Windy City Wonderland

Windy City Wonderland

A Chicago Christmas is Unlike Any Other

By Sydni Ellis

Stepping out of Chicago’s Midway Airport in 2016, I was greeted by soft snowflakes tickling my nose and covering my hair in white. It was the first time my husband and I had returned to the place we met since getting married, and the magical snow greeting was all it took to clear my travel weariness and make me excited for a vacation in Chicago at Christmastime! This city holds a special place in my heart this time of year, because it reminds me of romance — holding hands while sipping hot cocoa, dressing up for The Nutcracker, and kissing under the mistletoe. Returning after a few years, now married, just enriched the experience and led us to even more wonderful moments along the way.

If you’ve ever been to the Windy City, then you know how awesome it is. Chicago has won Condé Nast Traveler’s Best Big City in the U.S. Readers’ Choice Award for the last five years in a row thanks to its amazing transportation, world-class live events, fantastic food options, historical museums, amazing outdoor areas, and phenomenal festivals. But visiting during the holiday season is somehow even better. Twinkling lights are strung all around, Christmas trees sparkle on every corner, and everyone seems to be in a festive mood while shopping, strolling through a holiday festival, and sipping delicious hot cocoa. It feels like a scene out of a Hallmark movie.  

I fell in love with my now husband after a December-in-Chicago vacation, and  now we go back every chance we get. The best part is it’s a pretty inexpensive vacation. Due to the cold weather (including those magical snowflakes), plane tickets and hotel stays are actually more affordable this time of year, so you can soak up all the holly jolly vibes without breaking the budget! Here are fun things you can do during a three-day weekend this month.

Check-in at the historic Warwick Allerton, located at 701 North Michigan Avenue. This 1920s jazz hotel has become a famous Chicago skyline landmark, and it has been renovated to offer all the modern amenities your heart desires. This beautiful, four-star hotel is timeless and elegant, offering a warm, comfortable stay in a prime location on Chicago’s famed Magnificent Mile. Prices in November are as low as $81 per night on select dates. Yes, seriously! Reserve your spot at

After dropping off your bags — and piling on your scarves, hats, gloves, and coats — it’s time to go shopping on the Magnificent Mile. More than 450 retailers are set up here, from international designers to flagship experience to major department stores. If you get cold, drop in the Ghirardelli Ice Cream & Chocolate Shop inside the Wrigley Building at 400 North Michigan Ave. Everything on their menu is good, but you can’t go wrong with the heavenly Decadent Drinking Chocolate ($5.50), made with melted Ghirardelli dark chocolate chips and topped with whipped cream.

If you are there on November 20, stay for the 30th Anniversary Magnificent Mile Lights Festival. Mickey and Minnie Mouse from Walt Disney World will host this event that illuminates more than one million lights on 250 trees along the Mag Mile for this must-see spectacular day. The festival begins at 11 a.m. with free, family-friendly activities, cheesecake from Eli’s Cheesecake Company, a holiday DJ, photos with Santa Claus and more. Then at 5:30 p.m., watch the parade beginning at Oak Street and Michigan Ave., traveling south to Wacker Drove. An amazing fireworks display will happen at 7 p.m. over the Chicago River to usher in the merry holiday season. Learn more at

This year marks the 25th anniversary of the iconic Christkindlmarket in Chicago, happening at Daley Plaza, 50 West Washington Street, from November 19-December 24, and Gallagher Way, 3635 North Cark Street, from November 19-December 31. Modeled after the traditional holiday markets in Europe, Christkindlmarket is a unique shopping experience. This free outdoor event features live entertainment (including old-fashioned carolers!), mulled wine and other treats from Germany, hot apple cider served in one-of-a-kind souvenir mugs, handmade ornaments, and other wonderful gifts you can’t find anywhere else.

On the nearby State Street, you should stop by the Macy’s department store to see the fabulous holiday window display, featuring animatronic characters, music, and beautiful holiday scenes for passers-by to enjoy. Later, make reservations for a table at The Walnut Room inside this Macy’s, where you will be served holiday favorites in an elegant dining room with a view of the spectacularly decorated indoor Christmas tree. Reserve your spot at

Next on your Christmas in Chicago bucket list is checking out the holiday celebrations at Millennium Park. Go ice skating in the McCormick Tribune Ice Rink, opening November 19-March 6, 2022. While you’re skating, you’ll be surrounded by twinkling lights, stunning downtown buildings, and a view of Cloud Gate, aka The Bean. Next, watch the stunning 108th Annual City of Chicago Christmas Tree Lighting Ceremony in Millennium Park, which will happen at 6 p.m. November 19 and stay lit through January 9. Finally, don’t miss the Millennium Park Holiday Sing-Along from 6-7 p.m. November 26, December 3, 10, and 17. You can sing along to holiday bops celebrating Chicagoans’ many faith backgrounds, cultures, and music traditions. Learn more about these holiday celebrations at

For more lights and holiday magic, visit the Christmas Around the World and Holidays of Light exhibit at the Museum of Science and Industry Chicago. This is my favorite place to experience holiday joy. It features a four-story Grand Tree surrounded by more than 50 trees and displays decorated by volunteers to represent many holiday traditions from around the world. Admire the uniquely decorated trees throughout the exhibit, which is included with your museum admission and open from November 17-January 3, 2022. Snag tickets at

There’s a new experience at Navy Pier that holiday lovers will not want to miss. Light up the Lake, taking place from November 26-January 2, features indoor light sculptures comprised of 600,000+ twinkling lights. These will be in fun shapes, like toy boxes, a giant teddy bear, a deer, a light tunnel, and a huge tree. There will also be an Alpine ice rink, a holiday beer garden, kiddie train rides, Santa’s Village, gift market, and more. Each ticket comes with a free ride on the Centennial Wheel on the Pier, which will be decorated for the season. You can also reserve a spot for a sit-down holiday dinner, complete with signature cocktails and seasonal brews.

Another place to see lights is at the Lincoln Park Zoo, which is hosting ZooLights November 19-January 2. This fun-for-the-whole-family event is free on Mondays and Tuesdays and just $5 Wednesdays-Sundays includes hundreds of LED displays and experiences that glow under millions of lights throughout the zoo. New this year is an 18-foot holiday tree inside the Pepper Family Wildlife Center, a Light up the Lawn show on the South Lawn, and a reimagined Enchanted Forest. You can also sip on spiced wine or frosty beers, try out the Snowy’s Spirits & S’more Pop-up Holiday Bar, and go through the dazzling light maze.

In the evening, see one of the many wonderful holiday shows put on this time of year. You can see Charles Dickens’ A Christmas Carol at the Goodman Theatre November 20-December 31; ‘Twas the Night Before by Cirque du Soleil at The Chicago Theatre from November 26-December 5; The Nutcracker at the Joffrey Ballet December 4-26; and Hershel and the Hanukkah Goblins at Rivendell Theatre November 20-December 12.

With so much to see and do, Christmas in Chicago will quickly become your new favorite holiday tradition!

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