Skip to contents
Citywide

16 Things To Do In Chicago This Weekend: A Christmas Crawl, Martini Fest And Lots Of Holiday Markets

You can also skate while wearing your ugliest sweater, enjoy a night of live jazz and support local artists at Elephant Room Gallery's latest exhibition.

Featuring more than 100 vendors, the Randolph Street Market will be open Dec. 17-18.
Provided
  • Credibility:

CHICAGO — Do some last-minute holiday shopping, go skating in an ugly sweater, take holiday photos with your dog.

Here are 16 things to do in Chicago this weekend:

Randolph Street Holiday Market

10 a.m.-5 p.m. Saturday-Sunday

Plumber’s Hall, 1341 W. Randolph St.

Shop from more than 125 vendors at this European-style antique and vintage market. This three-floor event also features live entertainment, a market bar and local eateries so you can sip and snack while you browse. Tickets starting at $10 for general admission are available online.

Ugly Sweater Skate

4:40-6:10 p.m. Saturday, 4:30-6 p.m. Sunday

McFetridge Sports Center, 3843 N. California Ave.

Grab a festive sweater and skate through the evening. Admission is $5 for skaters 13 and older, or $4 for skaters 12 and under. Skate rentals are $3.

Ravenswood Light Up Nights

5-10 p.m. Friday-Sunday

On the two blocks bordered by Ashland, Montrose, Damen and Lawrence avenues

This free festival consists of a self-guided walking tour of lit-up homes competing for the title of “Best in Glow.” Local businesses will also have food and drink promotions, special events and prizes. You can also look out for Santa riding a bicycle, keep an eye out for Mr. Grinch, listen to jazz musicians on a porch, warm up at stations offering hot cocoa and more.

Holiday Artisan Market

Noon-4 p.m. Sunday

The Joinery, 2533 W. Homer St.

There will be 20 vendors offering jewelry, home goods, art prints, bags, pet items, candles and more at this family- and dog-friendly market. There will also be food from Eatin Puerto Rican, free hot cocoa, a chance to snag a selfie with Santa, a toy giveaway, ornament decorating activities and more. Admission is free and you can reserve a spot online.

The 12×12 Show At Elephant Room Gallery

5-7 p.m. Friday, noon-5 p.m. Saturday

Elephant Room Gallery, 704. S. Wabash Ave.

This fifth annual art show is on display through the end of the year. You can check out The 12×12 artwork this weekend, or you can contact the gallery for other viewing opportunities. You can also shop the exhibition online.

Windy City Made Holiday Market

Noon-6 p.m. Sunday

Stan Mansion, 2408 N. Kedzie Blvd.

You can shop local in Logan at this inaugural holiday market. There will be more than 50 local artists, artisans and vintage vendors, plus tasty holiday cocktails. You can buy $5 tickets online.

Live Jazz Feat. Freddie Franken Group

10 p.m. Saturday

Porkchop, 1132 W. Grand Ave.

Enjoy an intimate, candle-lit night of live jazz music by the Freddie Franken Group. There is a $5 cover, and you can pay in advance online. There will also be food, including starters for half-off, and cocktails.

Renegade Craft Fair

11 a.m.-5 p.m. Saturday-Sunday

Morgan Manufacturing, 401 N. Morgan St.

Renegade is returning to Chicago this weekend with over 170 curated artists. Shop from local and national businesses for handmade goods, last-minute holiday gifts and more. Admission is free but donations up to $12 are suggested.

The Silver Room 25th Anniversary Party

Noon-8 p.m. Saturday

The Silver Room, 1506 E. 53rd St.

The Silver Room is celebrating 25 years in business with a BYOB party. There will be live music, raffles, trivia, plus snacks and beverages.

Holiday Photos With Your Dog

11 a.m.-3 p.m. Sunday

The Anti-Cruelty Society, 157 W. Grand Ave.

Get holiday photos with your dog at this event hosted by The Anti-Cruelty Society. The photo will be emailed to you after the photoshoot. Space is limited so be sure to reserve a spot online.

Ugly Sweater Day Party

Noon-5 p.m. Saturday

Tree House and Tunnel, 149 W. Kinzie St.

Enjoy a complimentary brunch buffet, drinks, Santa hats, a live DJ spinning party jams and holiday tunes, giveaways and more at Chicago’s “biggest holiday party.” Tickets for $15-20 are available online.

The Elfed Up Christmas Crawl

2-10 p.m. Saturday

Headquarters Beercade, 213 W. Institute Place

Put on your elf ears (that come with your tickets) and party at River North bars this weekend. Tickets for $15-25 are available online.

Credit: Provided
You can celebrate a Celtic Christmas this weekend at the Cherish the Ladies’ traditional Irish concert.

Cherish The Ladies Holiday Concert

4 p.m. Sunday

Mayfair Theatre. 4626 N. Knox Ave.

Cherish the Ladies is bringing its success as one of the topic Celtic groups in the world to the Mayfair Theatre this weekend, offering traditional Irish music and dance. The upcoming concert features their signature sound on classic carols such as “O Come All Ye Faithful,” “The First Noel” and “Silent Night.” You can purchase general admission tickets for $35 online. Group discount sales are also available.

Share Your Home For The Holidays

11 a.m.-2 p.m. Saturday

Burning Bush Brewery, 4014 N. Rockwell St.

Share your home with a foster animal in need this holiday season. There will be dogs in need of fostering at this recruitment event, and you’ll be able to learn more about One Tail at a Time’s foster program, go through a brief orientation process, meet some pups and talk to staff about for more information.

Bantu Fest Community Day

Noon-4 p.m. Saturday

KLEO Community Family Life Center, 119 E. Garfield Blvd.

This is a free event aimed to support and help low-income families, homeless residents, local youth and the community as a whole. There will be free hot meals, canned goods, coats and clothes, toys and books. There will also be live performances and workshops. You can help out by donating items or volunteering at the event, or you can simply attend and enjoy the day.

Martini Festival

4-7 p.m. Saturday

Hubbard Street Inn, 110 W. Hubbard St.

Sip and taste over a dozen martini varieties, take trendy, Instagram-worthy photos and more. You can buy tickets for $59 and $79 online.

Subscribe to Block Club Chicago, an independent, 501(c)(3), journalist-run newsroom. Every dime we make funds reporting from Chicago’s neighborhoods.

Click here to support Block Club with a tax-deductible donation. 

Thanks for subscribing to Block Club Chicago, an independent, 501(c)(3), journalist-run newsroom. Every dime we make funds reporting from Chicago’s neighborhoods. Click here to support Block Club with a tax-deductible donation.

Listen to “It’s All Good: A Block Club Chicago Podcast”: