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Best holiday activities in Chicago

Dive into the heart of Chicago's holiday spirit with this guide to the city's most enchanting seasonal festivities.

December 12, 2023
 min read
Last updated:
Jan 15

As the holiday season approaches, Chicago transforms into more than just a bustling metropolis; it becomes a canvas of festive joy and wintery charm. The city's streets and skyscrapers are adorned with twinkling lights, and the air carries the melody of holiday songs and the aroma of seasonal treats. For anyone visiting or living in Chicago, this time of year offers an array of experiences that are not just fun but are also emblematic of the city's rich cultural tapestry.

Magnificent Mile Lights Festival

This annual event is not just a festival; it's a Chicago tradition that heralds the start of the holiday season. As the trees along Michigan Avenue light up, the street turns into a sparkling corridor, setting the stage for a grand parade. Families gather, friends reunite, and strangers share smiles, all under the canopy of lights. Street performers, festive floats, and live music fill the air with an electrifying energy. This festival is a reminder of the joy and togetherness that the holiday season brings, making it a must-experience event in the heart of Chicago.


At the Christkindlmarket, you're not just visiting a market; you're stepping into a slice of European charm. Modeled after the traditional German Christmas markets, this place is a bustling hub of holiday activity. Wooden stalls brimming with handcrafted goods—from delicate ornaments to intricate toys—invite you to find that perfect gift. The scents of roasted nuts, sausages, and spiced wine fill the air, tantalizing your taste buds. As you wander through the market, wrapped in your scarf and gloves, the warmth of the community and the spirit of the season envelop you, offering a cozy respite from the winter chill.

Winter WonderFest at Navy Pier

Winter WonderFest is a dazzling indoor winter playground that transforms Navy Pier into a festive wonderland. As you step inside, you're greeted by a sea of holiday lights, giant decorated trees, and an array of festive attractions. Kids and adults alike delight in the indoor ice skating rink, while the Ferris wheel offers panoramic views of the winter skyline. The laughter and joy of families enjoying the rides, games, and holiday-themed activities fill the space, creating a lively and heartwarming atmosphere. This festival is a testament to Chicago's ability to turn the coldest season into the warmest memories.

ZooLights at Lincoln Park Zoo

The ZooLights at Lincoln Park Zoo is a magical evening adventure that transforms the zoo into an illuminated wonderland. As you walk through the gates, you're greeted by a dazzling display of over two million lights, creating a luminous journey through the animal kingdom. Themed displays, interactive light shows, and holiday crafts make this experience enchanting for all ages. The crisp winter air, the sparkle of the lights reflecting off the snow, and the sounds of holiday cheer create a whimsical atmosphere that's both tranquil and exhilarating. It's an opportunity to see the zoo in a whole new light—literally.

Ice Skating in Millennium Park

The ice rink at Millennium Park is more than just a place to skate; it's a Chicago landmark that comes alive during the holidays. Situated in the shadow of the iconic Cloud Gate sculpture, the rink offers a unique urban skating experience. Whether you're lacing up your skates for the first time or showing off your pirouettes, the rink is welcoming to all. Surrounded by the city's majestic skyscrapers and the festive buzz of the park, every lap around the ice feels like a celebration of winter in the city. It's a place where memories are made, against the backdrop of Chicago's stunning skyline.

Holiday Theatre Magic

Chicago's holiday theater scene is a vibrant showcase of the city's artistic spirit. From classic performances like "The Nutcracker" to innovative new plays, the city's theaters come alive with the magic of storytelling. The sound of orchestras tuning their instruments, the rustle of costumes, and the hush that falls over the audience as the curtain rises all contribute to the enchantment. Each performance, whether it's a heartwarming tale or a comedic romp, captures the essence of the season. It's a chance to sit back, relax, and be transported to another world—a world woven from the threads of imagination and holiday spirit.

The Great Tree at Macy's

The Great Tree at Macy's on State Street is a towering beacon of holiday spirit. Standing over multiple stories high, this majestic tree is adorned with thousands of sparkling lights and hundreds of ornaments. It's not just a decoration; it's a landmark that has been a part of Chicago's holiday tradition for over a century. Families and friends gather around the tree, capturing photos and marveling at its grandeur. The tree serves as a reminder of the season's joy and the lasting memories that come with it. It's a symbol of the festive spirit that envelops the city, drawing people together in shared wonder and delight.

Holiday Trolley Tours

The holiday trolley tours offer a cozy and charming way to explore Chicago's festive lights and decorations. Wrapped in a warm blanket, sipping hot chocolate, you're taken on a journey through the city's most beautifully decorated neighborhoods. The trolley's gentle rumble and the tour guide's cheerful narration add to the experience, making it both educational and entertaining. You'll see iconic landmarks and hidden gems, all dressed up for the holidays. It's a delightful way to experience the city's seasonal transformation, offering a glimpse into the heart of Chicago's holiday spirit.

New Year's Eve Fireworks at Navy Pier

The New Year's Eve fireworks at Navy Pier are a breathtaking display of light and sound that mark the culmination of the holiday season. As the clock ticks toward midnight, anticipation builds among the gathered crowds. Then, as the new year begins, the sky above Lake Michigan erupts in a symphony of color. The fireworks reflect off the water, creating a mesmerizing spectacle. It's a moment of celebration, reflection, and hope—a fitting end to the holiday season and a joyous welcome to the new year. Standing there, amidst the cheers and smiles, you feel a deep connection to the city and its people.

In Chicago, the holiday season is more than a series of events; it's a journey through a city imbued with warmth, creativity, and community spirit. Whether you're strolling through a market, gliding on ice, or watching the sky light up, you're part of a larger tapestry of holiday cheer. Chicago invites you to make lasting memories, to connect with others, and to savor the joyous spirit of the season.

*Prices fluctuate based on season and day of the week.

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