few more days. Your body will adjust to the temperature, but it needs to be exposed to it.”

Save your ammunition for the real battle: late January.

The Truth: Chicago Winter Has Been Dramatically Overhyped

Ready for the final revelation?

Multiple locals agree: “Chicago winters, at least the last couple years, have been… mild.”

The city hasn’t had an insane winter for a while.

Yes, there was a polar vortex in 2019 and another cold snap last January.

Yes, there was a major snowstorm in February 2021 where side streets weren’t plowed for days.

But here’s the reality: For the vast majority of winter, temps are between 20-40°F and average annual snowfall is a little over 3 feet without a lot of prolonged accumulation. Periods of extreme cold or blizzard conditions are comparatively rare.

Bottom line: “It’s winter. It’s cold. But you’ll be fine, I promise!”

Summing It All Up

So there you have it.

The real guide to Chicago winter, straight from people who’ve stared down Lake-effect snow squalls and lived to post about it.

You don’t need $2,000 worth of gear. You don’t need to be miserable for six months. You just need good boots, layers, wool socks, and the right mindset.

Mix in some resilience, and you’ll emerge come spring with stories (and maybe a few frostbite scars) that make you feel unbreakable.

Oh, and one more thing: Remember the golden rule—”Rule number 1: don’t give a shit how you look, give a shit how you feel.”

Now get out there. Winter is coming, but you’re ready.

What’s your biggest Chicago winter worry?

Or if you’re a local, what crucial tip did we miss?

Drop it in the comments below.