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Events Happening Around Chicago During the 2020 Holiday Season

The holiday event season is looking much different this year in Chicago, however, there are still many fun things happening.

Here’s a list of virtual and in-person activities happening around the city!


Christkindle Market

Inspired by the Christkindle Market in Nuremberg, Germany, the Christkindle Market is virtual this year.   Now through December 31st you can shop online from 47 of your favorites Christkindlemarket vendors. Specialty artisan gifts as well as sweets and treats (including Glühwein) will be available for purchase — and delivered right to your front door. 

Virtual events associated with the market include German cooking demonstrations, trivia night, daily Advent Calendar prize giveaways starting December 1st.  While most activities are free, some have limited ticketed attendance. Sign up to secure your spot here!

One-of-a-Kind Show

This year’s One of a Kind Holiday Show virtual show runs from November 12 through December 6th.  Shoppers will have the opportunity to connect with over 300 participating artists’ market pages to learn about them, their creative process, and their work while shopping art, fashion, jewelry, wood, photography, glass, furniture, home goods, pet products, bath & body, and so much more!  They will be hosting many specials and even online programming. Check out the activities on the One-of-a-Kind Show’s website!

Untitled Supper Club: Dinner and a Show

Chicago’s venerable speakeasy, Untitled Supper Club, has launched a virtual dinner and a show.

This is the first time Untitled is offering its seven-time Michelin Bib Gourmand award-winning cuisine for takeout since opening in 2011 so don’t miss out. Each order comes with accessibility to a variety of entertainment from music to captivating cabaret-style and burlesque performances. The shows are accessible through a QR code placed in each order.  

Available for delivery or pick-up from 4 p.m. to 10 p.m. Wednesday through Sunday. 

Theatres Offering Virtual Shows

  • Goodman Theatre’s A Christmas Carol, from December 1-31, 2020
  •  Writers Theatre is offering two unique virtual versions of A Christmas Carol: Manual Cinema’s Christmas Carol, December 3-20, 2020. Artistic Director Michael Halberstam’s tour-de-force solo performance of A Christmas Carol will stream December 8, 2020-January 3, 2021. 
  • The College of DuPage’s McAninch Arts Center will film its production A Christmas Carol for audiences on Zoom, November 27-29, 2020.
  • Online concert offerings this season include:
    • New Philharmonic live streaming Holiday Sing-Along with the Symphony at the McAninch Arts Center December 12-13, 2020
    • Harris Theater streaming CMS at Home: Brandenburg Concertos on December 17 and 21, 2020; and Jim Brickman’s interactive concert experience Comfort & Joy at Home, presented with North Central College Fine & Performing Arts live on Zoom, December 4, 2020.
    • On December 5, 2020, Water People Theater will host an online performance of Water People Express: A Bilingual Christmas Musical Workshop for Kids.
  • Ballet Chicago will stream an archival production of The Nutcracker, on Zoom December 18-20. The Joffrey Ballet will feature the Emmy-winning PBS documentary Making a New American Nutcracker on its website from December 1-31, 2020.
  • American Blues Theater is producing its interactive, music-infused, 1940s radio broadcast tradition It’s a Wonderful Life: Live in Chicago!, performed live from actors’ homes to yours on Zoom from November 12, 2020-January 2, 2021.
  • Lookingglass Theatre brings The Steadfast Tin Soldier based on the story by Hans Christian Andersen, adapted and directed by Mary Zimmerman and filmed by HMS Media, December 1-27, 2020.
  • Steppenwolf’s production of Isaac Gomez’s new play Wally World streams online via the Steppenwolf NOW platform this December 2020.
  • PlayMakers Laboratory Theatre’s That’s Weird, Grandma: House Par-Tay features a creative line-up of holiday stories written by elementary school students, adapted and performed online by professional actors, December 7-28, 2020 online via Patreon.
  • Porchlight Music Theatre will virtually debut a “get together” on December 11, 2020 available through January 3, 2021 to celebrate the winter season. Happy Holidays from Porchlight! features Porchlight favorites performing holiday classics and winter-themed songs from a variety of music theatre productions.
  • With story, music and magic, Strawdog Theatre brings to life the family-friendly stage adaptation of Eric Kimmel’s book Hershel and The Hanukkah Goblins, online December 5-20, 2020.
  • Chicago Shakespeare Theater returns to Neverland with its wildly popular 75-minute, 2018 musical production of Peter Pan, directed and choreographed by Amber Mak and filmed by HMS Media.

Outdoor Chicago Activities

Maggie Daley Skating Ribbon

Take in the skyline as you skate the ribbon at Maggie Daley Park.  This family-friendly activity is always a highlight of winter in Chicago.

Art on The Mart

This free 30 minute program of projections happens nightly at 7:00 and 7:30 p.m. through December 31st.  Hang out on the Chicago River Walk as the Merchandise Mart turns into the largest digital art projector in the world.  Thirty-four projectors will showcase the works of renowned contemporary artists during the 2-hour shows.  The Mart spans two city blocks and is over 25 stories high, don’t miss this spectacular display! Face masks are required if watching from the Riverwalk.

ZooLights at Lincoln Park Zoo

The one-of-a-kind experience offers fun, free, family-oriented festivities, and hundreds of dynamic displays all under the glow of 2.5 million lights. The display runs from November 21st through January 3rd. Zoolights entry is $5.

Lincoln Park Zoo Lights
Photo courtesy of Lincoln Park Zoo

Illumination:  Tree Lights at Morton Aboretorum

Illumination is currently sold out, however, additional tickets are potentially added on Mondays depending on the weekly capacity evaluation.

This year’s NEW driving experience will be 30-40 minutes long. Guests will be dazzled with an unparalleled spectacle of color, light, and music. Many old favorites will return along with five newly designed sights displayed along a two-mile road highlighting the winter beauty of the Arboretum’s magnificent trees.

Tree Lights runs from November 20th through January 3rd with new later hours. The exhibition will stay open until 10 p.m. Sunday through Thursday and 11 p.m. Friday and Saturday. Tickets must be purchased in advance.

ChiTown Movies Drive-In

Enjoy blockbusters and classics under the stars this season at ChiTown Theatre Drive-In. Movies will be shown through December 24th. It’s a fun and safe experience for the whole family to enjoy.

All screenings take place at Chi-Town Movies Drive-In located at 2343 S Throop St, Chicago, IL 60608. Drive-In Admittance begins 30 minutes prior to the film’s listed start time.

Pricing is $49 per vehicle. Outside food and drink are NOT permitted at the drive-in. ChiTown Grille will deliver delicious popcorn, tacos, wings, frozen mangos, and more right to your vehicle as you enjoy the movie.  

Themed Pop-Up Bars

There are a few festive winter-themed pop-up bars happening around the city. Here’s a list:

Rudolph’s Christmas Bar

Rudolph’s Christmas Bar featuring over the top holiday decorations and all new socially interactive experiences will begin taking reservations November 23rd for groups of up to 6 people. Tables are limited to 1 hour and 45 minutes max. Restrictions are in place and masks are required. The North Pole of Rudolph’s is outside so dress accordingly.

Casey Moran’s: 3660 N. Clark Nov. 22 – Jan. 6 Mondays – Friday: 3 p.m. – 9 p.m. Saturday & Sunday: 11 a.m. – 9 p.m.

A portion of all proceeds will benefit Humble Design and Toys for Tots. On-site toy donations bins will be available for daily collection.

Santa Baby Christmas Bar

Santa Baby Bar, a multi-room, multi-level, over the top interactive Holiday experience opens November. The popular themed bar is located at Deuce’s Major League Bar: 3505 N. Clark St. Reservations are required and limited to one hour and 45 minutes max. Monday – Friday: 2 p.m. – 11 p.m. Saturdays & Sunday: 10 a.m. – 11 p.m. 21+ after 9 p.m.

The bar will be partnering with Toys for Tots and will have on-site bins for donations with daily collection.

Click here for additional Chicago experiences!

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