How to Love Chicago Winters in 5 Easy Steps

Boogie Woogie Winter

My life is a love letter to the great city of Chicago. I grew up south, went to college north, flew 4000 miles east, then landed west. When I got back, I knew I’d never leave Lake Michigan, XRT, and bar banter again–taxes and all. So how do you stay in love with Chicago when it’s blizzarding on Halloween?

There are secrets to successful enjoyment of Chicago’s brutal winters. It’s not just the frozen earth, wild wind, and snow up your nose. It’s the 5 p.m. blackness, the detachment from neighbors, and the anxiety of bracing for adversity.

Bear up, Chicagoans! Through these elements, we developed a reputation for preparation and planning. Companies around the country welcome Chicago employees for knowing how to get things done despite the elements. Sure, we can be boozing, swearing, brutal couch potatoes. But we connect in crazy conditions. And we’re fun.

Here is my recipe for How to Love Chicago Winters in 5 Easy steps as you fall forward.

  1. Commit. Make a promise to schedule dates with the great city of Chicago through April 2020.
  2. Seek. Time Out Chicago Event Calendar. Red Tricycle Awesome List. Thrillist list for compassionate souls.
  3. Sketch. Create a wish list of all the concerts, classes, events, and visits you found. Think about things you always wanted to try, do or learn.
  4. Balance. Pair physically active events with dark weekday nights. Ruthlessly delete anything you can’t afford, and replace it with something that won’t drain your emotional or financial bank balance.
  5. Schedule. Make your joyful plan official and book it! Your winter experiences are warm gifts from Chicago with love.


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