Things To Do This Weekend In And Around Chicago: Dec. 20-22

Shannon Blum
December 20, 2019 - 7:58 am

CHICAGO (WBBM NEWSRADIO) -- It's beginning to look a lot like Christmas! It is the weekend before Christmas, and Hanukkah, and winter activities in Chicago are in full swing! From Christmas markets and light displays, to holiday exhibits, ice skating, concerts, and more there is plenty to keep you busy and in the holiday spirit this weekend!

And as for sports, the Chicago Bears play at home this weekend, so if you are looking to escape the holiday madness and want to cheer on the Bears, despite them being out of the plays, then head to Soldier Field.

Here's a look at things to do this weekend in and around Chicago.

Jack Frost Winter Village & Christmas Tree Farm
Jack Frost Winter Village & Christmas Tree Farm

Jack Frost Winter Village & Christmas Tree Farm

There’s no need to head inside when the weather turns cold. The dropping temperatures, first snowfalls, and icy ambience awakens your need to go outside and play. And that's why winter is the best time to throw a massive, outdoor festival in downtown Chicago! The creative mastermind team behind Jack’s Pumpkin Pop-Up and Frosty’s Christmas Pop-Up Bar, are back for the first time ever, larger-than-life, multi-sensory spectacle of Holiday lights, unique winter Instagram photo opportunities, an Christmas Tree Farm and S-now much more! More info. 

Where: 1455 N. Elston Ave.

When: Now through March; Monday-Friday 4-10 p.m.; Saturday & Sunday, 11 a.m.-10 p.m.

Cost: Varies

A Very Harry Christmas Pop-Up
Jeremy Steffen/Facebook

A Very Harry Christmas Pop-Up Bar

Would you rather stay at Hogwarts this Christmas? Well now’s your chance. Calling all witches and wizards, and muggles too, Replay Lincoln Park is bringing a Harry Potter pop-up all month long. Replay Lincoln Park’s Great Hall will be decked from floor to roof with magical decorations and holiday cheer. Replay has partnered with Zizi's Cafe to serve up a variety of Harry Potter-inspired snacks including Hogwarts Housecup Chicken, Huffle Pizza Puffs, and Paddington Burge. There will also be a variety of custom cocktails. More info. 

Where: 1455 N. Elston Ave.

When: Now through March; Monday-Friday 4-10 p.m.; Saturday & Sunday, 11 a.m.-10 p.m.

Cost: Varies

Brett Eldredge
Rick Diamond/Getty Images for Target

Brett Eldredge: GLOW Live

Brett Eldredge returns to the Chicago Theatre with GLOW Live, a night of holiday hits. Listen (and sing along) to your favorite holiday hits like Baby, It’s Cold Outside and It’s Beginning to Look A Lot Like Christmas. More info.

Where: Chicago Theatre, 175 N. State St.

When: Friday, 8 p.m.; Saturday, 8 p.m.

Cost: Varies

Steve Byrne
Jason Davis/Getty Images for Bud Light

Steve Byrne

In need of a good laugh? Check out Steve Byrne this weekend at Chicago Improv! Steve Byrne has risen through the ranks of the comedy world to become one of the industry’s most innovative and sought-after performers. More info. 

Where: Chicago Improv, 5 Woodfield Rd., Schaumburg

When: Friday, 7:30 p.m. & 9:45 p.m.; Saturday, 7 p.m. & 9:15 p.m.

Cost: $22

Navy Pier Winter WonderFest
Nick Ulivieri Photography

Winter WonderFest

Bring the winter fun inside at Navy Pier’s Winter Wonderfest, as they fill their gigantic 170,000-square-foot Festival Hall with an ice skating rink, carnival rides, a tubing hill, seasonal activities and piles of holiday decorations. Bring the kids and avoid the cold for an afternoon. More info.

Where: Festival Hall, Navy Pier, 600 E. Grand Ave.

When: Now through Jan. 12

Cost: Varies

Christmas Tree Chicago 2019
WBBM Newsradio/Jim Gudas

City of Chicago Christmas Tree

Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star—and it's not too far of a walk from Christkindlmarket in Daley Plaza. Spectators can check out the festive tree near Washington Street and Michigan Avenue through Monday, January 6, 2020. More info. 

Where: Millennium Park, 55 N. Michigan Ave. 

When: Now through Monday, Jan. 6.

Cost: Free

Snow falls on the Cloud Gate sculpture in Millennium Park on February 1, 2011 in Chicago
Scott Olson/Getty Images

Caroling at Cloud Gate

All are invited to bundle up and belt out holiday classics during Caroling at Cloud Gate located on the Millennium Park’s iconic Cloud Gate Plaza. The festive series is part concert, part sing-along with some of our city's most entertaining choirs on Fridays from Nov. 29 through Dec. 20 beginning at 6 p.m. The caroling is led by the likes of the Sounds Good! Choir (Nov. 29), Mark Hubbard and The Voices (Dec. 6), the Chicago Children’s Choir (Dec. 13) and the Wicker Park Choral Singers (Dec. 20). Songbooks will be distributed at this event. More info.

Where: Millennium Park, 55 N. Michigan Ave.

When: Fridays, Nov. 29, Dec. 6, Dec. 13, and Dec. 20; 6-7 p.m.

Cost: Free

Millennium Park Ice Rink
Ice-skating at the Millennium Park ice rink (Mike Ramsey/WBBM Newsradio)

Ice Skating in Millennium Park

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Admission to the rink is free, and you can rent skates for $13–$15. The most popular time to hit the rink is in the evening, so show up earlier if you don't feel like waiting in line for your chance to slide around. Take advantage of free skating lessons on Fridays at 11 a.m. and Saturdays and Sundays at 9 a.m. If it seems too warm to skate, call ahead—this rink is open through March 8, weather permitting. More info.

Where: Millennium Park, 55 N. Michigan Ave. 

When: Friday, Nov. 15-March 8 (weather permitting)

Cost: Free, skate rentals $13–$15

WBBM Newsradio/Nancy Harty

Ice Skating at Maggie Daley Park

Situated in the heart of downtown Chicago, with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. The skating ribbon is dramatically different from typical civic ice rinks, creating a multi-sensory activity that is integrated into the landscape. Skaters can experience “alpine in the city” as they lace up their ice skates and follow a path twice the length of a lap around a traditional skating rink. More info. 

Where: Maggie Daley Park, 337 E. Randolph St. 

When: Friday, Nov. 15-March (weather permitting)

Cost: Free, skate rentals $13–$15

Christkindlmarket 2019 Boot Mugs
Christkindlmarket Chicago/Facebook


You haven't experienced the holidays in Chicago until you've stepped into this giant open-air market inspired by a similar seasonal tradition in Nuremberg, Germany. At Christkindlmarket, guests can shop handcrafted items like nutcrackers, cuckoo clocks, beer steins and glass ornaments and nibble on potato pancakes, hot pretzels, schnitzel, döner and chocolate-covered treats. And no trip to Christkindlmarket is complete without a steaming mug of Glühwein, a traditional hot spiced wine (there's also hot cocoa for the kids) – and don’t forget to order it in the keepsake boot mug! More info. 

Where: Daley Plaza, 50 W. Washington St.

When: Friday, Nov. 15-Dec. 24; Sunday-Thursday,11 a.m.-8 p.m.; Friday & Saturday, 11 a.m.-9 p.m.

Cost: Free

Christmas Around the World
WBBM Newsradio

Christmas Around The World

Every year, the Museum of Science and Industry puts up its 45-foot-tall Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors can admire the 30,000 lights that cover the trees and stick around for the "snow" that falls from the rotunda every 30 minutes. During the weekend, live performances of holiday music fill the room, lending some additional seasonal cheer to your day at the museum. More info. 

Where: Museum of Science and Industry, 5700 S. Lakeshore Dr.

When: Thursday, Nov. 14-Sunday, Jan. 5

Cost: Included in museum admission

Winterland at Gallagher Way
Gallagher Way Chicago/Facebook

Winterland at Gallagher Way

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's off-season. The public square's Winterland event series offers an array of seasonal, family-friendly activities, including an 8,000-square-foot ice rink, curling and skating lessons, holiday movie screenings and visits from Santa Claus. Beloved holiday bazaar Christkindlmarket also hosts an outpost at Gallagher Way, bringing shopping and glühwein north of the Loop. Plus, look out for wreath-making workshops, breakfasts with Santa and a tree lot at Big Star. More info. 

Where: Gallagher Way, 3637 N. Clark St.  

When: Friday, Nov. 15-March (weather permitting)

Cost: Free, event/activity pricing varies

Frosty’s Christmas Bar
Frosty’s Christmas Bar

Frosty’s Christmas Bar

Now through Jan. 5, Frosty’s Christmas Bar is popping back up for its third year, and it’s determined to turn any Scrooge into a festive holiday elf. Experience elaborate holiday decorations that will inspire your holiday décor, to the extreme. Featuring life size toy soldiers, Santa, and elves along with non-stop holiday music spinning until 4 a.m., this is the ultimate seasonal experience you won’t want to miss! With four bars, three levels and two dance floors, Frosty’s Christmas Bar takes your holiday celebration to the next level. More info.

Where: Frosty’s Christmas Bar, 809 W. Evergreen Ave.  

When: now-Jan. 5

Cost: Varies

Lincoln Park ZooLights
Lincoln Park Zoo / Julia Fuller

ZooLights at Lincoln Park Zoo

The most wonderful time of the year deserves the most wonderful event of the year. For that, Lincoln Park Zoo invites you to join them in celebrating 25 years of ZooLights at Lincoln Park Zoo. This one-of-a-kind, festive holiday experience offers a free, merry, family-oriented celebration of joy right in the heart of the city. ZooLights features hundreds of luminous displays and incredible seasonal activities, all under the glow of 2.5 million lights. Ice sculpture carving, strolling carolers and Santa are regular fixtures of the event, but you'll also find ticketed happenings like a holiday market (Dec 3), an adults-only night (Dec 5), a live performance of music from A Charlie Brown Christmas (Dec 15) and a Zoo Year's Eve celebration (Dec 31). More info. 

Where: Lincoln Park Zoo, 2001 N. Clark St.

When: Fridays, Nov. 29 through Sunday, Jan. 5

Cost: Free

A 41-foot-tall Talking Tree near the north entrance greets guests to Brookfield Zoo’s Holiday Magic.
Chicago Zoological Society

Holiday Magic at Brookfield Zoo

More than one million lights cover the trees, fences and structures in the Brookfield Zoo at this annual holiday event. Attendees are encouraged to sing carols to the animals, explore the zoo's indoor exhibits and view light shows. This year, Holiday Magic will feature a Chicago Wolves skating rink, where visitors can slide around while admiring the decorations. More info. 

Where: Brookfield Zoo, 8400 31st St., Brookfield

When: Saturday, Nov. 30 through Tuesday, Dec. 31

Cost: $22, children (3-11) $16

Lightscape at The Chicago Botanic Garden
Photo courtesy of The Chicago Botanic Garden


The Chicago Botanic Garden hosts a new display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along a one-mile path, the night comes alive with color, imagination, and sound, from a playful choir of singing trees to a spectacular waterfall of light. At times, you’ll find yourself in the center of it all — stepping inside a cathedral of golden light, walking down an avenue of luminous linden trees, moving through colorful ribbons of light. More info. 

Where: Chicago Botanic Garden, 1000 Lake Cook Rd., Glencoe 

When: Friday, Nov. 29 through Sunday, Jan. 5

Cost: Varies

Morton Arboretum

Illumination: Tree Lights at Morton Arboretum

When the weather gets cold, the trees at Morton Arboretum light up in a sea of color at this popular winter event. Guests at Illumination walk down a one-mile path through the forest, admiring the magical display and seasonal music. Enjoy the display while strolling along a one-mile path and then warm up by a crackling fire with hot beverages and s’mores. More info. 

Where: Morton Arboretum, 4100 Illinois Rte 53, Lisle 

When: Saturday, Nov. 23-Jan. 5, first entry at 4:30 p.m., last entry at 8:30

Cost: Varies

Skating in the Park
Village of Rosemont

Skating in the Park

Enjoy free ice skating during the holiday season as well as "Characters on Ice" every Sunday in December in Rosemont. More info. 

Where: Parkway Bank Park, 5501 Park Pl., Rosemont  

When: Friday, 4-10 p.m.; Saturday, 11 a.m.-10 p.m.; Sunday, 9 a.m.-9 p.m.

Cost: Free, skate rentals $8

Aurora’s Festival of Lights
Maritza Partida

Aurora’s Festival of Lights

It’s almost Christmas! One of the largest free, outdoor, drive-through holiday light displays in Northern Illinois, the Aurora Festival of Lights, returns for its 13th year in 2019 with even more dazzling displays that will delight both adults and children. More info. 

Where: Phillips Park, 1000 Ray Moses Dr., Aurora  

When: Now through Dec. 26, 5-9 p.m.

Cost: Free

Chicago Bears v. Kansas City Chiefs

The Bears may be out of the playoffs, but there are still a few more weeks left of football. Cheer on the Chicago Bears on Sunday when they on the Kansas City Chiefs at home! More info.

Where: Soldier Field,

When: Sunday, 7:20 p.m.

Cost: Varies