As the holiday season brightens the South Side of Chicago, the community comes alive with festive cheer, beloved traditions, and events that bring neighbors together.
The Chicago Southsider Holiday Event Guide is your ultimate resource for discovering the season’s best celebrations, from sparkling tree lightings to fun-filled family activities. Even better, many of these events are free and open to the public, ensuring everyone can join in the holiday magic. Plus, we’ve included a few citywide highlights to help you plan a season full of joy and connection!
ZooLights Presented by ComEd and Invesco QQQ
Date: Friday, Nov. 15 – Sunday, Jan. 5
Location: 2121 N Stockton Dr., Chicago, IL 60614
Cost: Varies – Buy Tickets here.
Lightscape – Chicago Botanic Garden
Date: Friday, Nov. 15 – Sunday, Jan. 5
Location: 1000 Lake Cook Road, Glencoe, IL 60022
Cost: Varies – Buy Tickets here.
Light of Christmas Drive Thru
Date: Thursday, Nov 21 – Sunday, Jan 5
Location: Guaranteed Rate Field, 333 W 35th St, Chicago, IL 60616
Cost: Varies – Buy Tickets here.
Millennium Park Holiday Art Market – Chase Promenade North
Date: Friday, Nov. 22 – Sunday, Nov. 24
Location: Milennium Park, Chase Promenade (North), Chicago, IL 60602
Cost: Free Admission
Learn more here.
The Wintrust Magnificent Mile Lights Festival
Date: Saturday, Nov. 23
Location: North Michigan Ave, Chicago, IL 60610
Cost: Free Admission
Learn more here.
90th Chicago Thanksgiving Parade
Date: Thursday, Nov. 28
Location: State Street, From Ida B. Wells Drive to Randolph Downtown Chicago
Cost: Free Admission
Learn more here.
Holiday Artisan Market – Navy Pier
Date: Friday, Nov. 29 – Sunday, Jan. 5
Location: Navy Pier, 600 E. Grand Ave Chicago, IL 60611
Cost: Varies – Buy Tickets here.
Christmas Vintage Festival – Water Tower Place
Date: Friday, Nov. 29 – Thursday, Dec. 12
Location: 835 N. Michigan Ave Suite 5060, Chicago, IL 60611
Cost: Free Admission
Learn more here.
Jack Frost Fulton Market
Date: Friday, Nov. 29 – Sunday, Jan. 5
Location: 170 N. Green St Chicago, IL 60642
Cost: Varies – Buy Tickets here.
Pre-Kwanzaa Holiday Celebration & Marketplace – Harris Park
Date: Friday, Dec. 6 & Saturday, Dec. 7
Location: 6200 South Drexel Ave, Chicago, IL 60637
Cost: Free Admission
Learn more here.
Catalog Holiday Marketplace – Willis Tower
Date: Tuesday, Dec. 10 – Wednesday Dec. 11 – Thursday, Dec. 12
Location: 233 S. Wacker Dr. Chicago, IL 60606
Cost: Free Admission
Learn more here.
Morgan Park Bevery Hills Holiday Markets
Date: Saturday, Dec. 7 & Saturday, Dec. 14
Location: 99th to 115th, Western Ave Chicago, IL 60612
Cost: Free Admission
Learn more here.
School & Studio Sale + Fundraiser at Hyde Park Art Center
Date: Saturday, Dec. 7 – Friday, Dec 22
Location: 5020 South Cornell Ave Chicago, IL 60615
Cost: Free Admission
Learn more here.
Youth Art Market – National Museum of Mexican Art
Date: Sunday, Dec. 8
Location: 1852 W. 19th St Chicago, IL 60608
Cost: Free Admission
Learn more here.
Black Joy Market at The Avenue
Date: Sunday, Dec 8
Location: 2916 South Wentworth Ave Chicago, IL 60616
Cost: Free Admission
Learn more here.
Randolph Street Holiday Market
Date: Saturday, Dec. 14 – Sunday, Dec. 15
Location: 1340 W Washington Chicago, IL 60607
Cost: Varies – Buy Tickets here.
Mercado de Intercambio: Holiday Market + Winter Clothes Swap
Date: Saturday, Dec. 14
Location: 4459 S Marshfield Ave Chicago, IL 60609
Cost: Free Admission
Learn more here.
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