I wholeheartedly believed in Santa Claus when I was a little girl. That could have been where the love for Christmas started- gifts, the lights, the magic. In the same way that Chicagoan’s are die-hard Cubs fans, even when losing, I was a fan of Christmas. It’s the most thrilling time of year. I have found memories of decorating the Christmas tree and seeing the Nutcracker Ballet. It was pure magic. Even now that I am older, I can’t wait for Christmas season again.
Luckily, I live in Chicago where Christmas is a spectacle. The whole city glows. The trees along the Magnificent Mile glow and the stores are decorated floor to ceiling with ribbon and weather. Before you book your ticket to New York City, consider visiting Chicago for the holidays this year. If you are from out of town visiting relatives or simply traveling, here is my recommended Christmas Itinerary in Chicago.
Christmas Itinerary in Chicago
Day 1
Morning: Brunch at Wildberry & Ice Skating at Maggie Daley Park
I’m the type of person who wakes up already thinking about coffee and breakfast. While traveling or on vacation I never want to begin the day too early. Start your day with a leisurely brunch at Wildberry, where you can savor a classic American breakfast of fluffy pancakes, eggs, and crispy bacon. A breakfast paired perfectly with a steaming cup of coffee. Once you fue up, head out for a morning of exploration at Millennium Park, where you can see The Bean and the giant Christmas Tree. Following this up by a gliding across the ice at Maggie Daley Park.
Afternoon: Lunch at The Walnut Room at Macy’s State Street & Shopping on Magnificent Mile
Ever wonder what 45 feet looks like? Neither did I—until I saw it for myself. After a cozy lunch in the Walnut Room, you’ll know too. Standing tall at 45 feet, Macy’s giant Christmas tree is breathtaking. Macy’s truly captures the magic of Christmas—just like the classic Miracle on 34th Street. But the holiday spirit doesn’t end there. Chicago’s Magnificent Mile, adorned with twinkling Christmas lights, is the ultimate spot to soak up the festive vibes and tackle your holiday shopping. Don’t miss it!
Evening: Dinner at Labriola & Zoolights at Lincoln Park Zoo
A visit to Chicago wouldn’t be complete without trying a slice of deep-dish pizza, and I know just the place. Labriola, conveniently located off Michigan Avenue, is one of my favorite spots in the city. It’s my go-to recommendation for out-of-town guests, offering a consistently great experience with minimal wait times. In my opinion, their pizza outshines Lou Malnati’s, making it a must-visit for any pizza lover. Be sure to order a side of garlic knots as well.
Wrap up your day with a visit to the Christmas lights at Lincoln Park Zoo. Visiting the ZooLights at Lincoln Park Zoo is a holiday tradition that never gets old. You’ll encounter everything from glowing animal sculptures to synchronized light shows set to classic Christmas songs.
Day 2
Morning: Brunch at Lou Mitchell’s & Museum of Science and Industry Christmas Tree Exhibit
Nothing says Christmas to me more than a hearty meal. Start your second day of Christmas in Chicago with brunch at Lou Mitchell’s, a charming and cozy spot known for hearty breakfast plates and the best pancakes in town. I always order the Denver omelet, but there are many options.
Make your way to the Chicago Museum of Science and Industry for their annual “Christmas Around the World and Holiday of Lights” exhibit. This stunning display features hundreds of beautifully decorated Christmas trees, each representing different cultures and traditions. Incredible. The attention to detail and creativity will inspire you to add a little extra sparkle to your Christmas tree at home.
Evening: Dine at RPM Italian & see the Nutcracker Ballet at the Lyric Opera House
Spend your final night of this Christmas Itinerary in Chicago seeing the timeless classic, Nutcracker Ballet. But before you head over to the Lyric Opera House, dine with RPM Italian. The Nutcracker is beloved show and one of my favorite holiday memories since childhood. I remember being young, taking the train into the city from my grandma’s house. It never fails to captivate e. The dancers, even the rat king, are exquisite, and the music is enchanting. The stunning performance, paired with the grand architecture of the Lyric Opera House, is the perfect way to immerse yourself in the holiday spirit and create lasting memories. You will be listening to Tchaikovsky all the way home.
Night– Frosty’s Pop-Up Holiday Bar (15 minute drive from Lyric Opera House)
Keep the festivities alive with a visit to Frosty’s Pop-Up Holiday Bar. Sip on a Christmas-themed cocktail while soaking in the vibrant holiday atmosphere, complete with dazzling colorful lights and live music or a DJ. This three-story wonderland is packed with holiday cheer. Every inch of the walls and ceilings adorned with ornaments and lights. It’s the ultimate spot to celebrate the season and the perfect way to wrap up your Chicago adventure.
Follow this Christmas Itinerary in Chicago. I know you will have a great time. Enjoy experiencing this great city at the best time of year.
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