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Five Things To Do in Chicago: Nov. 21–23, 2025
Winter is easing in, and with it comes a new lineup of reasons to brave the cold. Here are a few standout events worth bundling up for this weekend.
Ring in the season at the Tree Lighting Ceremony.
Chicago's annual Tree Lighting Ceremony returns to Millennium Park, marking the start of the holiday season with the illumination of the city's official Christmas tree. The event features multiple viewing areas, festive food options, and a main stage along Washington Street where guests can take in live entertainment before the lighting of the tree.
Date: Nov. 21
Time: 5–7 p.m.
Cost: Free
Location: Millennium Park, 201 E. Randolph St.
More Info: chicago.gov
Discover handmade goods at Mercadito.
Mercadito brings together local artisans, small businesses, and neighborhood makers for a community-centered shopping experience. Visitors can browse handcrafted goods ranging from jewelry and artwork to home décor, baked items, and personal accessories, with each vendor representing the creativity and cultural traditions of Rogers Park. This year's event includes free gift wrapping (donations welcome) and complimentary ponche while supplies last.
Date: Nov. 22
Time: 10 a.m.–3 p.m.
Cost: Free
Location: GROW/PROGRESANDO, 7056 N. Clark St.
More Info: business.rpba.org
Watch the magic of the Wintrust Magnificent Mile Lights Festival.
The Wintrust Magnificent Mile Lights Festival brings its signature blend of parade spectacle and holiday cheer to Michigan Avenue. The nighttime procession features illuminated floats, marching bands, and special appearances from Mickey Mouse, Minnie Mouse, and other familiar characters from Walt Disney World Resort. More than a million lights brighten the surrounding trees, creating one of the city's most recognizable seasonal displays.
Date: Nov. 22
Time: 11 a.m.–7 p.m.
Cost: Free
Location: Pioneer Court, 625 N. Michigan Ave.
More Info: themagnificentmile.com
Support your local filmmaker at the Film Workers' Holiday Market.
The Film Workers' Holiday Market highlights local makers connected to Chicago's film community, offering a varied selection of handcrafted goods, artwork, and creative items. The market provides space for behind-the-scenes industry professionals, like designers, crafters, and visual artists, to share their work in one place. Visitors can browse unique gifts, support independent creators, and meet members of the city's production scene. The event functions as both a festive shopping opportunity and a look into the creative talent that contributes to Chicago's film ecosystem.
Date: Nov. 22
Time: 12–5 p.m.
Cost: Free
Location: CineCity Studios, 2429 W. 14th St.
More Info: facebook.com
Explore tradition at JASC Holiday Delight & Komodo Matsuri.
This event offers a full day of cultural programming, artisan shopping, and family-friendly activities rooted in Japanese American traditions. Visitors can explore vendor booths featuring handcrafted goods, enjoy performances highlighting music and dance, and sample food prepared by community partners. The event blends holiday celebration with cultural heritage, creating an accessible environment for longtime supporters and first-time attendees alike.
Date: Nov. 22
Time: 10 a.m.–4 p.m.
Cost: Free
Location: Japanese American Service Committee (JASC), 5700 N. Lincoln Ave.
More Info: jasc-chicago.org
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