8 Ways to Enjoy Winter in Chilly Chicago


"It's funny how you find you enjoy your life / When you're happy to be alive."

Do you recognize this song lyric? I don't even want to mention the band because it's an embarrassing throwback to my younger years. But it's completely true.

After the Big Panini stole two years of our lives, we dreamed of reclaiming that time by living life to the fullest, which included our big move to Chicagoland. We arrived at the onset of winter, and everyone thought we were crazy. "You moved from California, where it's always sunny with a high of 75, to set up a new life while the season's first snowflakes fell outside? Not the decision I would make."

Every minute of our lives is what we make of it. My decision to be happy and have fun in every season of the year, whether bitter cold or unbearably hot, requires an attitude of gratitude, to God and to the life I've built with Brandon. We have fun because we choose to have fun. It's that simple.

Now, sermon over, please sit back and enjoy 8 ways we chose to embrace our first winter in Chicagoland.


#1: Our first Chicago Bulls basketball game, on Valentine's Day, no less. Bulls won, go Bulls!


Maybe this is the cheap talking, but we were genuinely pleased with our seats up in the nosebleed section. We thought the view was better!


#2: We savored a steaming cup of mulled wine in this 25 year anniversary collectable mug at the Christkindlmarket.

A seasonal favorite, the German market is hosted in two Chicago locations - downtown in Daley Plaza and in Wrigleyville.


We sampled the stuffed Bavarian-style pretzels in flavors like jalapeño and cheesecake, washing them down with tall cups of marshmallow-loaded hot cocoa.


As a way to escape the frosty outdoor conditions, we always take a lap around the Christmas ornaments tent. The glass baubles, all handmade in German, are gorgeous and pricey.


Our sweet Guatemalan neighbors, Nathalie and Blanca, took us under their wing immediately after we arrived in Chicagoland, inviting us to Christmas Eve dinner at their house (Brandon made perogies) and bringing us to Christkindlmarket as our first big trip to the city. Bless these bundled people.


#3: Then they took us to the best Christmas-themed bar in the whole city for a burger and neon-colored drink - Santa Baby Bar in Wrigleyville.


Overwhelmed is a great word for how this bar's decor made us feel, in the best way!

Click here to read my full blog post about Santa Baby Bar and see the mouth-watering, seasonal food and drinks.


#4: Our sweet sister Phoebe came all the way from Oregon to visit us right after Christmas for a rapid 24-hour stay. We took her to The Second City for a holiday Hallmark musical improv show, filled with belly laughs and Christmas-themed stereotypes. We loved it.


#5: My adventurous neighbor, Nathalie, took me to the city for a blowout the day before Valentine's Day. We got dolled up, hair washed and curled, took selfies, then headed to breakfast.


We indulged with these soufflé pancakes at Hanabusa Café across from Millennium Park. I ordered the purple taro sauce and she had the matcha version. Pillowy, delicious!


#7: Located in the heart of the city, the Art Institute displays some of the most famous masterpieces in the world - like American Gothic by Grant Wood and the pointillism wonder A Sunday on La Grande Jatte 1884 by Georges Seurat - along with other ancient and modern works that we found equally impressive.


#8: If all else fails, you run out of Chicago activities to do, and the winter blues start to creep in, there's always one option left - travel!

Chicago O'Hare Airport may be a challenging airport to navigate in a rush, but we are undeniably grateful to live near an international hub that has transported us to countless adventures in the U.S. and around the world, with many more to come.


With the right mindset, winter can be a joyful season. Come visit us in Chicagoland and we'll show you!

Click below to see what else we've done this winter: