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Last updated: November 11, 2024

Plan your holiday adventure in Chicago Loop with our comprehensive event guide. Whether you're rediscovering Chicago Loop or falling in love with it for the first time, our guide maximizes your festive experience.

One highlight of the season is the Christkindlmarket, a charming German-style Christmas market where you can explore festive stalls offering handmade ornaments, delicious treats, and warm drinks. Another must-see event features the dazzling holiday lights along Michigan Avenue as part of the Magnificent Mile Lights Festival, transforming the city into a twinkling winter wonderland. And the Christmas Tree Lighting at Millennium Park is something you definitely don't want to miss, showcasing a stunning tree accompanied by delightful holiday music. See more details on these and other fun events and activities below!

Contact information and details below.

Chicago Loop Holiday Light Displays

What to Expect:

Largest nighttime parade in the U.S. with one million lights and festive activities.

Description:

The Wintrust Magnificent Mile Lights Festival is a day-through-night holiday extravaganza featuring a spectacular parade down North Michigan Avenue with Mickey Mouse and Minnie Mouse, giant helium balloons, marching bands, and musical performances. The event culminates with the Wintrust Fireworks Spectacular over the Chicago River, illuminating over 200 trees with one million lights.

Where: Chicago | More Info: Magnificent Mile Lights Festival

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What to Expect:

Interactive light displays synchronized to music in a fully ADA-compliant environment.

Description:

Explore 50 acres of the Morton Arboretum's majestic trees during this spectacular light, sound, and color display. The 2024 exhibition features 17 displays, including a secluded glade with fairy lights and kinetic LED tall grasses honoring Midwest native species. Celebration Circle is a new interactive light display in the Gerard T. Donnelly Grand Garden, featuring four sets of illuminated tree-shaped installations synced to different instruments.

Where: Lisle | More Info: Illumination: Tree Lights at The Morton Arboretum

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What to Expect:

Holiday celebration with synchronized light and animal displays.

Description:

Brookfield Zoo's Holiday Magic features over two million twinkling LED lights, giant illuminated animals, and immersive lighting areas like Candy Cane Lane and Sparkling Coast. Enjoy unique shopping at the Holiday Market, seasonal food and beverages, and explore indoor and outdoor animal habitats.

Where: Brookfield | More Info: Holiday Magic at Brookfield Zoo

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What to Expect:

Dazzling outdoor light displays and ice-skating rink.

Description:

Light Up the Lake at Navy Pier features dazzling outdoor lakefront light displays, an outdoor ice-skating rink, cozy firepits, and the heated Centennial Ferris Wheel. Enjoy live music and artisan markets while experiencing the thrill of axe throwing.

Where: Chicago | More Info: Light up the Lake at Navy Pier

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Chicago Loop Holiday Markets and Shopping

What to Expect:

Traditional German holiday market with over 50 vendors and festive events.

Description:

Christkindlmarket is a German-style Christmas market offering free admission, featuring international and local vendors, unique shopping, festive live entertainment, and a variety of international and local foods.

Where: Chicago | More Info: Christkindlmarket

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What to Expect:

Celebrating local craftsmanship with over 400 artisans.

Description:

Renegade Craft Fair is a premier event showcasing over 400 local and national artisans, designers, and makers. The fair features a diverse array of handmade goods, from jewelry and pottery to candles and screenprints. It is held in various locations around Chicago, including Wicker Park and Andersonville, and offers a unique shopping experience that supports local small businesses.

Where: Chicago | More Info: Renegade Craft Fair

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Chicago Loop Holiday Shows and Entertainment

What to Expect:

World-class ballet performance inspired by Chicago's 1893 World's Fair.

Description:

The Joffrey Ballet's production of The Nutcracker is a holiday tradition set in Chicago's 1893 World's Fair. Choreographed by Christopher Wheeldon, it features a celebrated creative team and Tchaikovsky's classic score. The story follows Marie and her mother as they experience a festive celebration and a whirlwind journey with the Nutcracker Prince.

Where: Chicago | More Info: The Nutcracker by Joffrey Ballet

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What to Expect:

Longest-running consecutive holiday tour in the entertainment industry.

Description:

Mannheim Steamroller is a renowned musical ensemble known for their unique blend of 18th-century classical rock and New Age music. With over 41 million albums sold, they have become the #1 Christmas music artist of all time, performing in numerous countries and creating a distinctive sound that has transformed holiday music.

Where: Chicago | More Info: Mannheim Steamroller

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What to Expect:

Whimsical adaptation of Dr. Seuss' classic with magnificent sets and costumes.

Description:

Dr. Seuss' How the Grinch Stole Christmas The Musical is a heart-warming holiday classic featuring hit songs "You're A Mean One, Mr. Grinch" and "Welcome Christmas." Max the Dog narrates as the mean and scheming Grinch, whose heart is "two sizes too small," decides to steal Christmas away from the holiday-loving Whos. This production is praised for its extraordinary performance, bright and tuneful music, and delightful entertainment for both kids and adults.

Where: Chicago | More Info: How the Grinch Stole Christmas

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What to Expect:

Innovative digital graffiti and hip-hop dance blend with Tchaikovsky's music.

Description:

The Hip Hop Nutcracker is a contemporary dance spectacle that re-mixes and re-imagines the classic Nutcracker story with hip-hop dance and Tchaikovsky's timeless music. Directed and choreographed by Tony and Olivier Award-nominated Jennifer Weber, this holiday event features a powerhouse cast of all-star dancers, a DJ, a violinist, and MC Kurtis Blow. The show transforms E.T.A. Hoffmann's beloved story from traditional 19th Century Germany to vibrant, diverse contemporary New York City.

Where: Chicago | More Info: Hip Hop Nutcracker

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What to Expect:

Legendary vocalists performing Motown classics and holiday favorites.

Description:

Celebrate the holidays with iconic vocalists from Ali Woodson’s Temptations, The Miracles, and The Contours, backed by a 6-piece band. Enjoy soulful renditions of Motown classics and festive favorites, complete with dazzling choreography and unforgettable harmonies.

Where: Chicago | More Info: A Motown Christmas

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What to Expect:

Live orchestral performance of John Williams' iconic score.

Description:

The Chicago Symphony Orchestra performs John Williams' delightful, Academy Award-nominated score from the 1990 comedy classic "Home Alone." Relive the hilarious and heartwarming tale of 8-year-old Kevin McCallister defending his home against bumbling burglars. The live concert features special preconcert dining options and a free preconcert conversation with conductor Richard Kaufman and actor Tracy Connor.

Where: Chicago | More Info: Home Alone in Concert by Chicago Symphony Orchestra

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What to Expect:

Legendary singer performing iconic holiday hits and romantic ballads.

Description:

Join legendary singer Johnny Mathis for a two-hour Christmas concert featuring his iconic holiday hits and romantic ballads. Experience his timeless voice and classic songs that have captivated generations of fans.

Where: Chicago | More Info: Johnny Mathis Christmas Concert

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Chicago Loop Other Holiday Activities

What to Expect:

Free ice skating with beginner and intermediate lessons.

Description:

Ice skating at Millennium Park features a free, open-air rink with stunning views of Chicago's skyline. Free skating lessons are available for beginners and intermediate skaters, made possible by the McDonald's Active Lifestyles Endowment managed by the Millennium Park Foundation. Snacks and hot drinks are available from Momentum Coffee and Millennium Hall.

Where: Chicago | More Info: Ice Skating at Millennium Park

Event Organizer?

What to Expect:

Unique celebration of global holiday traditions with over 50 decorated trees.

Description:

Explore rich holiday traditions from around the globe at the Museum of Science and Industry. The event features a four-story, floor-to-dome Grand Tree surrounded by more than 50 trees and displays decorated by volunteers to represent holiday traditions from cultures worldwide.

Where: Chicago | More Info: Christmas Around the World at the Museum of Science and Industry

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What to Expect:

Interactive holiday activities with international cuisine and private event spaces.

Description:

Winterland at Gallagher Way offers a variety of rides, games, and family-friendly activities, including ice skating and festive food options. The event features international cuisine, holiday markets, and unique private event spaces like the Maker's Mark Chalet and U.S. Virgin Islands Igloo Experience.

Where: Chicago | More Info: Winterland at Gallagher Way

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What to Expect:

Holiday-themed 5K with festive swag and charity support.

Description:

The Santa Hustle Chicago is a festive 5K and Kids Dash event at Navy Pier, offering participants a long sleeve ugly sweater, Santa Hustle embroidered beanie, and finisher medal. The event supports Cal's Angels, a pediatric cancer foundation, and includes various holiday-themed swag and activities.

Where: Chicago | More Info: Santa Hustle

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What to Expect:

Celebrating 40 years of fundraising for arthritis research.

Description:

The Chicago Jingle Bell Run is a festive charity event where participants wear holiday gear to support the Arthritis Foundation. It marks the 40th year of the original festive race, funding critical research and treatments for arthritis.

Where: Chicago | More Info: Chicago Jingle Bell Run

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