7 Reasons Chicago is Best in Winter

We can all agree Chicago is an incessant blast in the Spring, Summer, and Fall.  But what about the Winter time?  A lot of people make the greenhorn mistake of writing off America’s greatest city when temperatures dip below freezing, and everything is encased in an opaque layer of snow and ice.  However, Winter is actually the best time to be in the Windy City.  Here’s why:

(1) You Can Wear Anything

Winter Clothes

As a capable, functioning, adult, particularly an employed one, we’re forced to adhere to the constricting common laws of civility and dress ourselves in a presentable manner.  Not just occasionally, but EVERY DAY.  It’s oppressive.  Every day brings forth the herculean task of bathing, grooming, and outfitting to the weighty standards imposed by society.  If you want to go to work without showering, or combing your hair, and wearing snow pants, a gravy-stained Snuggie, and unlaced house shoes, you’re labeled a “slob” or a “pigsty” or a “homeless person.”  It’s downright unjust.

Fortunately, all those fascist personal-appearance rules go out the window when Winter blows into town.  There’s a sartorial hall pass you get when the temperature drops below 15˚F (and correspondingly above 95˚F).  It’s a fact.  Even the most fashionable maven of clothes-wearing gives up and starts layering jackets on top of scarfs on top of coats on top of shawls.  Just ask Anna Wintour.

December, January, February, and if we’re lucky March, are the months we get to grow out a big Civil War general beard, adorn five polar fleece jackets at once, and never take off our Blackhawks pom-pom beanie.


(2) Romance

Wicker Park

There’s a lot of talk about the Summer Fling, but a romantic relationship Chicagoans get to enjoy is the Winter Warmer.  This happens when frigidity sets in, heating bills go through the roof, snow inhibits travel, and Netflix subscriptions swell.  Temperatures are at an annual low, yet libidos shoulder on.

When weather’s permitting, it’s easy to go out to bars, clubs, volley ball courts, block parties, and farmers’ markets (trust us, it’s a goldmine) to pick up unattached people like ourselves.  But come December, it’s a whole different ball game.  Inventory plunges and it becomes a seller’s market.  Much like how lions of the Serengeti have their choice of the animal kingdom to devour, meanwhile the arctic wolves of Melville Island have to resort to snow beetles and tree bark because they never know when their next meal will come.

So if you’re not “traditionally” attractive and saddled with off-putting personality quirks, this is your opportunity to date up.  In the Winter, courtship in Chicago often feels like if you went to the grocery store and found a bottle of 18-year old Glenfiddich on the top shelf with a misplaced decimal price tag and you took it to the check-out counter and the cashier actually rings it up for $1.19 and as they’re handing you the bottle in the paper bag, you want to tell them they’re making a huge mistake by selling you this grossly underpriced Scotch that’s actually worth 100-times as much and should rightfully be out of your price-range, but you bite your tongue and take it home with you eventhough, deep down, you feel you’ve committed a cosmic injustice on some level.  It’s like that.

Which leads into the next reason Chicago is awesome in the Winter:


(3) Drinking

Drunk Chicagoan

Winter’s good for drinking for several reasons.  For one, it gets dark earlier, so happy hour, relatively speaking, is like 2pm.

Secondly, when it gets frosty, way fewer people are going out to get toasted.  As a result, most bars are virtually uninhabited, especially when football season ends.  So when you walk into a Chicago bar in Winter, you’re basically Jack Nicholson in the Gold Room scene from The Shining.  Where in the high season, you have to do jumping jacks in front of the bar to get a can of Hamm’s, in the icy low season, bartenders are so happy someone actually shouldered the storm to come to their establishment, they can’t pour you a free shot of whatever you want fast enough.

Third, it’s a frozen tundra outside.  What else are you going to do?

Fourth, if you get overserved, and have trouble walking back home, don’t sweat.  If you lose your balance and fall over, there’ll be a cushy snowbank to break your fall.


(4) Eating

Obama Eating

Winter’s a good time to eat all the garbage that you’ve been denying yourself for the last nine months: the Chorizo Deviled Eggs at Bangers & Lace; the Double Layered Beer Cheese Baked Nachos at Fatpour; the Oreo Cookie flapjacks at the Bongo Room; those gelato doughnut sandwiches at Glazed & Infused.  All things we’ve been dreaming about all year long and will be stuffing into our ever widening faces this Winter with reckless abandon before proceeding to wash it all down with a growler of Roland the Headless Oatmeal Stout from Piece.

Yes, it’ll cause us to go up a few pant sizes, but remember what we talked about in Reason #1?  You’re basically wearing a sleeping bag with sleeves when you go out.  No one’s gonna see your flabby saddle bags of flesh under all that Winter garb.  Just start doing some burpies the day after the day after the St. Patrick’s Day Parade and you’ll be fine by the time swimsuit season rolls back around.


(5) Solidarity with Fellow Human Beings

Bears Embrace

Remember living through World War II?  We don’t either, but our sanctimonious grandparents never shut up about it.  Any time we’re talking to Na-na and say something like, “God, they ran out of cherry peppers at Craft Pizza, so we had to order pizza with just regular mixed sweet peppers.”  They always bring up their experience as young people suffering under the government imposed rationing of household goods.

While admittedly boring when being recounted by your elderly grandparent, the sentiment of their griping still rings true.  Collective suffering unites people and gives the individual a little bit of grit.  Just like people, as a whole, relinquishing sugar and pitching wedges to fight the Nazis during the Second World War, the cold weather forces you to relinquish patio seating and easily parking your car.  Winter may cause suffering, but everyone’s suffering together.


(6) Sleeping

Mouse sleep

The worst thing about Summer is how debilitating it is to your R.E.M. cycle.  First of all, it’s light for about 20-hour out of the day.  Second, humidity and high temperatures make your bed feel like the inside of a dog’s mouth.  Third, the entire animal species conspires against you by waking up at the crack of dawn and joining together in an unholy choir to chant their respective mating calls at full volume.

Contrast that with Winter where it’s dark from 4pm to 10am, it’s cool enough that you can sleep in your clothes, under your covers, with an extra blanket, and every creature from bear to butterflies is under a snowbank in a silent perpetual state of metabolic dormancy.

People like to throw around the expression, “you can sleep when you’re dead,” but in Chicago, you don’t really need to wait that long.


(7) Discounted Rooms at Holiday Jones


Have you looked at how cheap rooms are at Holiday Jones?  The rates have been slashed up worse than your favorite pair of jorts.  Now’s your opportunity to take advantage of a great room at a low price before our incompetent revenue manager wakes up.