What To Do In Chicago For Christmas

Chicago in December is basically a giant snow globe, minus the part where someone shakes it and you lose feeling in your toes. The city goes full holiday mode with twinkling lights, hot drinks, and enough festive cheer to make even the most cynical Midwesterner crack a smile. Here’s how to soak it all up without turning into a popsicle.

Start With the Christkindlmarket (and Buy the Mug)

The Christkindlmarket in Daley Plaza is a Chicago holiday rite of passage. You’ll wander past wooden stalls selling ornaments, schnitzel, and enough sugar to power a small elf. Get the hot spiced wine or cocoa, because the souvenir mug is half the fun.

Yes, it gets crowded. Yes, you’ll accidentally elbow a stranger in a puffer coat. But that’s part of the charm, like a very festive mosh pit.

Ice Skate Under the Skyline

The McCormick Tribune Plaza rink in Millennium Park is the classic option. You can rent skates, wobble around the ice, and pretend you’re in a holiday movie when you inevitably grab the wall. The Christmas tree nearby makes for a top-tier photo op.

If you’re feeling fancy, book a skate at the Peninsula’s Sky Rink. It’s smaller, cozier, and comes with skyline views that make your wobbly ankles seem almost elegant.

Let There Be Lights. And More Lights.

Lincoln Park ZooLights turns the zoo into a sparkling wonderland, and the best part is that admission is free. You can sip hot cider while staring at glowing penguins and wondering if they know how lucky they are.

For a drive-through option, head to the Chicago Botanic Garden’s Lightscape or the Illumination at Morton Arboretum. Bundle up, bring snacks, and let someone else do the driving. It’s cold, yes, but the glowing tunnels are worth every layer.

Warm Up in a Museum

The Museum of Science and Industry’s Christmas Around the World exhibit is a holiday staple. You’ll see dozens of trees decorated to represent different cultures, and you’ll feel cultured just by walking past them. The huge Grand Tree in the rotunda is genuinely stunning.

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The Art Institute of Chicago is another cozy escape. You can stare at A Sunday on La Grande Jatte, then stare at the holiday decorations, then stare at a cup of coffee.

Eat, Drink, and Be Very Merry

Holiday Pop-Up Bars and Fancy Tea

Chicago food in winter is comfort food with a capital C. Get a deep-dish pizza and accept that you’ll need a nap afterward. Or grab an Italian beef, dip it, and question why you ever ate anything else.

For drinks, try a holiday pop-up bar. The city goes wild with themed bars featuring tinsel, fake snow, and cocktails named things like “Santa’s Little Helper.” Just pace yourself, because eggnog is sneaky.

If you want something classy, book afternoon tea at The Drake or the Peninsula. Tiny sandwiches, fancy pastries, and a pot of tea strong enough to revive you. It’s the perfect way to feel posh without actually being posh.

Catch a Show or a Game

Chicago’s theater scene shines in December. The Nutcracker at the Joffrey Ballet is a classic, and the Goodman Theatre’s A Christmas Carol will make you feel all warm and fuzzy. If you prefer laughs, check out a comedy club in Old Town.

Sports fans, you’re in luck. The Bulls and Blackhawks usually have home games, and there’s nothing like screaming for your team while wearing three sweaters. Just don’t spill your hot chocolate on the person in front of you.

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Shop Until You Drop (Then Get Cocoa)

The Magnificent Mile is lit up like a runway, and the store windows are basically art. You can buy gifts, people-watch, and duck into a café whenever your fingers start to protest. State Street also has the iconic Marshall Field’s windows, now Macy’s, and they’re still magical.

For unique gifts, hit the Christkindlmarket again or browse the shops in Wicker Park and Andersonville. You’ll find candles, jewelry, and things you definitely don’t need but absolutely want.

Take a Cozy Neighborhood Detour

Sometimes the best holiday moments happen away from the Loop. Walk around Lincoln Park, Old Town, or Bucktown to see decorated brownstones and quiet streets. It feels like a holiday card come to life.

Stop by a local coffee shop, order something with cinnamon, and watch the snow fall. If there’s no snow, just pretend.

End With a Skyline Moment

Finish your day at the Chicago Riverwalk or the lakefront, where the skyline glows against the winter dark. The cold will hit your face, but the view will hit your heart. It’s a reminder that even in freezing temperatures, this city knows how to sparkle.

So grab your hat, your mittens, and your sense of adventure. Chicago at Christmas isn’t just an event; it’s a full-contact sport of joy. And honestly? You’re going to love every chilly, cocoa-fueled minute.