The Most Festive Events in Chicago This Holiday Season

Brighten up your winter.

With traditional drunken holiday parties from Santacon to TBOX cancelled for 2020, it’s time to discover a slightly more low-key way to celebrate the holidays. And if that involves drive-in holiday movies, virtual concerts, and over-the-top light displays, we’ll take it. So be grateful for what you have, wear a festive holiday mask, and celebrate the end of 2020 at these top holiday events around Chicago.

Cater your small holiday gathering with Frontier’s Holiday Meats & Catering Menu

Now through December 24
Frontier’s special meat-centric holiday menu featuring smoked prime rib, tenderloin, whole smoked turkey, and more is available the entire month of December—including Christmas Eve—so there’s no excuse for a frozen pizza Christmas.
Cost: Pricing varies

Wave to the CTA Holiday Train

Now through December 21
Various locations
Public transit doesn’t have to be a drag, as the CTA is once again dressing up its trains and buses in full holiday cheer for 2020. The CTA Holiday Train includes a six-car display decked out with festive holiday scenes, thousands of lights, and bright LED signage displays. You can’t board the train or bus this year, but you can at least wave and take photos as it goes by.
Cost: Varies

Book a virtual hang session with Kris Kringle at Santa the Experience

Now through December 24
This 10-12 minute virtual experience will guide you and your crew through five holiday scenes guided by “Elf Pickles” before culminating in a personal 5-minute video chat with Santa Claus himself. Don’t blow it.
Cost: $35-$55

Get your fill of holiday classics at a local drive-in movie theatre

Now through December 26
Various locations
One positive byproduct of this endless pandemic is the preponderance of drive-in movie locations across the city, several of which are open for the holidays for your drive-in holiday movie pleasure. Hit up Chi-Town Movies, the Drive-In at Lincoln Yards, and SeatGeek Stadium for a range of seasonal classics from Elf to Die Hard. There are also two new pop-up holiday drive-in movie experiences from the folks at Replay including the Miracle on West Madison downtown and the Holly Jolly Drive-In in Lincoln Park.
Cost: Varies

Hit a massive drive-through light display at the Aurora Festival of Lights

Now through December 27
Phillips Park, Aurora
One of the largest free outdoor holiday drive-through holiday light displays in northern Illinois returns to Aurora, with more than one mile of lights and holiday displays providing fun for the whole family.
Cost: Free (donations accepted)

Get a jump on your holiday shopping at the Christkindlmarket Virtual Christmas Market

Now through December 31
One of Chicago’s most iconic holiday events goes virtual this year with 47 Christkindlmarket vendors hawking their beloved holiday-centric wares online as part of its first-ever “Home for the Holidays” virtual market.
Cost: Depends on what you buy

See The Nutcracker screened on the side of a giant building at Art on theMART

Now through December 31
Merchandise Mart
The Joffrey Ballet’s presentation of The Nutcracker will be screened on the 2.5-acre river façade of the Merchandise Mart set to music nightly at 7 pm as part of this year’s Art on theMART digital projection series, best viewed from the Chicago Riverwalk between Wells and Franklin.
Cost: Free

Stream an audio version of A Christmas Carol from the Goodman Theatre

Now through December 31
The Goodman Theatre presents this free audio streaming version of the Charles Dickens classic for housebound revelers in 2020.
Cost: Free (donations accepted)

Get lost in a sea of lights and trees at Illumination at Morton Arboretum

Now through January 3
Morton Arboretum
One of the most beautiful locations in the Chicago metro area becomes even more enticing over the holidays as this year’s Illumination: Tree Lights at Morton Arboretum is reimagined for 2020 as a 30-40 minute driving experience.
Cost: $29-$64

Enjoy a classic Chicago holiday tradition at ZooLights

Now through January 3
Lincoln Park Zoo
It wouldn’t be the holidays in Chicago without the annual ZooLights illuminated display at Lincoln Park Zoo, a massive spectacle featuring a light maze, hundreds of large-scale displays, a holiday pop-up, and socially distanced photos with Santa.
Cost: $5

Light up the night at Chicago Botanic Garden’s Lightscape

Now through January 3
Chicago Botanic Garden
Is there any better date night than a romantic stroll on this illuminated trail through the Chicago Botanic Garden after dark? Rhetorical question.
Cost: $24-$28

Wander an urban tree farm at the Jack Frost Winter Walk & Christmas Tree Farm

Now through January 10
1467 N. Elston
Set in the same 2+-acre Goose Island location as the Jack’s Pumpkin Halloween pop-up, the Jack Frost Winter Walk & Christmas Tree Farm includes trees for purchase in an evergreen forest popping up in the middle of the city. There will be no food/drink on site, and visits are limited to 1.5 hours.
Cost: $21 - $120 

Grab some booze and seasonal snacks at The Dawson Winter Market

Every Saturday
The Dawson
Stop by The Dawson every Saturday from 11 am - 3 pm this winter for to-go cocktails, wine packs, seasonal pastries, steaks, chops, bacon, sausages, and Christmas trees and wreaths. In other words, everything you need to start the party at home.
Cost: No cover

Go on a local “treat stroll” at the Lakeview East Holiday Extravaganza

Saturday, December 5
Various locations
Support local business and sample holiday treats at the Lakeview East Chamber of Commerce’s annual Holiday Treat Stroll, with purchase necessary to prevent crowding. There is also an online component, with one-day 25% off discounts available from more than 185 local businesses.
Cost: Free

Take your shopping below deck at the Underground Art Market 2020

Starts Sunday, December 6
This DIY market that started in 2010 goes virtual for 2020 with an array of indie vendors hawking wares that focus on unique creations in the themes of recycled art, wellness, green initiatives, functional art, and more.
Cost: Free

Stream The Lawrence Arms’ annual War on X-Mas Holiday Special

Friday, December 11
Legendary Chicago punk rockers The Lawrence Arms host their annual War on X-Mas show in virtual format for 2020, with special guest appearances and plenty of “holiday weirdness” to benefit the Greater Chicago Food Depository.
Cost: $11

Move around and do some good at the Virtual Jingle Bell Run

Friday, December 11 - Sunday, December 13
With large-scale events like Chicago’s annual Jingle Jog cancelled for 2020, this virtual run still allows you to run your own route (or treadmill) as you raise money for the Arthritis Foundation. And yes, you still get a T-shirt.
Cost: $30-$35

Cruise through Christmas at the Let It Shine Lightshow

Now through January 9
1515 Lake Cook Road, Northbrook
The North Shore’s largest drive-through holiday light display features synchronized lights, glowing snowmen, sparkling candy canes, and a Santa’s bag of holiday cheer from a safe distance.
Cost: $30-$55

Hit up a Very Virtual Hanukkah

Sunday, December 13
Chicago singer/songwriter Alisa Rosenthal hosts this virtual musical livestreamed Hanukkah gathering with Hanukkah songs, stories, an ugly sweater contest and more.
Cost: $10-$15

Rock out to Glass Animals and Cold War Kids at 101.1 WKQX’s Virtual Stole

Wednesday, December 23
101.1 WKQX’s annual Night We Stole Christmas concert series goes virtual for 2020 with livestreamed performances from Glass Animals, Cold War Kids, and Wallows, all happening on December 23 (aka Festivus.)
Cost: $17.50

Say good riddance to 2020 at the New Year’s Eve Virtual 5K

Saturday, December 26 - Sunday, January 3
Chicago Sport & Social’s annual New Year’s Eve 5K takes to the interwebs for 2020 with a weeklong virtual 5K to benefit Direct Relief.
Cost: $40

Party in your car at House Party at the Drive-In New Year’s Eve Bash

Thursday, December 31
SeatGeek Stadium
What better way to close out this weird year than a New Year’s Eve party from the comfort of your car? Stop by SeatGeek Stadium for a full lineup of live house music performances with food/drink and a fireworks show. Masks and social distancing required, obviously.
Cost: $50-$225

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile