I was worried about my Australian family spending time in the cold Chicago winter. We discovered that offseason travel has benefits.
16.01.2025 - 16:09
/ insider.com
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.
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.
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.
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.
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.
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