Our family journeyed from Australia to Chicago, discovering the joys of offseason travel amidst winter festivities and fewer crowds.
We dove into winter activities like ice skating and curling, making our offseason trip unforgettable. Friends warned us about the cold, but we were determined to experience a real American Christmas. In Australia, December means heat and late sunsets, so we craved that classic winter vibe.
Our first day was a shocker, hitting the coldest temperature of the year. Even locals were shivering! But we had a five-hour walking tour lined up with a local guide named Bill. He was in his 70s and full of energy, showing us that Chicago’s charm shines even in the cold.
We had a blast exploring the city, and Bill shared great stories and tips for our week. While we usually enjoy seafood and beach trips for Christmas, Chicago gave us that movie-like holiday experience we always dreamed of.
We checked out the Lights at Lincoln Park Zoo, wandered through the Christkindl market, and found some festive pop-up bars. The kids loved visiting the Hanukkah bar, 8 Crazy Nights, too. Our ice skating skills weren’t the best, but the stunning city views made up for it.
I was hesitant about an architecture river tour, thinking the cold would ruin it. But Bill convinced us, and we found a 90-minute cruise that turned out to be fantastic. The gray skies even made for dramatic photos!
With Christmas approaching, the city buzzed with entertainment. We caught a Chicago Bulls game, cheering for fellow Aussie Josh Giddey, and saw the Blue Man Group. The highlight for me was visiting Second City, where I’d taken online courses during lockdown. My kids were worried I’d jump onstage, but I managed to stay put!
The cold weather was perfect for indulging in Chicago’s comfort food. We devoured deep-dish pizza at Giordano’s, which quickly became our favorite, and enjoyed authentic Italian beef sandwiches and Chicago-style hot dogs. The kids loved the hot chocolate, while my wife and I warmed up with mulled wine.
Visiting in December meant we avoided the summer crowds, making our trip much more relaxed. We hoped for snow, but it stayed dry and cold. By the end of the week, we felt like winter warriors. On our last day, it was 40 degrees, and one of the kids even wore shorts—he was officially a Chicagoan!
The mix of festive vibes, fewer tourists, and unique winter activities made it the perfect time to visit the Windy City, even for a family of Australians used to hot December beach days.
