Christmas cheer in Chicago is amazing for families thanks to how accessible it is. While you’ve heard it all before that New York City is the most Christmas-y US city this time of year, there’s a lot to be said for its smaller, yet more “homey,” midwestern neighbor, Chicago. After all, Frank Sinatra sang about it, Clark Griswold infamously put on a festive light show, and MacCaulay Culkin celebrated the holiday here–alone. If you ask me, Chicago at Christmas is “my kind of town.”
So, what’s one to do in the festively flocked city of Chicago during the holidays? Look no further because I’ve put together an ideal schedule to celebrate your most Christmas-y days in the Windy City. Be sure to bundle up because although we have an abundance of Christmas cheer to keep you merry all night long, the one area we tend to lack this time of year is actual degrees (as in Fahrenheit)!
Christmas Eve-ish
The following schedules can be followed on Christmas Eve and Day, but can also happen anytime you find yourself in Chicago during the holiday season.
9:00AM–Breakfast at Wildberry Pancakes and Cafe
Make sure to order their signature “Berry Bliss pancakes”.
11:00AM–Ice Skating “The Ribbon” at Maggie Daley Park
Enjoy the beauty of the city skyline as you wind in and out of what the park calls Chicago’s “alpine in the city.”
1:00PM–Chriskindlemarket.
Wander the city’s beloved German holiday market. Enjoy a hot pretzel or traditional German bratwurst as you sip on glühwein and pick out a new ornament for you tree.
4:00PM–Dinner at Macy’s Walnut Room
Indulge in an early family dinner of mini pot pies or asiago crusted chicken while you take in the beauty of the famous great tree in the middle of the dining room.
6:00PM–Michigan Avenue Lights
Wander down Chicago’s Magnificent Mile to walk off dinner and wind your way down the mile-long avenue lit with a dazzling array of shimmering holiday lights.
Christmas Day-ish
10:00AM–Brunch at Ann Sather’s (Belmont location open on Christmas Day).
Make sure to order a side of their famous gooey cinnamon rolls.
12:00PM–Gallagher Way
Watch Ice Skate at Gallagher Way-right outside the iconic Wrigley Field.
1:00PM–Teddy Bear Tea at Hotel Zachary
Bring your favorite stuffed animal and (if so inclined) your kids 😉 and enjoy a traditional English tea. While the adults finish their own treats, your kids will be enjoying a happy little story in front of the cozy fire.
3:00PM– Chimes art installation
Pop back outside to take in the Chimes of Gallagher Way. A visual and audio art installation that’s sure to please both kids and parents alike.
5:00PM–Dinner at Margeaux Brasserie – Waldorf Astoria
Enjoy a fancier feast with a 3-course prix fixe family-style meal at the beautiful Waldorf Astoria.
7:00PM–Christmas caroling in the Gold Coast or Lakeview neighborhood.
Before the kids are tucked into bed, take in all the lights while enjoying your favorite hot beverage. Sing a few lines of Silent Night outside someone’s home and you might be surprised who comes out to join you.
9:00PM–Drinks at Jingle Bell Square.
Sneak away after the kids are in bed to the infamous Lost Lake to cheer the end of the holidays at Jingle Bell Square, a pop up bar that Clark Griswold would be proud of.
Merry Christmas, ya filthy animals.
*Have some extra time? Check out these additional favorites on our “List of Things To Do During the Holidays in Chicago.”
