Enclosed see through igloo in the Chicago winter

December 12th – 15th: Fun Things to do in Chicago this Weekend

This weekend, continue to count down to the holidays with this guide filled will holiday-themed marketplaces. Instagram-worthy pop-up bars, and cultural celebrations that will continue to make your season bright.


Sincerely, Ritchurd Presents: The Warmest Winter

Saturday | December 14th | 4:30 p.m.

PERSONA | 408 South Wells St. | $20 – $250

This December, the fashion scene in Chicago gets a little warmer. Sincerely, Richard hosts its third annual winter fashion showcase at Persona Lounge in the Chicago Loop. The evening features an exclusive sneak peek of 2020 spring and summer collections from some of the coldest designers in fashion today. In partnership with Iyanu Foundation, the Sincerely, Richurd will accept winter wear to make someone else winter that much warmer in Chicago. For tickets to this unique fashion showcase, visit the event page here. 

Vends + Vibes 2019: An Arts Marketplace

Saturday and Sunday | December 14th – 15th | 12:00 p.m. – 5:00 p.m.

Arts Incubator |The historic 300 East Block of Garfield Boulevard in Washington Park | Free

Make holiday shopping local and easy at 6th Annual Vends + Vibes. This two-day winter marketplace is filled with unique handmade products made primarily by over 30 South Side artists and creative entrepreneurs. Join the Arts Block community in Washington Park to discover one-of-a-kind holiday gifts as you take in soulful vibes from some of Chicago’s hottest DJs and partake in family-friendly fun including art-making activities, marshmallow roasting, photos with Santa and more. For details and a list of participating vendors, visit the website here.

Food + Drink: 

Jack Frost Winter Village

Saturday | December 14th | 12:00 p.m. – 7:00 p.m.

Jack Frost’s Winter Village Pop-Up & Christmas Tree Farm | 455 N. Elston Ave. | $0 – $112

Chicago’s largest holiday pop-up takes over the Goose Island neighborhood this weekend. Jack Frost Winter Village is a Chicago winter-long destination that is perfect for all ages. The festive pop-up experience features food trucks, wintery drinks, ice skating & bumper cars, carolers, a Christmas farm, and much more. For tickets and additional details to this event, visit the website here.

Chicago Vegan Test Kitchen: 2 Year Anniversary Holiday Market

Sunday | December 15th | 11:00 a.m. – 4:00 p.m.

Emporium Logan Square | 2363 N Milwaukee Ave. | Free

Stop by Logan Square this weekend for the Chicago Vegan Test Kitchen’s food-focused holiday market. Chicago Vegan Test Kitchen is a community of local, plant-based chefs, cruelty free crafters, vegan body care and wellness vendors. Indulge in all the Vegan treats from conscious local chefs while shopping for cruelty free goods. For more details, visit the event page.


Caroling at the Youth Detention Center

Friday | December 13th | 6:00 p.m. – 7:30 p.m.

The Juvenile Temporary Detention Center | 1100 S Hamilton Ave. | Free

Image | Mom’s Against Violence and Incarceration

Join grass-root community organizations this weekend to uplift Chicago’s incarcerated youth with holiday songs and positive light. Show love to the youth at the Cook County Juvenile Detention Center and spread cheer to others who need it this year. For more details, visit the event page.

Arts + Culture:

Pre-Kwanzaa Marketplace

Friday – Saturday | December 13th – 14th | Time Varies

Africa International House | 6200 S Drexel Ave. | Free

Experience a rich art and culture Pre-Kwanzaa Holiday Marketplace at the Africa International House this December in Chicago. Witness the sights, sounds, smells, and the passion of a proud people with a long-standing history. Shop with creative and inventive vendors, taste delectable indigenous dishes; feel and wrap yourself in wearable arts that set you apart in unique styling. Revel in the vitality of this fun-filled celebration for families and communities. For more details on this event, visit the event page here. 

Sam Trump’s Nat Cole Tribute w/ Wind Orchestra

Sunday | December 15th | 6:00 p.m. – 9:00 p.m.

Untitled Supper Club| 111 W Kinzie St. | Free

Experience the music of one of Chicago’s most infamous musicians, Nat King Cole this weekend at Untitled Supper Club in Chicago. The free all-ages show will feature two highly revered Nat ‘King’ Cole albums and Christmas songs. Local musician Sam Trump will cover the music of Nat King Cole. He will be accompanied by an 18-Piece Wind Orchestra (Clarinet, Tuba, Flute, Trumpet, etc.) complete with a Harp, and a rhythm section made of Upright Bass, Drum Set, and Piano. For the full show, details are sure to visit the event page here.

Find the best things to do this November by checking out this month’s events guide. Need more ideas on this go do? Check out 32 of the best fall events happening in Chicago.

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