Chicago at Christmas!
If you’re like me and every so often you crave a big city, Chicago is the perfect fix.
Skyscrapers. City streets. Busy people, neon signs. Holiday lights. Steam rising from grates. Food smells drifting out of doorways.
I love all of it. City living is the best.
Chicago is one of my favorites, and every year around this time, I make sure to squeeze in a couple of days to feel it again. Christmas trees. Window shopping. Walking until my cheeks are numb. And then—ducking into somewhere warm. That moment when you go from cold-cold to cozy, unwrapping yourself from a scarf inside a pizzeria or café? Nothing beats it. Truly one of the best feelings.
Every year looks a little different, but these are my favorite ways to do Chicago at Christmas.
Walk the City at Night
Cloud Gate (The Bean!) at night
Especially around Christmas. Tree lights, city reflections, the moon overhead. Cold, crowded, perfect.Millennium Park
Wander, linger, take it slow. This area always feels extra alive in December.Christkindlmarket
Warm drinks, lights everywhere, music, people bundled up and lingering. It’s festive in the best way—and an easy stop as you walk the city at night.Skating at the rink
Busy? Yes. Christmasy? Completely. A must.
Go Inside (It’s Winter, After All)
Chicago museums are ideal this time of year—warm, inspiring, and easy to spend hours in.
Museum of Contemporary Art Chicago
We went this year, and it was incredible. Bold, thoughtful, and fun to talk about after.Art Institute of Chicago
A classic. Always worth it.Field Museum
Shedd Aquarium
Museum of Science and Industry
Pick one. Warm up. Wander. Repeat.
Stay Somewhere with Character
Palmer House Hilton
Historic, grand, and especially magical at Christmas. The lobby, the Empire Room, the ballrooms—everything feels like a scene.
Or:
Stay somewhere with a view of the water.
Even in winter—especially in winter—the lake matters. Find a beach. Go see the water.
Eat Everything
Chicago in winter is made for food.
Pizza stops:
Giordano’s
Pequod’s Pizza
Other favorites:
Ed Debevic’s
Not the best food—but absolutely an experience.Banana pudding from Magnolia Bakery
Popcorn (the mix, always) from Garrett Popcorn Shops
Eat it all. Walk it off.
Why It Always Works
Chicago at Christmas is layers. Cold and warm. Loud and quiet. Big and familiar. One minute you’re bracing against the wind, the next you’re unwrapping a scarf inside somewhere cozy, wondering why this feeling never gets old.
Every year we do something different—but the energy stays the same. And when I need a city fix, Chicago always delivers.
