- I took my family from a 95 degree Australian summer to experience Chicago’s 5 degree winter weather.
- Everyone warned us that 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 off-season trip unforgettable.
Despite warnings from friends and fellow travelers, we decided to spend the December holidays in Chicago.
Almost 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 another goal: to experience a real American Christmas. In Australia, where we live, December means blistering heat and late sunsets that make holiday light displays virtually invisible until 10pm.
Despite the cold weather, it was an unforgettable experience.
We had an extreme welcome to the Chicago winter
Our first day coincided with the city’s coldest temperature of the year – just 5 degrees Fahrenheit. Even the natives of Chicago shivered and complained of the brutal cold.
Despite the Arctic blast, we had planned a five-hour walking tour through the Chicago Greeters program, a free service that matches visitors with local volunteers. Bundled up 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 typical Christmas involves trips to the beach and seafood, growing up watching movies like Home Alone gave us a different vision of the holiday season. Chicago delivered that perfect movie-like Christmas experience with a magical wintery atmosphere that we had always dreamed of.
We explored the Lights at Lincoln Park Zoo, wandered through the charming Christkindl Market, and discovered some festive Christmas bars in Wrigleyville. As a special treat for our half-Jewish children, they were excited to visit the Hanukkah bar, the 8 Crazy Nights.
Although our skating skills left a lot to be desired, the stunning cityscape surrounding the Maggie Daley Ice Rink more than made up for the spills.
Architecture tours impress even in winter
One thing I was reluctant to do was an architecture tour on the river. While the city is famous for its buildings, I worried that the cold would make it unbearable. But Bill convinced us to do it.
Although many operators were closed for the season, we found a 90-minute cruise. Surprisingly, despite the wintry conditions, this was a great tour and even the kids enjoyed it. Moody gray skies made for more dramatic photos.
After dark, the city came alive with a festive spirit
Being close to Christmas, the city offered endless possibilities for entertainment. We went to a high-energy Chicago Bulls game where we were extremely excited to support fellow Australian Josh Giddey, complete with handwritten signs to cheer him on.
The author and his family made the most of their winter trip to Chicago. Courtesy of the author
We also saw the Blue Man Group perform, but the highlight for me was visiting Second City. After completing several online satire writing courses with them during the COVID lockdown, it felt like a pilgrimage to see a live show. My kids were worried that I was going to jump on stage, but despite my best efforts, it didn’t happen.
Chicago’s winter weather calls for comfort food
The chilly temperatures gave us the perfect excuse to indulge in the city’s tastiest dishes. We ate deep dish pizza at Giordano’s (which quickly became our favorite), enjoyed authentic Italian beef sandwiches, and enjoyed Chicago style hot dogs.
The author’s family enjoyed the foods Chicago had to offer. Courtesy of the author
The kids loved enjoying the endless selection of decadent hot chocolate, while my wife and I warmed up with mulled wine and Tom & Jerry’s, a Midwestern holiday cocktail. These warming treats matched our winter adventure perfectly.
The off-season offered a more relaxed way to explore
During the peak summer months, Chicago gets very busy, with popular attractions and restaurants sporting long lines and requiring a lot of planning. 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, neither rain nor snow fell. By the end of our week, we had transformed into winter warriors. The day we left, it was 40 degrees and I almost felt warm. In true Chicago spirit, one of the kids was even wearing shorts – he had become a true Chicagoan!
The magical combination of festive atmosphere, smaller crowds and unique winter activities make it an ideal time to visit the Windy City – even for an Australian family used to a hot December spent at the beach.
