Chicago, 2024
Chicago at Christmastime feels like a city that knows exactly how to lean into winter rather than fight it. The air is crisp, the lights come on early, and the streets hum with a mix of holiday cheer and everyday city life. It is festive without being precious, bold without being overwhelming, and unmistakably Chicago.
Our first stop was Millennium Park, where the city’s iconic Cloud Gate, better known as the Bean, reflected the season back at us. Christmas lights shimmered across its mirrored surface, capturing the skyline, bundled-up visitors, and the quiet excitement that seems to hang in the air downtown in December. Nearby, the city’s Christmas tree stood tall, anchoring the park in classic holiday fashion.
Chicago’s food culture feels even more essential in winter, and we leaned into it. A visit to the legendary Billy Goat Tavern delivered exactly what you hope for. Simple, loud, and full of character, it felt like stepping into a piece of Chicago history, one cheeseburger at a time. Later, we did things a little more polished at Gibson’s, where the warmth inside contrasted perfectly with the cold streets outside. It was the kind of place that feels timeless, especially during the holidays, when a great meal becomes part of the memory of the trip itself.
One of the highlights of the visit was an afternoon with the Chicago Symphony Orchestra. There is something deeply fitting about hearing world-class music during the holiday season, especially in a city with such a strong cultural backbone. Sitting in the hall, wrapped in winter coats and anticipation, felt like a reminder that Chicago’s creative spirit shines brightest when the nights are longest.
Of course, no trip to Chicago is complete without deep-dish pizza. Lou Malnati’s lived up to its reputation, delivering comfort food at its finest. Rich, indulgent, and unapologetically filling, it was the perfect way to end a cold day of walking the city.
Chicago at Christmas is not about escaping winter. It is about embracing it. Between iconic sights, legendary meals, and moments of music and warmth, the city offers a holiday experience that feels grounded, authentic, and deeply memorable.
