Chicago’s holiday season brings cultural celebrations, live entertainment, family activities, festive markets and opportunities to support local businesses.
Whether you’re planning a family outing, shopping for gifts or exploring the city’s traditions, this guide highlights events and destinations to add to your calendar from Black-owned bookstores and African-inspired fashion boutiques to Kwanzaa celebrations and holiday performances.
2026 Holiday Events
November 2026
Black Harvest Film Festival
November 6–15 | Gene Siskel Film Center
Celebrate Black storytelling at the annual Black Harvest Film Festival, which showcases films by and about people of African descent. The festival provides a platform for filmmakers and stories exploring the Black experience.
Location: Gene Siskel Film Center, 164 N. State St., Chicago.
Christmas Around the World and Holidays of Light
November 7, 2026–January 3, 2027 | Griffin Museum of Science and Industry
Explore holiday traditions from around the world at the Griffin Museum of Science and Industry’s annual exhibition. The display features more than 50 decorated trees and cultural displays representing international celebrations, including Kwanzaa, Hanukkah and Diwali.
Location: Griffin Museum of Science and Industry, 5700 S. DuSable Lake Shore Drive, Chicago.
Africa Forum: November 2026
November 13 | 6:30–8:30 p.m.
Explore African American theater and drama with Cynthia CJ Maddox, Runako Jahi and India Nicole Burton. This hybrid discussion invites participants to engage with Black playwrights and theater.
Location: NEIU Carruthers Center for Inner City Studies, 700 E. Oakwood Blvd., Chicago.
Lightscape at Chicago Botanic Garden
November 13, 2026–January 3, 2027
Take a walk through an illuminated outdoor experience featuring colorful light installations, artistic displays and a signature light tunnel.
Location: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe.
W.O.W. Lit Fest – Words of Wonder Literary Festival
November 14 | 11 a.m.–6 p.m.
Celebrate literacy and storytelling at the Words of Wonder Literary Festival, highlighting Black authors and illustrators. Activities include storytelling, writing workshops, live music, African and Indigenous drumming, and book vendors.
Location: Dr. Conrad Worrill Track & Field Center, 10201 S. Cottage Grove Ave., Chicago.
ROOTED: An Art Exhibition Celebrating African and African American Culture
November 14 | 6–9 p.m.
Explore African and African American culture through art, music, food and community. ROOTED brings together visual artists and cultural experiences, including Nigerian cuisine.
Location: The Origin Restaurant & Lounge, 2010 W. Armitage Ave., Chicago.
Chicago’s Christmas Tree Lighting Ceremony
November 20 | 6 p.m.
Welcome the holiday season at the lighting of Chicago’s 113th annual Christmas tree in Millennium Park. The celebration includes live entertainment and fireworks.
Location: Millennium Park, near Michigan Avenue and Washington Street.
ZooLights at Lincoln Park Zoo
November 20, 2026–January 3, 2027
Experience millions of lights, seasonal displays, festive treats and family activities during Lincoln Park Zoo’s annual ZooLights celebration.
Location: Lincoln Park Zoo, 2001 N. Clark St., Chicago.
Wintrust Magnificent Mile Lights Festival
November 21 | Parade at 5:30 p.m.
Celebrate along Michigan Avenue with floats, giant balloons, musical performances and appearances by popular characters. Fireworks over the Chicago River follow the parade.
Location: Michigan Avenue, from Oak Street to Wacker Drive.
Chicago Thanksgiving Parade
November 26 | 7:45–10 a.m.
Bring the family downtown for floats, giant balloons, marching bands and cultural performers at the annual Thanksgiving Parade along State Street.
Location: State Street, from Ida B. Wells Drive to Randolph Street.
December 2026
100 Black Men of Chicago Annual Holiday Toy Drive
December 2 | 6–11 p.m.
Support a holiday tradition focused on giving back to children and families through the 100 Black Men of Chicago’s annual holiday toy drive. The event brings together community supporters for an evening of music, dancing and philanthropy.
Location: United Club at Soldier Field, 1410 Museum Campus Drive, Chicago.
TRC Community Marketplace: Holiday Edition
December 12 | 11 a.m.–4 p.m.
Support Black-owned businesses and local vendors at The Renaissance Collaborative’s holiday marketplace in Bronzeville. Shop for one-of-a-kind gifts, enjoy food from local vendors, and explore the historic former Wabash YMCA.
The building has an important place in Black history. In 1915, Carter G. Woodson founded the Association for the Study of Negro Life and History there, an organization that helped establish what became Black History Month.
Location: Historic Former Wabash YMCA, 3763 S. Wabash Ave., Chicago.
Chicago Tap Allstars: Winter Wonderland
December 12 | 1–3 p.m.
Celebrate Chicago’s tap dance tradition during Chicago Tap Allstars’ holiday production, Winter Wonderland. The performance features tap dancing, youth performers, and a celebration of the city’s rich dance history.
Location: Harold Washington Cultural Center, 4701 S. King Drive, Chicago.
The Other Cinderella – Black Ensemble Theater
December 12, 2026–January 24, 2027
Experience a fresh take on a familiar fairy tale with The Other Cinderella, an African American reimagining of the classic story. The Production brings music, humor, and cultural references to the stage.
Location: Black Ensemble Theater, 4450 N. Clark St., Chicago.
Malcolm X College Kwanzaa Celebration
December 26, 2026– January 1st 2027 | 10 a.m. – 6 p.m.
or over 20 years, Malcolm X College transforms its campus every single winter to host this event during the traditional holiday dates. Celebrate African American culture and community through a Kwanzaa gathering featuring cultural activities, food, music and opportunities to support local vendors.
Location: Malcolm X College 1900 W. Jackson Blvd, Chicago
SHOP CHICAGO: HOLIDAY GIFT GUIDE
This holiday season, consider shopping local and supporting Chicago’s Black-owned businesses, independent bookstores, African fashion boutiques and neighborhood retailers. From books and cultural gifts to jewelry, apparel, beauty products and home accessories, these stores offer options for different people on your holiday list.
Looking for the perfect gift for your friend who is the hostess with the mostest? Did your sister tell you she is doubling down on her wellness journal? Want to treat yourself with a new piece of jewelry, or better, want to personalize a charm you already love? Look no further.
The Villager shop, located in downtown Homewood, IL, has you covered. Their gift selection themes are taste, glow, and renew.
2007 Ridge Rd, Homewood, IL 60430
Remember the Maxine’s that once sat on 87th st, right off Stoney Island, IL? They’ve relocated to downtown Homewood, IL. This boutique is known for its jazzy fashions that appeal to Chicago’s more stylish, seasoned, and sophisticated women. They carry a variety of items, including shoes, accessories, coats, everyday clothing, and outfits and dresses for special occasions. Surprise your aunt with a Maxine’s gift card this holiday season.
Location: 1938 Ridge Rd, Homewood, IL 60430
Are you hosting the friendsmas this year? How about booking a candle-making class at the Mahogany Candle Shop in the heart of Homewood? When you visit their website, you will see firsthand what the class entails and how interesting a time it can be for you and your girls. In addition to the candle-making experience, this shop carries an array of candle sizes and scents, and regularly offers promotions, such as 15% off your first purchase. Book your candle-making experience today before all the slots are filled ahead of the holiday.
Location: 1941 Ridge Rd, Homewood, IL 60430
Call & Response Books I Hyde Park
A Black woman-owned independent bookstore focused on books by Black, Brown and Indigenous authors and other voices from the global majority. Shop for novels, nonfiction, poetry, children’s books and titles that encourage conversation and cultural discovery.
Location: 1390 E. Hyde Park Blvd., Chicago
Da Book Joint I South Shore
A Black mother-and-daughter-owned bookstore serving readers since 2007. Its selection includes books by established and emerging authors, African American history, children’s literature and books for personal growth.
Location: 6900 S. Stony Island Ave., Chicago
The Underground Bookstore I Calumet Heights
Find books focused on Black heritage, African and diaspora authors, history, spirituality, fiction and children’s literature. The bookstore also carries cultural items and educational resources.
Location: 1727 E. 87th St., Chicago
Honey & Hue Bookstore I Beverly
Shop for books from a Black-owned independent bookstore with a focus on inclusive storytelling and titles by Black authors. The store is a great option for children’s books, family gifts and readers looking for new voices.
Location: 1804 W. 103rd St., Chicago
Djenne Collection I Beverly
Shop African-inspired clothing, handmade fabrics, jewelry, handbags, accessories, shea butter and soaps. The store offers colorful textiles and gift options for shoppers interested in fashion and cultural goods.
Location: 1759 W. 95th St., Chicago
Kayra Imports I South Side and Hyde Park
Browse African clothing, Ankara print fabrics, jewelry, accessories, fragrance oils, African black soap and shea butter. Its selection offers options for fashion, beauty and culturally inspired gifts.
Chicago locations: 1643 E. 87th St.; 706 E. 83rd St.; and 1001 E. 53rd St.
Sage and Shea African Store I Bridgeport
Explore African clothing, accessories, fabrics, jewelry and beauty products. The shop offers options for shoppers looking for traditional and contemporary African-inspired fashion.
Location: 3502 S. Halsted St., Chicago
Sarah Kuenyefu Collection / House of Africa I Bronzeville
Shop fashion and accessories from designer Sarah Kuenyefu Searcy. The boutique offers women’s clothing, statement pieces, accessories and tailoring services.
Location: 4412 S. Cottage Grove Ave., Chicago
Thiocary Fashion I Woodlawn
Find African clothing for men and women, accessories, beauty products and lifestyle items at this family-owned fashion boutique.
Location: 6453 S. Cottage Grove Ave., Chicago
The Silver Room I Chicago
A Black-owned boutique and cultural destination offering jewelry, accessories, apparel, art, books and gifts. Its curated selection makes it a good stop for shoppers looking for creative pieces and gifts connected to Black culture and Chicago.
Location: 1506 E 53rd St, Chicago
Kilimanjaro International I Hyde Park
Shop African art, crafts, jewelry, clothing, cultural goods, incense, skincare and decorative items. The store is a good destination for shoppers looking for distinctive gifts and pieces inspired by African culture.
Location: 1305 E. 53rd St., Chicago
Absolutely Anything Essential I Bronzeville
Explore a multi-level gift shop and small-business incubator featuring gifts, wellness products, locally sourced items and creative goods. A useful stop for shoppers who want to discover independent makers and small businesses.
Location: 3521 S. King Drive, Chicago
Chicago Fair Trade Holiday Pop-Up Shop
November 1–December 23
Shop a curated collection of fair-trade and eco-friendly gifts from more than two dozen local businesses. Products include jewelry, fashion, home décor, toys, gourmet treats, chocolate and coffee.
Location: 2717 N. Clark St., Chicago
Randolph Street Holiday Market
November 14–15 and December 12–13
Browse vintage finds, art, antiques, jewelry, clothing, home décor and handcrafted gifts from independent vendors.
Location: 1340 W. Randolph St., Chicago
One of a Kind Holiday Show I December 3–6
Shop handmade gifts from hundreds of artists, designers and makers, with products ranging from jewelry and accessories to ceramics, clothing, gourmet goods and home décor.
Location: The Mart, 222 W. Merchandise Mart Plaza, Chicago
Millennium Park Holiday Market I November 20–22
Shop seasonal gifts, enjoy live entertainment and explore downtown holiday festivities during the Millennium Park Holiday Market.
Location: Millennium Park, Chicago
Chicago’s holiday season is a time for food, family, gift-giving, festive decorations, and cherished traditions. It’s also an opportunity to support local entrepreneurs, celebrate culture, discover new artists and authors, and create lasting memories with family and friends.
From Black-owned bookstores and fashion boutiques to community marketplaces, cultural exhibitions and Kwanzaa celebrations, there are countless ways to support the people and organizations that make Chicago special.
Wishing you and your loved ones a happy, safe, and wonderful holiday season!
From all of us at The Chicago Defender.
