Alfredo Medrano

Jammie Jingle Fun at Park No. 571

Park No. 571 is hosting a holiday party for the teensiest of South Siders: toddlers from ages one to three (and their parent plus-ones, of course). Crawl, stroller, and skip over to the park by the river for a morning of making crafts, dipping cookies in milk, and writing letters to Santa. Pajamas welcome. (Sarah Fineman)

Park No. 71, 2828 S. Eleanor St. Wednesday, December 11, 10:30am–12pm. $2 for a children’s ticket.

Walden Holiday Market

The Walden Collective will have something for all your holiday needs at their annual Holiday Market. This market features locally made gifts like handcrafted metalsmith jewelry by Dawn McHugh. Music, dessert, craft cocktails, and more! (Erica Knox)

The Walden Collective, 99th & Walden Parkway. Thursday, December 12, 6pm–9pm. Free admission.

Holiday Concert at Armour Square Park

Tired of waiting for Christmas carolers to come around? Bring thee and thy family to the holiday singers, who will be at Armour Square Park next Saturday. Head over to listen as a chorus from the VanderCook School of Music performs a suite of classic holiday melodies. (Sarah Fineman)

Armour Square Park, 3309 S. Shields Ave. Friday, December 13. 2pm–6pm. Free.

Pre-Kwanzaa Holiday MarketPlace

Celebrate the Kwanzaa season early, especially principles four (Ujamaa—Cooperative Economics) and six (Kuumba—Creativity) with Africa International House as they present two days of shopping, food, raffles, clothing giveaways, and some of the most inspiring entertainment around. Experience jazz legend Maggie Brown, spoken word artist P.O.E.T., and songs by Henry H. Weddington School for the Performing Arts, along with a special presentation by Dudley’s Hair Show, programs by the Earth Center, radio personalities AC Green and Clara Hubbard, and so much more! It’s family friendly, it’s fun, and it’s free! (Nicole Bond)

Africa International House, 6200 S. Drexel at Harris Park. Friday, December 13, 2pm–8pm; Saturday, December 14, 10am–7pm. Free admission.

Beverly’s 4th Annual Cookie Crawl

Jennifer Chavez

To encourage local celebration, the Beverly Area Planning Association will host a cookie-guided tour of the neighborhood’s small businesses. Reserve a tin ahead of time to ensure a piece of the action, and on Saturday, the shopkeepers (exact shop names to be dropped day of) along a mile of Western Ave will be ready to fill participants’ tins with a full melange of sweet treats. It’s a chance to check out local businesses for gift ideas, engage in some community cheer and, most importantly, fill your home with cookies. (Sarah Fineman)

Begins at Beverly Art Center, 2407 W. 111th St., then progresses along Western Ave. Saturday, December 14, 11am–4pm. $25 per cookie tin. tins must be pre-purchased at 

Christmas Posada in Pilsen!

Sones de México Ensemble returns this year with another Christmas Posada. Featuring music, food, and cheer, it is sure to be a good time. Enjoy a performance by the Ensemble. Hear guitar music from the graduating students. Sing Christmas carols. Break into a piñata. Bring a dish to share, and try dishes from others. Free and family friendly, just be sure to bring food or drinks! (Joshua Falk)

Holy Trinity Croatian Roman Catholic Church, 1850 S. Throop St. Saturday, December 14, 11am–1pm.

Bantu Fest Community Day

This free day of community support will feature hot meals, coat and clothing giveaways, healthcare services, toys, canned goods, bus passes, books, workshops, performances and more. All free for those in need. All donations of money, goods or services are welcome and tax deductible. If you need something, come. If you have something to give, come. (Nicole Bond)

K.L.E.O Community Center, 119 E. 55th St. Saturday, December 14, 1pm–5pm. Free. All are welcome.

Holiday Market at Lo Rez Brewery

Lo Rez’s jam-packed holiday market will feature all the giftable classics from ceramics to plants, and a hot chocolate bar in addition to plenty of the Pilsen brewery’s own concoctions on tap. Grab a meal from one of the food vendors and window-shop homemade art, or go all out and hit everyone on your gift list. Those suffering from shopping stress can relax with a beer and listen to live music. Donations to this year’s featured charity, the nonprofit Streetwise, are encouraged. Grab a hot chocolate on the way out to keep warm. (Sarah Fineman)

2101 S. Carpenter St. Saturday, December 14, and Sunday, December 15, 7pm–8:30pm. Free. (888) 404-2262.

Shedd After Hours Polar Party 

Sol Salinas

Adults twenty-one and over are invited to chill at the Shedd Aquarium with the polar bears and learn how they thrive in icy waters. While there, enjoy sugar cookie cocktails and seasonal snacks. Then stay to win prizes for Arctic Aquatic Trivia and Holiday Sweater contests. (Nicole Bond)

Shedd Aquarium, 1200 S. Lake Shore Dr. Wednesday, December 18, 6pm–10pm. Tickets available online only. $24.95; $19.95 for Chicago residents and $14.95 for Shedd members. Photo ID required for entry. (312) 939-2438.

A Charlie Brown Christmas at Open Outcry Brewery

Not yet in the holiday mood or counting the days until December 25? Love the idea of music, food, and libation in one location? Consider a visit to Open Outcry Brewery in Morgan Park for a live rendition of the Charlie Brown Christmas soundtrack (performed by The Christmas-Tree O). The event is free, and the menu will include comfort food appetizers, sandwiches, burgers, and pizza. Seating will be first come, first served, and early arrival is recommended. (Michelle Anderson)

Open Outcry Brewery, 10934 S. Western Ave. Thursday, December 19, 8:30pm–10pm. Free admission. (773) 629-6055 (taproom), (773) 366-3365 (kitchen).

House Music with Santa at West Pullman

In most places, Santa comes to your house. But in Chicago, Santa brings the house to you—house music, that is! For the third year in a row, Santa will fill West Pullman Park with house music, organized by the Chicago Parks District. The event will feature arts and crafts and a chance to get a picture with Santa. All ages, no charge. Bring kids, friends, and family, and dance the night away! (Joshua Falk)

West Pullman Park, 401 W. 123rd St. Thursday, December 19, 5pm–8pm.

Asleep with the Fishes: Winter Wonderland 

Ever see the movie Night at the Museum? How about a night at the aquarium where families and groups with children ages five to twelve can explore all the open exhibit spaces, make aquatic crafts, participate in a scavenger hunt, and more, overnight! Grab your sleeping bag, toothbrush, fuzzy slippers and go! No air mattresses please. (Nicole Bond) 

Shedd Aquarium, 1200 S. Lake Shore Dr. Starts Friday, December 20, 6pm. Ends Saturday, December 21, 8:30am. Tickets start at $85 per person and $70 for Shedd members.

Hyde Park Handmade

As Hyde Park Handmade enters its sixth year, it presents an artisans’ bazaar and farmers’ market event in collaboration with the Promontory. On December 22, you can browse locally made goods and works by creatives from Bronzeville, Woodlawn, and Hyde Parkto name a few! Items for sale include fashion, home goods, jewelry, and products from urban farms. The event includes music from local DJs, and both food and beverages are available in the Promontory restaurant (floor level). The Hyde Park Handmade Bazaar might offer the opportunity for a great two-for-one, so take along some friends, enjoy the camaraderie of the season, and find quality, unique gift items.

Hyde Park Handmade, Promontory Restaurant (second floor), 5311 S. Lake Park Ave. West. Sunday, December 22, 12pm–4pm (may close early at vendors’ discretion). Free admission.

Motown for Kids Holiday Celebration

The music of Diana Ross, Stevie Wonder, Gladys Knight, the Temptations, and more will be played at a kid-friendly volume by the Rock and Roll Play House Band. Children age ten and under, accompanied by an adult, can dance, sing, play games, hear stories, and have a holly jolly time, all while experiencing the Motown sound. Little ones under age one get free admission. By attending this event, patrons consent to their image (with or without their voice) being included in photographs and/or film and videotape of the event, and give Thalia Hall, The Rock and Roll Playhouse and their respective licensees and assigns the absolute and irrevocable right and permission to use and publish such content in any and all media, whether now known or hereafter developed. Just so you know. (Nicole Bond)

Thalia Hall, 1807 S. Allport St. Sunday, December 22; doors open,11am, show 11:30–12:30pm. $15.

Comedy Laugh Fest

Get your pre-New Year’s laugh on with a comedy smorgasbord featuring Cedric the Entertainer, D.L. Hughley, Eddie Griffin, Nephew Tommy, and Deon Cole. Yupall of them! (Nicole Bond)

Wintrust Arena, 200 E. Cermak Rd. Saturday, December 28, 8pm. $49–$129.

NYE 2020—Afrobeats, Hip Hop, Reggae, Soca

Ring in the new decade at The Sage Room (formerly the Velvet Lounge) for a stylish and intimate celebration for up to 150 guests only—so get there early! Wear something festive. And enjoy DJ-selected Afrobeats, Hip Hop, Reggae, and Soca music and a midnight champagne balloon and confetti drop. Table, bottle, and VIP service available. (Nicole Bond) 

Sage Room Chicago, 67 E. Cermak Rd. Tuesday, December 31, 9pm–2am. Ages 21+. Tickets $20–$250. For more information, or to reserve tables and bottle service call (773) 512-9875.

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