- I took my family from a 95-degree Australian summer to experience Chicago’s 5-degree winter weather.
- Everyone warned us December was a bad time to visit, but smaller crowds and festive activities proved them wrong.
- From ice skating to curling, winter-only activities made our offseason trip unforgettable.
Despite warnings from friends and fellow travelers, we decided to spend a December vacation in Chicago.
Nearly everyone tried to talk us out of it, saying it would be too cold and windy and we should choose a warmer destination. But we had a different goal: experiencing a real American Christmas. In Australia, where we live, December means sweltering heat and late sunsets that make holiday light displays practically invisible until 10 p.m.
Despite the cold weather, it was a memorable experience.
We got an extreme welcome to Chicago winter
Our first day coincided with the city’s coldest temperature of the year — just 5 degrees Fahrenheit. Even Chicago natives shivered and complained about the brutal cold.
Despite the arctic blast, we had scheduled a five-hour walking tour through the Chicago Greeters program, a free service that matches visitors with local volunteers. Bundled in multiple layers, we met our guide, Bill, an energetic local in his 70s who quickly proved that Chicago’s famous winter weather couldn’t dampen the city’s charm.
His local stories, mixed with iconic attractions, made for a great day, and he provided recommendations for the rest of our week.
Winter activities became an unexpected highlight
While our usual Christmas involves seafood and beach trips, growing up watching movies like “Home Alone” gave us a different vision of the holiday season. Chicago delivered that movie-perfect Christmas experience with a magical winter atmosphere we had always dreamed about.
We explored the Lights at Lincoln Park Zoo, wandered through the enchanting Christkindl market, and discovered several festive pop-up Christmas bars in Wrigleyville. As a special treat for our half-Jewish kids, they were thrilled to visit the Hanukkah bar, 8 Crazy Nights.
Although our skating skills left a lot to be desired, the breathtaking cityscape surrounding the Maggie Daley Ice Skating Ribbon more than made up for the spills.
The architecture tours impressed even in winter
One thing I was hesitant to do was an architecture river tour. While the city is famous for its buildings, I worried the cold would make it unbearable. But Bill convinced us to do it.
Though many operators had closed for the season, we found a 90-minute cruise. Surprisingly, despite the wintery conditions, this was a great tour, and even the kids loved it. The moody gray skies made for more dramatic photos.
After dark, the city came alive with a holiday spirit
Being close to Christmas, the city offered endless entertainment options. We went to a high-energy Chicago Bulls game where we were incredibly excited to support fellow Australian Josh Giddey, complete with handwritten signs to cheer him on.
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We also saw the Blue Man Group perform, but the highlight for me was visiting Second City. Having completed some online satire writing courses with them during the COVID lockdown, it felt like a pilgrimage to see a show live. My kids were worried I would jump onstage, but despite my best efforts, this didn’t happen.
Chicago’s winter weather demands comfort food
The frigid temperatures gave us the perfect excuse to indulge in the city’s heartiest dishes. We devoured deep-dish pizza at Giordano’s (which quickly became our favorite), savored authentic Italian beef sandwiches, and relished Chicago-style hot dogs.
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The kids loved tasting the endless selection of decadent hot chocolates while my wife and I warmed ourselves with mulled wine and Tom & Jerry’s, a Midwestern holiday cocktail. These warming treats perfectly matched our winter adventure.
The offseason offered a more relaxed way to explore
During the peak summer months, Chicago becomes very busy, with popular attractions and restaurants sporting long lines and requiring a lot of planning. By visiting in December, we avoided all the typical tourist crowds and had a much more relaxed trip.
We were hoping for snow, but although it was cold, it never rained or snowed. By the end of our week, we had transformed into winter warriors. On the day we departed, it was 40 degrees and felt almost warm. In true Chicago spirit, one of the kids even wore shorts – he had become a true Chicagoan!
The magical combination of festive atmosphere, smaller crowds, and unique winter activities made it an ideal time to visit the Windy City – even for a family of Australians used to a hot December spent on the beach.
