Chicago at Christmas | Clarence & Pinafor

The guide

Chicago

Christmas trip · Chicago, USA

The Wrigley Building dressed in Christmas garlands.

Getting there

Chicago at Christmas is a classic college-break road trip — or an easy Amtrak ride into Union Station. Flying in? The CTA Blue Line train runs from O'Hare to downtown in under an hour. The Christkindlmarket fills Daley Plaza at 50 West Washington Street, right in the Loop — an easy walk or short train ride from anywhere central.

Famous for

Chicago's Christkindlmarket is the most German-feeling Christmas market in America — because it was built that way. It opened in 1996 (at Pioneer Court, moving to Daley Plaza in 1997), inspired by the famous Christkindlesmarkt in Nuremberg, Germany, and run with the German American Chamber of Commerce. More than a million visitors come each year, entry is free, and the red-and-white striped stalls sell everything from nutcrackers to the collectible Glühwein mugs everyone queues for. The season runs from the Friday before Thanksgiving to Christmas Eve.

The Chicago Theatre marquee, glowing on State Street.

Where to eat

Bratwurst, currywurst, potato pancakes, strudel and hot Glühwein at the market — then do as Chicago does and finish with a deep-dish pizza, all cheese and tomato and taller than your thumb. Warm, filling, and exactly what a freezing December evening demands.

What to do

Wander the market stalls under the Daley Plaza Christmas tree, say hello to the Picasso sculpture (a Chicago landmark since 1967), and look up at the glowing Chicago Theatre marquee on State Street. Millennium Park — the Bean, the ice rink, the city Christmas tree — is a short walk east, and the Magnificent Mile sparkles all season.

Hand-blown baubles, the kind sold at the Christkindlmarket stalls.

Chicago deep-dish pizza — essential eating after the market.

Jess's favourite

Lincoln Park ZooLights

Jess's favourite: ZooLights at Lincoln Park Zoo, when the whole zoo glows with more than three million lights. Sip hot chocolate, walk the light tunnel, and visit with Santa — the animals get their own quiet winter's rest while the lights do the show.

Good to know: entry to the Christkindlmarket is free. It runs from the Friday before Thanksgiving through Christmas Eve, and it gets busiest on December weekends — weekday afternoons are calmest. Wrap up warm: Chicago in December means business.

Jess always checked the market dates on the official website before travelling — opening days can shift from year to year. And pack your warmest coat for Chicago in December.

Read Jess's diary of the day ↓

Jess's Christmas Adventures · Diary No. 7

Chicago: Glühwein, Deep-Dish, and a Market Since 1996

Christmas, eight years ago

Chicago in December is cold. Not ordinary cold — the serious kind, the kind that makes your cheeks tingle and your breath puff out in clouds. And honestly? It makes the Christkindlmarket better. Hot Glühwein has never tasted so good as it does when it's freezing.

Daley Plaza was exactly like the pictures: red-and-white striped stalls, the smell of bratwurst and roasted almonds, and that big Christmas tree in the middle. The market has been here since 1997 (it started at Pioneer Court in 1996), and it's modelled on Nuremberg's famous market — you can feel the German-ness in every stall. I queued for the collectible Glühwein mug like everyone else. Worth it.

I said hello to the Picasso sculpture — a giant rust-red abstract beast that's been puzzling Chicagoans since 1967 — and then walked to the Chicago Theatre, all lit up on State Street. That marquee at night is pure old-Hollywood magic.

Dinner was deep-dish pizza, because when in Chicago. It arrived looking like a pie and ate like a hug. I sat by the window watching the snow start and thought about how far from home I was — and how completely at home I felt.

The evening ended at Lincoln Park Zoo, where ZooLights turns the whole place into three million twinkling lights. I walked the light tunnel twice. Some nights you don't want to go home. This was one of them.

Barnaby's text“Brave the cold and the cold rewards you, Jess. Warm drinks taste warmer, lights shine brighter, and pizza — well, pizza is always a good idea.”

— Jess

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