How My Family Found Holiday Joy in the Magical City of Chicago

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by Kelle Hampton

Although I've lived in Florida for 13 years, I can say with certainty that my heart belongs in the Midwest. If there’s one time of year I feel a throbbing reminder of this, it’s Christmas. I faithfully abide by the “It is what you make it” rule, but even with my holiday freak flag unfurled to “fully festive” (cue reindeer socks, twinkle lights, and “It’s the Most Wonderful Time of the Year” on a 24-hour loop), there isn’t a gingerbread-baking session in the world that competes with the cozy holiday scenes I remember—huddled by the fire in Fair Isle sweaters as the snow fell outside. Every year, I attempt to recreate that magical holiday feeling.

But last year, I had had enough of the sound of lawnmowers and the sight of flip-flops while attempting to watch White Christmas. That was it. I was taking my family to the Promised Land of Christmas—a weekend in the place that, to me, holds all the storybook magic of the holidays … Chicago.

To say the city lived up to my expectations that December weekend would be an understatement. In fact, a few hours into walking the snowy streets and watching with tears as my kids oohed and ahhed over all the Christmas trees in apartment windows and horsedrawn carriages and choirs singing carols on street corners, I knew I had done something dangerous—given them the opportunity to experience something so wonderful, something so magical, they'd want to return every year.

Of course, when I experience something that good in life, I want others to feel it, too. The holidays are about sharing, after all. So as the self-proclaimed holder of my made-up title as December Ambassador of Chicago, let me lead you through my favorite holiday wonders hidden in The Windy City.

Macy’s on State Street and the Walnut Room

It begins with the storefront windows—their elaborate displays depicting holiday scenes plucked straight from the storybooks—and continues inside among the eight floors, each with its own highlight of the holidays: Santa on the 6th floor, Holiday Lane on the 7th, and the world-famous Walnut Room and its epic Christmas tree on the 8th. This store reminds me of the scene in the movie Elf, when Buddy stays up all night and creates a Christmas wonderland in a department store. To me, Macy's in Chicago is like Buddy's creation, a place children will never forget and a place where, at least for a day, any adult can return to the wonder of childhood.

John Hancock Building 360 Chicago Observatory

360 Chicago is the best way to get a reindeer's-eye view of Chicago and take in the wintery city scene without having to wear a coat. We arrived when they opened and practically had the entire observatory floor to ourselves for a few moments. As holiday music filled the room, we felt warm and cozy inside while we looked out at the wintery scene below, making it feel like we were living inside a snow globe. Order an Irish coffee in the observatory café and try the Tilt experience, a ride that tips you past the window view.

The historic Chicago Water Tower lit up for the holidays

City Sidewalks, Busy Sidewalks

You don’t need fancy attractions to feel the holiday spirit when Chicago’s city sidewalks hold the essence of the magic. Michigan Avenue’s lights turn on during The BMO Harris Bank Magnificent Mile Lights Festival on November 18, 2023, but the holiday flame stays lit throughout downtown for the entire season with street performers, horse-drawn carriages and festive storefront displays. Our favorite memories of our trip were made simply walking, especially at night, listening to carolers on corners, finding side streets with Christmas trees visible through the windows of charming brownstone apartments, and popping in coffee shops for hot cocoa warm-ups. While you’re shopping and taking in the sights, stop by Garrett Popcorn for a famous Chicago snack, take a carriage ride near Water Tower Place for a special winter treat, and make sure you visit one of the city’s beautiful churches to whisper your holiday gratitude by candlelight.

Ice Skating in Millennium Park

Ever wished you could climb into one of those ceramic Christmas village scenes? Here’s your chance. The iconic McCormick Tribune Ice Rink at Millennium Park is free and open to the public ($10 skate rental). With the skyline backdrop and twinkling tree lights surrounding the rink, you’re sure to make a winter memory…even if you fall. If you do happen to take a spill, you can nurse your broken pride with hot dogs and hot cocoa at The Park Grill.

Christkindlmarket

A truly unique holiday shopping experience, Christkindlmarket is a large open-air festival inspired by the famous holiday market founded in Nuremberg, Germany, in 1545. Celebrating European traditions and offering fine handmade gifts that can’t be found in traditional retail shops, the market has become a favorite holiday ritual for locals and tourists alike. Sip spiced wine and sample Strudel and potato pancakes while you shop. Along with Daley Plaza in downtown Chicago, Christkindlmarket has two other locations for the season: one in The Park at Wrigley in Chicago's Wrigleyville neighborhood and one in the western suburb of Aurora.

The Holiday Train

With their seasonal décor, festive lights, and costumed conductors, Chicago’s Polar Express™ Train and the CTA Holiday Train hold all the (jingle) bells and whistles of a unique holiday experience. But for tourists who are unfamiliar with big-city life (that’s us), even a simple train ride from one station to the next can be a special experience. We picked up hot cocoa for our ride and listened to a street performer's rendition of “Joy to the World” on the platform before boarding a train for our own wintery tour of the city. As the train emerged from the subway, we watched the skyline move out the windows, making the city feel alive in the distance. Later, my kids talked as much about that train ride as about the events that required more planning on my part. As any parent knows, you take what you can get.

The outdoor Christkindlmarket in Chicago

For tourists delighted by the unfamiliarity of big city life, a simple train ride delivers its own excitement.

Between each of these Chicago treasures are countless more holiday gems, from cozy taverns tucked into the city streets to the cheerful spirit of the people who come from far and wide to experience its dazzle. While we stood on the corner of State Street and Chestnut last year, fat snowflakes falling fast around us, my daughter whispered to me, “I feel like we’re in a Christmas movie, Mom.” I felt it, too.

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How My Family Found Holiday Joy in the Magical City of Chicago

by Kelle Hampton

Macy’s on State Street and the Walnut Room