The holidays in Chicago are the gift that keeps on giving. For generations, visitors have gathered each winter for festive parades, cherished annual traditions, and glittering spectacles across the city.
Like a holiday storybook come to life, winter in Chicago turns ordinary moments into joyful celebrations. Join the fun and embrace the season’s magic that makes Chicago feel warm and bright, even on the chilliest days.
Chicago holiday celebrations
At a glance: top holiday activities in Chicago
Looking for things to do this holiday season in Chicago? You can admire twinkling light displays at Lincoln Park Zoo and beyond, go ice skating with skyline views in Millennium Park, see the city’s grand Christmas tree, shop for gifts at charming holiday markets like the annual Christkindlmarket, catch a holiday show in a stunning downtown theatre, hop on the CTA holiday train, plan a festive Christmas dinner, and so much more.
Catch a festive holiday parade
Each winter, holiday parades sweep through the streets of Chicago in a swirl of color, glittering lights, and the magic of the season.
The Wintrust Magnificent Mile Lights Festival
Saturday, Nov. 22, 2025
This family-friendly evening parade officially kicks off the holiday season in Chicago. As night falls, Michigan Avenue glows with more than a million lights during the grand tree‑lighting parade, featuring beloved Disney characters, marching bands, colorful floats, giant balloons, musical sets, and more. Cap off the festivities with an enchanting fireworks show over the Chicago River.
Chicago Thanksgiving Parade
Thursday, Nov. 27, 2025
A true feast for the senses, the Chicago Thanksgiving Parade has delighted generations of spectators for more than 90 years. Watch Chicago’s iconic State Street come alive with fully decked-out floats and larger-than-life balloons while spirited performers and marching bands spread holiday cheer.
Be dazzled by sparkling Christmas lights
Between luminous walking trails and brilliant light shows, the city shines brightest during the holiday season. Discover the most captivating Christmas light displays in Chicago.
ZooLights at Lincoln Park Zoo
Nov. 21, 2025 – Jan. 4, 2026
Illuminating the zoo with over three million lights and hundreds of festive LED displays, ZooLights returns with more sparkle than ever. Look forward to a flurry of seasonal attractions, such as live ice carving, festive carolers, the bilingual Zooltide light show, and cozy holiday treats like hot cocoa, mulled wine, and s’mores by the fire.
Lightscape at Chicago Botanic Garden
Nov. 14, 2025 – Jan. 4, 2026
Experience the Chicago Botanic Garden in a whole new light — after dark. A stone’s throw from Chicago, this immersive holiday event invites you to wander through a 1.3-mile dreamscape of colorful lights and artistry. For kid-friendly fun, Jingle Jam Family Nights offers meet and greets with Santa, Mrs. Claus, the Snow Queen, and other characters, plus festive bites and a lively dance party.
Illumination: Tree Lights at the Morton Arboretum
Nov. 15, 2025 – Jan. 3, 2026
Make your way through a radiant one-mile trail brimming with creative light displays, playful shadow art, and this season’s newest crowd‑pleaser: four vibrant animal sculptures from the Vivid Creatures exhibition. Special highlights include Electric Illumination — an adults-only party featuring a live DJ — and dog admission nights, where visitors can bring along their fluffy companions.
Explore more: Check out all our favorite spots to see Christmas lights in Chicago.
Explore charming holiday markets
Amid twinkling lights and bustling stalls, Chicago’s holiday markets place the spotlight on one-of-a-kind gifts and experiences. Find treasures big and small at these festive pop-up markets.
Christkindlmarket Chicago
Nov. 21 – Dec. 24, 2025
Each winter, Christkindlmarket Chicago turns the city’s center into an enchanted wonderland of Old World charm. Wooden stalls overflow with artisanal crafts, holiday music drifts through the air, and lights twinkle against a skyline backdrop. Add in the irresistible aroma of fresh pretzels, bratwurst, roasted nuts, and soul-warming glühwein (mulled wine), and you’ve stepped into a holiday fairytale.
Christkindlmarket Wrigleyville
Nov. 23 – Dec. 31, 2025
Nestled beside historic Wrigley Field, Christkindlmarket Wrigleyville creates a pocket of holiday magic in a welcoming neighborhood setting. At this free outdoor market, visitors can browse handcrafted ornaments, toys, and gifts while savoring European-inspired food and drink.
@choosechicagoIt’s almost time! @thechristkindlmarket opens 11/21! Here’s a quick guide to the sips and eats at Chicago’s beloved free outdoor German-style holiday market. 📍 Daley Plaza 📅 11/21-12/24 🔗 Tap the link below for more info! https://www.choosechicago.com/blog/dining/what-to-eat-and-drink-at-christkindlmarket/ #NeverOutdoneChi♬ original sound – Choose Chicago
Chicago’s holiday shopping scene extends far beyond Christkindlmarket. The One of a Kind Holiday Show fills its halls with local artisans and handmade wares, Randolph Street Market is a vintage shopper’s dream, and the Africa International House’s Pre-Kwanzaa Celebration & Marketplace honors culture and community.
Explore more: Shop for gifts at the top Chicago holiday markets.
Head to the theatre for a festive holiday show
Embrace the holiday spirit with an impressive lineup of live shows and productions — musicals, improv, ballet, plays, and more. Whether you’re in the mood for elegance, laughter, or heartwarming stories, Chicago’s stages deliver it all this season.
Book your tickets today for these must-see holiday shows in Chicago:
- A Christmas Carol at the Goodman Theatre (Nov. 15 – Dec. 31, 2025)
- The Nutcracker by Joffrey Ballet at the Lyric Opera House (Dec. 5 – 28, 2025)
- The Art Deco Nutcracker by the A&A Ballet at The Athenaeum Theatre (Dec. 6, 2025)
- It’s A Wonderful Life: A Live Radio Playat The Athenaeum Theatre (Dec. 12 – 31, 2025)
- Rudolph Runs Wild at The Second City (Nov. 30 – Dec. 31, 2025)
- Charles Dickens Begrudgingly Performs a Christmas Carol Again at Theater Wit (Dec. 4 – 28, 2025)
- Hershel and the Hanukkah Goblins at Raven Theatre (Nov. 29 – Dec. 28, 2025)
Take a spin on the ice
Trade your boots for skates and glide across one of Chicago’s scenic ice skating rinks. Few holiday traditions feel as timeless — or magical — as skating beneath the shimmering skyline at Millennium Park on a frosty winter night.
McCormick Tribune Ice Rink at Millennium Park
Nov. 21, 2025 – Feb. 1, 2026
Take in postcard‑perfect scenery with every lap at this iconic downtown ice rink next to Cloud Gate (known as “The Bean”). Visitors can make reservations online, rent skates on site, and even take advantage of free weekend skating lessons available for all ages.
Maggie Daley Park Skating Ribbon
Nov. 14, 2025 – March 8, 2026
Unlike a traditional rink, the Skating Ribbon winds gently through the park, so skating feels like journeying through a wintry landscape. At about a quarter‑mile long, the rink has slight inclines and declines that let you pick up speed naturally. Plan ahead and reserve your spot today.
Outside the Loop, you can skate your way through the season at neighborhood rinks, such as the Gallagher Ice Rink in Wrigleyville and Midway Plaisance in Hyde Park.
See the Chicago Christmas Tree
For more than a century, the City of Chicago Christmas Tree has served as the centerpiece of the city’s holiday festivities. Every November, visitors gather at Millennium Park to watch the unveiling of the massive spruce.
The annual Tree Lighting Ceremony kicks off with live performances, from local talent to youth choirs, creating a festive atmosphere that builds toward the big countdown. As the tree illuminates, colorful fireworks soar above the nearby Chicago Cultural Center.
Shining brightly on Michigan Avenue and Washington Street through early January, the city’s official Christmas tree is a must‑see on any holiday outing in Chicago.
Experience festive fun at a museum
During the winter, the holidays are in full swing at Chicago’s most popular museums. At the Art Institute of Chicago, the iconic stone lions are wreathed in massive evergreens each winter. Inside, the Neapolitan Crèche is a spectacular 18th-century nativity scene that will be on display through Jan. 5, 2026.
Likewise, the Griffin Museum of Science and Industry gets into the spirit of the season with its Christmas Around the World and Holidays of Light exhibit. Stand in awe of more than 50 festive trees, each adorned with culturally inspired decorations to reflect holiday customs from every corner of the world.
Find the perfect gifts while holiday shopping in Chicago
Stretching along Michigan Avenue, The Magnificent Mile becomes even more magical during the holiday season. Take advantage of exclusive deals and seasonal surprises at flagship stores, world-class retailers, specialty shops, and luxury showrooms lining the avenue. Discover thoughtful gifts while admiring dazzling lights and holiday decor.
Known for its historic department stores and bustling energy, State Street is an essential Chicago shopping destination. In the winter, storefront windows sparkle with elaborate displays, and shops offer curated seasonal collections. There’s no shortage of timeless gifts and trendy finds at this centrally located retail district.
For chic boutiques, artisan markets, and vintage shops, head to Chicago’s neighborhoods for unique holiday shopping. Areas like Andersonville, Hyde Park, and Lincoln Park are home to small businesses that specialize in one‑of‑a‑kind finds, from handcrafted jewelry and home decor to locally designed fashion.
Explore more: Let our guide to holiday shopping in Chicago lead you to the perfect gifts.
Savor the season with a special holiday meal
Experience peak holiday magic at the legendary Walnut Room. Tucked inside Macy’s on State Street, this timeless restaurant — the country’s first-ever department store dining room — has remained a cherished holiday landmark for generations.
The towering Great Tree is the establishment’s centerpiece, framed by chandeliers and elegant decor that set the stage for an unforgettable holiday meal. The menu carries its own history, too — Mrs. Hering’s chicken pot pie, which stays faithful to the original recipe from 1890, is a notable favorite.
Beyond the restaurant, Macy’s iconic holiday windows transform the building’s exterior into a charming seasonal display that attracts crowds year after year. Inside and out, Macy’s captures the spirit of the season, bringing joy to passersby of all ages.
Explore the top restaurants in Chicago for a festive meal, including places to enjoy holiday tea and exceptional Christmas and Hanukkah dinners.
Spot the Chicago holiday train
For over 30 years, the CTA Holiday Train has delighted thousands of riders every winter. Running on all rail lines from late November to late December, the train features six rail cars covered in glittering lights and ornaments, plus a flatcar carrying Santa’s sleigh.
At the front of the train, Santa waves from his sleigh while elves greet passengers with candy canes. And on the streets, the festive Holiday Bus brings cheer to Chicago neighborhoods with merry tunes and Santa’s jolly spirit.
