Winter Running in Chicago: A No-BS Guide to Not Freezing Your Ass Off

Look, I’m not going to sugarcoat it (unlike my face, which is definitely coated in frozen condensation right now): winter running in Chicago is brutal. But it’s also kind of magical? Like, in a masochistic, “why do I do this to myself” sort of way.

The thing is, there’s no such thing as bad weather—only bad gear choices. And trust me, I’ve made them all. So let me save you from my mistakes and show you what actually works when the temperature drops below “holy sh*t.”

The Real Talk: Layers Are Your Best Friend

Forget looking cute. Forget matching. When it’s 10 degrees outside and the wind is coming off the lake like it has a personal vendetta against you, fashion is dead. Survival is the aesthetic.

Here’s my actual winter running uniform, tested through too many Chicago winters to count:

Head & Face:

• A buff pulled up to cover my ears and lower face (game changer for keeping your lungs from freezing)
• My trusty black beanie from 7-Eleven (yes, really—cost me like $3 and it’s outlasted every “technical” hat I’ve bought)

Upper Body:

• Thermal long sleeve base layer
• ASICS winter running jacket
• Zip-up hoodie over the jacket (because sometimes you need that extra buffer)
• Below zero? Another jacket goes over all of this. I don’t care if I look like the Michelin Man.

Lower Body:

• Athleta Mt. Rainier winter running tights (these are the MVPs)
• Cheap-ass grey sweatpants over those tights (fashion be damned)

Feet:

• Thick wool socks
• Below zero? Thin pair of socks over the wool ones (counterintuitive but it works—traps warm air)

Hands:

• Thick mittens (not gloves—mittens keep your fingers together and warmer)

The “Am I Overdressed?” Test

Here’s the secret: you should feel slightly cold when you first step outside. If you’re comfortable standing still, you’re overdressed and you’ll be sweating your ass off by mile 2.

The rule of thumb is to dress like it’s 15-20 degrees warmer than it actually is. Your body is about to become a furnace.

Things Nobody Tells You About Winter Running

Your snot will freeze. Accept it. Embrace it. Bring tissues or just… yeah, snot rockets are fair game in winter.

You’ll need to pee more. Something about cold weather makes your body think it needs to empty the tank. Plan your route accordingly.

The first mile is a liar. It’s going to suck. You’re going to question every life choice that led you here. Push through. Mile 2 is usually when things start to feel human again.

Your water will freeze. If you’re doing a long run, tuck your water bottle or bladder inside your layers, or just accept you’re doing this run without hydration.

When to Say “F*ck It” and Hit the Treadmill

Listen, I’m all for toughing it out, but there are limits. Below zero with high winds? Ice everywhere? That’s not being hardcore—that’s being stupid. The treadmill exists for a reason.

Also, if you’re not feeling it mentally, that’s valid too. Winter training is supposed to make you stronger, not miserable.

The Bottom Line

Winter running in Chicago isn’t about being perfect. It’s about showing up, layering up, and getting it done. Some days you’ll feel like a badass arctic explorer. Other days you’ll shuffle along questioning your sanity.

Both are completely fine.

And hey, spring running is going to feel easy as hell after this.

What’s your winter running setup? Drop a comment and let me know what gear saves your ass when it’s freezing out there.