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18 outrageous ways Chicagoans prepare for winter

Winter is *always* coming—here's how true Chicagoans confront it.

Written by
Time Out Chicago editors

Like deep dish pizza and corrupt politics, Chicago winters—in all their slushy, frigid misery— have attained a legendary status in city lore. The famously bitter season might inspire fear in out-of-towners, but Midwesterners seem to almost relish the masochistic ritual of preparing for winter. And how could we not? Let's face it: There are limited things to do in Chicago between November and March except stare at Christmas lights, drink, hibernate and complain. We might as well embrace it and starting prepping early. Here are just a few of the ways Chicagoans opt to ring in the winter season.

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1. Start complaining about the weather in early November.

Commiseration is one of the only coping mechanisms we have—and boy, do we love to use it.

2. Invest in a SAD lamp.

And pretend it makes up for the sun setting at 4:30pm.

3. Buy Vitamin D pills in bulk.

Somehow they always seem like they'll be the solution to every wintertime woe.

4. Cut spending in every other area of life to accomodate impending energy bills.

Peoples Gas never fails to hike those nebulous "delivery fees."

5. Rearrange your commute around the Chicago Pedway.

Labyrinthian and dingy as the Pedway may be, we'll take any opportunity to stay inside we can get.

6. Get reacquainted with your go-to food delivery apps.

It's almost like Uber Eats knows you have no self-restraint and a desire to not change out of your sweatpants.

7. Abandon all pretenses of street style.

We're lucky puffers are en vogue right now, but that fashionable pea coat just isn't going to cut it once January rolls around.

8. Blow way too much money on a bougie parka.

Or prepare to cast snide glances at passersby who clearly blew way too much money on a bougie parka.

9. Scrounge up mismatched mittens from last year.

They're hiding somewhere in the recesses of your closet... just keep digging.

10. Talk with friends about how it's "supposed to be a mild winter."

Famous last words.

11. Break out the balaclava.

The face mask-and-balaclava combo is an especially good (and very warm) idea this year.

12. Purchase footwear that could be mistaken for moon boots.

It doesn't matter how bulky they are, as long as it keeps your feet dry and your toes toasty.

13. Retire your razor for the season.

More hair equals more warmth, so it's really just the sensible thing to do.

14. Resign yourself to giving up that outdoor running habit.

Unless you're a masochist and/or planning to splurge for thermal tech gear.

15. Invest in plastic to cover your drafty windows.

And dream about living in an apartment with properly-installed double-paned windows while you wrestle with that roll of double-sided tape.

16. Reminisce about polar vortexes from winters past.

If you survived a -50 degree windchill in January 2019, you can survive anything.

17. Scare your warm weather transplant friends with cold weather horror stories.

Sure, you could set them at ease about their first winter here, but it feels better to watch them squirm. Take that, native Californians!

18. Stock up on booze.

Choose liquor that can be added to a hot beverage for some extra warmth.

The rules of living in Chicago


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