Chicago lights up like nowhere else when the holidays arrive. The city transforms into a winter playground where streets twinkle, aromas of hot cocoa drift through the air, and every corner hums with excitement. Every neighborhood has surprises—Santa visits, glowing shows, and playful traditions that families return to year after year.
Chicago’s holiday season isn’t just a time on the calendar—it’s a celebration that wraps children in wonder, laughter, and memories they can carry well beyond the winter chill.
Christkindlmarket

Imagine stepping into a scene straight out of a fairy tale. The Christkindlmarket in Chicago brings that magic to life with its European charm.
Kids can sip on warm mugs of hot cocoa while parents explore handcrafted gifts. The vibrant decorations transform Daley Plaza into a festive wonderland.
The market isn’t just about shopping; it’s an experience filled with German treats and joyful carolers. Children can also enjoy the Kinder Club activities, making crafts and learning about cultural traditions.
Ice Skating at Millennium Park

Spinning gracefully or struggling to stay upright, ice skating at Millennium Park is a cherished holiday tradition.
The rink, nestled under the iconic Chicago skyline, offers a picturesque setting for families. Kids love the thrill of gliding across the ice, often creating their own laughter-filled races.
After skating, families can warm up with steaming cups of hot chocolate from nearby vendors. It’s an experience that combines physical activity with festive cheer, creating lasting memories.
ZooLights at Lincoln Park Zoo

ZooLights at Lincoln Park Zoo turns the ordinary into the extraordinary. The zoo becomes a canvas of vibrant lights, enchanting visitors of all ages.
Kids can wander through illuminated pathways, spotting their favorite animal figures glowing in the dark. Interactive light displays add an element of wonder and excitement.
The holiday atmosphere is further enhanced with seasonal treats and warm beverages, making it a delightful winter evening for families. It’s an illuminating adventure that captures the imagination.
Navy Pier Winter WonderFest

At Navy Pier’s Winter WonderFest, joy meets imagination. This indoor extravaganza is a paradise for kids, offering rides, slides, and more.
Children can explore a snowy wonderland filled with holiday-themed attractions. The excitement is contagious as they race down slides or spin on carnival rides.
With festive decorations all around, the experience is both magical and thrilling. It’s a perfect escape from the chilly outdoors, providing endless entertainment and fun.
Macy’s Holiday Windows

Macy’s holiday windows are a tradition that captures the imagination of children and adults alike. Each window tells a story, filled with intricate details and vibrant characters.
Kids press their noses against the glass, captivated by the magical scenes. The artistry and creativity behind each display spark endless curiosity and wonder.
This visual feast is more than a shopping experience; it’s a celebration of storytelling and holiday spirit. Families gather to admire the windows, igniting dreams and festive joy.
Chicago Toy & Game Fair

For young minds eager to explore, the Chicago Toy & Game Fair is a playground of possibilities. Here, kids can discover the latest toys and games.
Interactive exhibits invite children to try out new creations, fostering creativity and imagination. It’s an opportunity to meet toy inventors and learn the stories behind favorite games.
This annual event is more than just fun; it’s a chance for kids to dive into innovation and creativity. The fair creates a vibrant atmosphere of exploration and discovery.
Holiday Train on the CTA

Riding the CTA Holiday Train is a whimsical journey that delights children and adults. The train is adorned with festive lights and holiday decorations.
Kids’ eyes light up as they step inside, greeted by cheerful music and Santa Claus himself. The train ride becomes a moving celebration of holiday cheer.
This unique experience turns an ordinary commute into an extraordinary adventure, spreading joy and excitement throughout the city. It’s a tradition that brings smiles and festive spirit to all.
Art Institute’s Thorne Miniature Rooms

The Thorne Miniature Rooms at the Art Institute offer a glimpse into tiny worlds filled with charm and wonder. Children are captivated by the intricate holiday decorations.
Each room tells a story, capturing historical settings in exquisite detail. Kids love the experience of peering into these miniature worlds, sparking curiosity and intrigue.
This visit is both educational and enchanting, offering a unique perspective on history and artistry. It’s a small world filled with big surprises for young minds.
Holiday Magic at Brookfield Zoo

Holiday Magic at Brookfield Zoo is an extraordinary experience that blends wildlife with holiday cheer. The entire zoo is adorned with millions of sparkling lights.
Kids can wander through glowing pathways, encountering lit-up animal exhibits and festive decorations. The event features entertainment, caroling, and seasonal treats.
It’s a magical evening where nature meets the spirit of the season, providing endless wonder and joy for children and families alike. The zoo becomes a lively celebration of lights and nature.
The Santa Suite at Swissotel

In the heart of Chicago, the Santa Suite at Swissotel offers a luxurious holiday experience. This lavishly decorated suite invites children into a world of splendor.
Kids can meet Santa Claus, sharing wishes and capturing memories with photos. The suite is adorned with festive decorations, creating a magical ambiance.
Families enjoy the opulent setting, making it a special holiday outing. It’s an experience that combines elegance with the enchantment of meeting Santa, creating cherished memories.
Sledding at Soldier Field

Sledding at Soldier Field is an exhilarating winter activity that kids eagerly anticipate. The snowy slopes offer thrills and laughter as children race down.
With the iconic stadium as a backdrop, the experience is both fun and uniquely Chicago. Families gather to enjoy the simple joy of sledding.
This outdoor adventure is a perfect way to embrace the winter season, creating memories filled with laughter and excitement. It’s a tradition that brings joy to children and parents alike.
Winterland at Gallagher Way

Winterland at Gallagher Way transforms into a festive paradise for kids. With ice skating, holiday markets, and entertainment, it’s a hub of seasonal joy.
Children can glide on the ice or explore the festive surroundings. The atmosphere is lively, with holiday music and decorations enhancing the experience.
Families can savor seasonal treats and enjoy the vibrant community spirit. This dynamic event creates a warm and welcoming holiday environment for all ages.
The Nutcracker at Joffrey Ballet

The Nutcracker by Joffrey Ballet offers a magical journey into a world of dance and fantasy. The beloved ballet enchants children with its captivating story.
The colorful costumes and lively performances bring the tale to life, capturing the imagination of young audiences. It’s a theatrical experience filled with wonder.
For many families, attending The Nutcracker is a cherished holiday tradition, sparking joy and appreciation for the arts. It’s a celebration of creativity and holiday magic.
Christmas Around the World at MSI

At the Museum of Science and Industry, ‘Christmas Around the World’ presents a global holiday journey. Kids can explore diverse cultural traditions.
The exhibit features beautifully decorated trees, representing countries from around the globe. Children learn about different customs and celebrations.
Interactive displays and engaging storytelling enhance the experience, providing a rich and educational exploration of global holidays. It’s an enlightening adventure that broadens young minds.

