Top 10 Wintertime Activities in Chicago

I’m not going to sugarcoat it. Wintertime in Chicago is long, cold, and includes the colorful phrase: “wintry mix.” But we Chicagoans are a hardy bunch and don’t just survive, but thrive in the winter. From holiday festivals to wintertime-only bar and restaurant experiences, winter has become one of the best seasons to be in Chicago! If coming to Booth means you’ll be experiencing Chicago winters for the first time, here’s my list of the top ten activities (in no particular order) to help you thrive during the season.

1. Visit Christkindlmarket

My wife and I at Christkindlmarket

A Chicago favorite since 1996, Christkindlmarket is an open-air traditional holiday market inspired by the traditions of Nuremburg, Germany. Over one million Chicagoans visit every year to kick off the holidays! I have personally gone almost every year since high school to eat traditional German food like curry wurst and potato pancakes, drink warm glühwein and hot chocolate, and shop for unique gifts from vendors from around the world. Perhaps most importantly, I make sure to acquire each year’s souvenir mug to add to my collection.

2. Ice skate downtown

Maggie Daley Park Skating Ribbon

Right in the Loop exists two fantastic ice-skating rinks: Millennium Park McCormick Tribune Ice Rink and Maggie Daley Park Skating Ribbon! With the Chicago skyline and “The Bean” as your backdrop, there’s no better place to get out on the ice with friends or for a romantic winter date (yes, from personal experience). Admission is free and rental skates are only $15 or less depending on the date.

3. Experience ZooLights

Did you know there was a free zoo just north of downtown? Did you know that free zoo puts on a spectacular holiday light show every year? The Lincoln Park Zoo is an amazing Chicago attraction that is especially worth visiting in the winter for their annual ZooLights celebration. Stroll through the zoo to celebrate the holidays with the animals, witness live ice sculpture carving, and marvel at the intricate musical holiday light shows.

4. Attend festive shows and concerts

Joffrey Ballet’s The Nutcracker

Winter is the perfect time to enjoy Chicago’s world-class theatre, film, and performing arts scenes. Theatregoers shouldn’t miss The Nutcracker or A Christmas Carol and should definitely take advantage of Chicago Theatre Week later in the winter. If holiday films are your thing, you’ll love Music Box Theatre’s Annual Christmas Double Feature. And it’s not winter without holiday music! Join the annual Handel’s Messiah Sing-a-long or enjoy the annual holiday shows from Chicago Chorale and Chicago Men’s A Cappella, two groups with deep University of Chicago roots.

5. Ride the CTA Holiday Train & Bus

Each year, the Chicago Transit Authority (our public transportation system), decks out a train and bus with holiday decorations, music, and interactive “magical” experiences. But it’s not just about delivering joy to CTA riders—the Holiday Train & Bus also delivers food baskets to charities around the city. Check out the holiday train schedule here.

6. Escape to tropical oases

Garfield Park Conservatory

You don’t have to fly away to escape the cold and grey of winter. Experience green topical oases right here in Chicago at the Garfield Park Conservatory or the Lincoln Park Conservatory. You may even find me here relaxing on a bench, doing my class readings, enjoying an afternoon in paradise. Want to enjoy the tropics at night? Check out one of Chicago’s many tiki bars like Lost Lake, named Best American Cocktail Bar in 2018.

7. Participate in the Polar Bear Plunge

Jimmy Fallon during Chicago’s Polar Bear Plunge 2014

Dare to dive into Lake Michigan in the middle of January? For over 15 years, thousands of Chicagoans and visitors have done just that (including Mayor Rahm Emanuel, Jimmy Fallon, and Lady Gaga)! But it’s not just for the adrenaline, Chicago’s annual Polar Bear Plunge raises tens of thousands of dollars for charities each year.

8. Warm up with Mindy’s Hot Chocolate

Mindy’s Hot Chocolate is arguably the queen of hot chocolate in Chicago. Get the Mexican hot chocolate, and maybe a dessert while you’re at it. You’ll thank me later.

9. Go sledding next to Soldier Field

Relive your childhood by sledding down the hill next to Solider Field, home of the Chicago Bears. Think sledding is just for kids? Think again with the hill’s 33 ft. vertical drop!

10. Eat and drink at wintertime only experiences

City Winery River Domes

We all know Chicago’s food and drink scene is second to none, and some of the most unique experiences only occur during the winter! Don’t miss Frosty’s Pop Up Bar to get into the holiday spirit! Or if partying with thousands of Santas and elves is your thing, TBOX 12 Bars of Christmas is an annual Wrigleyville holiday pub crawl. Looking for something a little more sophisticated? Enjoy a meal and/or drinks in a real life snowglobe overlooking the city at the IO Godfrey Winter Wonderland or along the Riverwalk at City Winery’s River Domes.

There you have it! You’re now ready to conquer the Chicago winter! Just be careful not to break the unwritten rules of “dibs.”

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