Christmas Tree on 400 Michigan Avenue in Chicago as featured on The Haute Seeker

Chicago Event Guide December 2019

Can you believe it? This is my last Chicago event guide for 2019. Not just that, but that last event guide for this DECADE! This month, I want to end the year with an event guide that is sure to keep you busy all December long. From local holiday markets to unique arts and cultural events, this is guide has everything you need to make the last month of the year, the best one yet.


One of a Kind Holiday Show

Thursday – Sunday | December 5th – 8th | 2:00 p.m. – 6:00 p.m.

Merchandise Mart | 222 West Merchandise Mart Plaza | $12 – $20

The One of a Kind Show, held two times per year, features handmade items from hundreds of makers. Enjoy a one-of-a-kind experience with great food and entertainment while you shop. More than 600 independent makers will set up shop at as shoppers browse a variety of categories of handmade work. You can check out the goods in person, ask questions, and find just about anything you could want — jewelry, home goods, clothes, art, and more. Find one-of-a-kind gifts for friends and family (or yourself) and support artists and makers. Grab tickets, using my special link, and save on tickets to the One of a Kind Show here. 

12 Days of Charity

Wednesday | December 11th | 5:00 p.m. – 8:00 p.m.

SX Sky Bar | 808 South Michigan Ave. | Free

Give back fashionably this December in Chicago with SX Sky Bar’s 12 Days of Charity. Peruse a visual display of fashion through the decades, courtesy of Columbia College Chicago’s Fashion Studies Collection, benefiting Dress for Success. Enjoy style while enjoying holiday food and drink specials. Guests who donate clothing will receive a makeup touch-up and professional headshot. For more details on this event and a list of more significant needed items, visit the event page here. 

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. 

Holiday Craft Show

Sunday | December 8th| 12:00 p.m. – 5:00 p.m.

Metropolitan Brewing | 3057 N Rockwell St | Free

Check out over 20 local artisans at one of Chicago’s best breweries. Metropolitan Brewing in West Lakeview hosts a market featuring local artists and makers. Grab a beer and do some holiday shopping at this Northside microbrewery. For a full list of participating vendors, visit the website here. 

Food + Drink:

National Coquito Festival

Thursday | December 5th | 6:00 p.m. – 9:00 p.m.

Puerto Rican Arts Alliance | 3000 N. Elbridge| $65

Keep the festivities of the holiday season at the National Coquito Festival. Coquito is a traditional Christmas drink that originated in Puerto Rico. It is a coconut-based alcoholic beverage that is similar to eggnog. Sip a variety of coquitos, enjoying parranda live music, great Puerto Rican food, and complimentary raffle prizes for our guests. Sample this festive drink with friends and family this December in Chicago. For tickets to the event, visit the website here. 

Chicago Wine Fest: Winter Edition

Saturday | December 7th | 5:30pm – 10:00pm

Artifact Events | 4325 N Ravenswood Ave. | $60

Get a little naughty or nice at Wine Fest this month. Celebrate the holiday season with the best-elevated wine tasting experience that aims to stimulate all of your senses. Bring your friends, or just yourself, and drink your day away with specially curated wineries or sample premium wine to your heart’s content while live entertainment keeps the party lively during this one of a kind wine experience. Get discounted general admission tickets(thanks to your girl) or VIP tickets here.

Happy’s: A Holiday Pop-Up Bar

Sunday – Saturday | December 2nd – 28th | 5:00 p.m. – 10:00 p.m.

Chicago Athletic Association Hotel  | 12 S Michigan Ave. | Price Varies

Image | Chicago Athletic Association Hotel

Experience a unique pop-up bar experience this December in Chicago at the Chicago Athletic Association Hotel. Happy’s – Chicago Athletic Association Hotel‘s annual holiday pop-up bar – is back, and this season it’s bigger, brighter, and comes bearing bar snacks. Warm-up with liquid cheer crafted by Land and Sea Dept., and get in the spirit by participating in holiday programming throughout the month. For a full list of daily events and programs at Happy’s, visit the Facebook page.

BrewLights at Lincoln Park Zoo – Presented by Louis Glunz Beer, Inc.

Thursday | December 12th | 5:30 p.m. – 9:30 p.m.

Lincoln Park Zoo| 2234 North Cannon St | $20 – $49

Brews, tigers, bears—oh my! BrewLights, presented by Louis Glunz Beer, Inc. and hosted by the Auxiliary Board of Lincoln Park Zoo, features craft and seasonal beers on tap throughout the zoo. Guests at the festive beer-tasting event will sip and savor specialty brews while supporting Lincoln Park Zoo under the beautiful holiday lights. The evening also includes opportunities for photos with Santa at the Helen Brach Primate House, free rides on the AT&T Endangered Species Carousel, and more. For tickets to Brewlights, be sure to visit the event page.


MLK Kickoff Event and Tree Lighting Ceremony at Cole Park

Sunday| December 1st | 1::00 p.m. – 5:00 p.m.

Nat King Cole Park | 8502 S. King Dr. | Free

Be a light to the South Side neighborhoods this winter in Chicago. This December, serve alongside other My Block, My Hood, My City volunteers in the Chatham neighborhood of Chicago as you bring holiday cheer to under-resourced communities. The first-holiday lighting event is consisting of home decorations, a toy drive, food vendors, holiday music, and more. To volunteer, visit the website here. 

FIRSTHAND-Gun Violence: Screening and Discussion

Wednesday | December 4th | 6:00 p.m. – 7:30 p.m.

Venue 610 | 610 S Michigan Ave. | $10

Gun Violence in Chicago is a topic of heartbreak and constant conversation. Join WTTW this month, in partnership with Leadership Greater Chicago, to watch selections from the documentary series FIRSTHAND: Gun Violence and discuss the critical issue of gun violence in Chicago from different perspectives. WTTW News and Chicago Tonight Correspondent Brandis Friedman will moderate a discussion with two participants from FIRSTHAND – READI Chicago outreach worker Reality Allah and Community Policing Sergeant in the Austin 15th District Jermaine Harris – as well as WTTW producer/director Dan Protess and WTTW | WFMT President & CEO Sandra Cordova Micek. For tickets to the event, visit the website here. 

2019 Chicagoland Toy Drive

Tuesday | December 10th | 5:00 p.m.

Godfrey Hotel| 127 W Huron St. | Free

Give back this month in Chicago with ChiGivesBack, Inc. during their 2019 Chicagoland Toy Drive. The annual event has one goal—to bring a smile to the children and families who might not otherwise receive toys during the holiday season. This event will include a DJ, live music, silent auction, raffles, and giveaways throughout the evening. If you’d like more information, please visit

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. 

A Very Merry Christmas Concert

Sunday | December 22nd | 7:00 p.m. – 9:00 p.m.

National Museum of Mexican Art | 1852 West 19th Street | $25

Celebrate the holidays with a special Christmas Concert featuring the Mariachi Herencia de Mexico. he Latin GRAMMY-nominated group performs Mexican and American holiday favorites, including ”Feliz Navidad,” “Los Peces en el Rio,” “Sleigh Ride,” “Mi Burrito Sabanero,” “Jingle Bells”, “O Holy Night”, “The Chipmunk Song (Christmas Don’t Be Late),” and much more! Filled with music and dance, this colorful celebration of Mexican holiday traditions is perfect for the whole family. For tickets, visit the event page here.

WGCI Big Jam 2019

Friday | December 20th | 7:00 p.m. – 11:00 p.m.

United Center| 1901 W Madison St. | $39.95 – $295.95

Turn up this December with some of Hip-Hop’s biggest stars at WGCI’s Big Jam 2019. Major acts for this year’s Big Jam features Migos, DaBaby, G Herbo, Wale, Megan Thee Stallion, Yella Beezy, Jacquees, and Tink. To purchase tickets to the concert, visit the website here.

Sam Trump’s Nat Cole Tribute w/ Wind Orchestra

Sundays | December 1st & 15th | Time Varies

Location Varies | Free

Experience the music of one of Chicago’s most infamous musicians, Nat King Cole this December 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.

Bundle up and explore the city of Chicago this winter. For ideas on things to do, check out these winter hangouts—these are fun ways to explore Chicago any day of the week.


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