Holiday Travel in Chicago: Where To Go and What to Do
Travel expert Darley Newman at the Magnificent Mile Lights Festival in Chicago.
From rooftop ice skating with city views at The Peninsula Hotel to tasting festive treats at the Museum of Ice Cream, discover Darley’s top 5 holiday experiences in Chicago.
Kicking off the holiday season, Darley recently traveled to Chicago to attend The Magnificent Mile Lights Festival, walking and riding in the parade. Darley was also featured live on Good Day Chicago, speaking with the charming Anita Blanton about the holiday festivities and Travels with Darley Season 12. She is now sharing her expert tips for travelers looking to experience holiday magic in the Windy City. From winter activities, to architecture, and where to find the best holiday desserts, here are Darley’s recommendations for your next Chicago adventure. See Darley in The Magnificent Mile Lights Festival here!
Tip 1: Rooftop Ice Skating at the Peninsula Hotel Chicago Start the holiday season with an unforgettable experience, ice skating, drinking hot chocolate, and gazing upon breathtaking city views at The Peninsula Hotel Chicago. Located above Michigan Avenue on the Peninsula Hotel Terrace, you can skate in a beautifully decorated winter wonderland, hangout, and enjoy delicious seasonal beverages and snacks. After you finish skating, head up to Z Bar to end the day with a cocktail and even more fantastic Chicago views.
Tip 2: Try Something Sweet at the Museum of Ice Cream and Nutella Cafe Chicago Along The Magnificent Mile and nearby Michigan Ave, there are many places to stop in and try interesting holiday creations that are sure to satisfy your sweet tooth. During the holiday season the Museum of Ice Cream turns into a pink winter wonderland for “Pinkmas” with spirited decorations, a variety of interactive experiences, a speakeasy, and lots of tasty ice cream options. Unique to this Magnificent Mile location, you can try a classic Chicago hotdog made out of ice cream and topped with real relish and mustard. For chocolate lovers, stop by the Nutella Cafe Chicago on Michigan Avenue to create your own Nutella inspired food and beverages, and take home your favorite products.Bonus tip: Don’t miss the personalized Nutella jars- they make amazing holiday gifts for friends and family. Watch me create my own personalized jar here.
Tip 3: Find Unique Holiday Gifts at The Shops at North Bridge
Looking for somewhere to shop for holiday gifts and Chicago souvenirs? Check out
on The Magnificent Mile! In this vibrant shopping center, you can find a mix of popular national retailers as well as one-of-a-kind Chicago brands that you can’t get anywhere else.
From shopping and grabbing a happy hour cocktail at the Habitat bar inside Chicago’s flagship Nordstrom to creating a permanent bracelet to take home a piece of the city, you are sure to find something special here.
Tip 4: Explore Chicago Architecture on a CruiseNo trip to Chicago is complete without taking in the city's world-renowned architecture, which illuminates The Magnificent Mile during the winter season with bright lights and spectacular holiday decor. First head to the Chicago Architecture Center to learn about the rich history of Chicago architecture and the city’s iconic landmarks. Then, hop aboard Chicago’s First Lady to see the Chicago skyline from a new perspective. Finally, take a stroll along the Magnificent Mile to gaze upon the festive storefronts and seasonal displays.
Tip 5: Experience a Regal Afternoon TeaAfternoon tea is a tradition that invokes the holiday spirit. Stop by The Drake Hotel in Chicago for a regal experience with fragrant teas, finger sandwiches and cakes. During select dates, The Drake Hotel brings live carolers and a harpist for special performances of your favorite holiday songs. American Girl Place Chicago also offers Holiday Teatime fit for all ages to have a tea party with their favorite dolls, including tasty treats, delectable beverages, and children’s crafts.Stay tuned for more Chicago travel tips on a brand new season of Travels with Darley coming to you in January 2025. For more expert travel tips from Darley Newman, listen and subscribe to the “Travels with Darley” podcast on iHeart, Apple Podcasts, Amazon, Spotify, Podchaser, Podcast Addict, Jiosavvn, Castbox, Audible, and watch the tv series on your local PBS station, Create TV, and for free on Go Traveler!
