Embrace the chilly winter days with activities that will make your season sparkle. From exploring winter markets to indulging in delicious food & drinks while warming up inside, there is so much to experience and enjoy. Embark on snowy trails and visit local landmarks to add a touch of adventure to your winter plans. Don’t miss out on the exciting events scheduled for this weekend to fully appreciate the beauty of the season!
All Aboard the Winter Express
Hop on board for a magical journey to Winnetka Golf Club with the Winnetka Winter Express! Bring the whole family to see the enchanting Polar Express come to life right from the comfort of your car. While watching the film, every child will be treated to hot chocolate, a cookie, popcorn, and the chance to pen a letter to Santa. It’s a festive evening under the stars, combining the joy of holiday cinema with delightful treats for an unforgettable family experience.
Date: December 16
Time: 5PM
Cost: $50
Location: Winnetka Golf Club, 1300 Oak St, Winnetka
More info: winpark.org
Show Off Your Ugly Sweaters in Skokie
Embark on a journey of style and merriment at this year’s Ugly Sweater Skate! You are invited to unleash the beauty in your most eye-catching, jaw-dropping holiday sweaters, transforming the ice rink into a festive fashion runway. This event promises a playful celebration where the spirit of the season meets the whimsy of holiday fashion. Don’t miss out on this delightful gathering that turns ugly sweaters into a showcase of holiday cheer!
Date: December 17
Time: 2PM
Cost: $7+
Location: Skatium Ice Arena, 9340 Weber Park Place, Skokie
More info: skokieparks.org
Meet Santa at District Yards Brewery
Get ready to jingle and mingle at the District Brew Yards Santa Visit, where the magic of the season meets the craft of brewing! Santa himself will be spreading cheer and posing for photos. Savor the joyous atmosphere as you enjoy a selection of seasonal brews. Bring the whole family or gather your friends for a memorable evening of laughter, good company, and the chance to share your holiday wishes with Santa.
Date: December 16 + 17
Time: 12-2PM
Cost: Free
Location: District Yards Brewery, 700 N Milwaukee Ave, Wheeling
More info: visitchicagonorthshore.com
Singing in a Winter Wonderland
Join the League of Chicago Theatres for a night of singing with the sparkling lights of the Chicago skyline surrounding you! This holiday program will bring some Christmas joy to downtown with sing-along favorites. Bring the family and warm up those voices for a night of carols!
Date: December 15
Time: 6PM
Cost: Free
Location: Milennium Park, 201 E Randolph
More info:chicago.gov
Take Note at this Holiday Shop
Field Notes is hosting a holiday shop featuring its high-quality memo books and paper goods. The event will showcase the complete Field Notes product line, including rarities from archives and other miscellaneous goods. Local artists will also be present, offering posters, prints, buttons, houseware, accessories, and gifts. Enjoy free admission, all-ages access, complimentary coffee, and baked treats!
Date: December 16 + 17
Time: 10AM-5PM
Cost: Free
Location: Field Notes HQ, 401 N Racine Ave
More info: choosechicago.com
Don’t Be a Scrooge at the Theater
The Chicago Holiday classic is back for another year of ghosts & Tiny Tim! Goodman Theatre’s A Christmas Carol is a tradition for a reason. This incredible show focuses on Scrooge as he reflects on Christmases past, present, and future. Enjoy the spectacle and heart of this long-running production that many make a regular part of their holiday season.
Date: Runs through December 31
Time: Varies by day
Cost: $25+
Location: Goodman Theatre, 170 N Dearborn
More info: goodmantheatre.org/carol
Have A Seasonal Soiree at Frosty’s Christmas Bar
Frosty’s Christmas Bar returns to Chicago for its seventh year, spreading holiday cheer through the season! Featuring elaborate decorations, including life-size toy soldiers and festive music, the bar boasts four bars, three levels, and two dance floors. Join Santa and his helpers for seasonal cocktails and dance to a mix of Christmas Classics and today’s hits. This one-stop destination is perfect for celebrating the holidays with friends, family, and co-workers until the New Year.
Date: Runs through December 31
Time: By Reservation
Cost: $23+
Location: Frosty’s Christmas Bar, 809 W Evergreen Ave, Chicago, IL 60642
More info: bucketlisters.com
Double the Feature, Double the Fun!
Celebrate the holidays with nostalgia and style with The 40th Annual Music Box Christmas Sing-A-Long & Double Feature of “It’s A Wonderful Life” and “White Christmas.” Originating from a humble snowy Christmas Eve in 1983, the Music Box Christmas Show has evolved into a beloved local tradition. Embraced by families throughout Chicagoland, this old-fashioned event features Santa Claus leading the audience in singing timeless Christmas carols with projected lyrics on the theater’s screen to ensure everyone can join in the festive chorus!
Date: Runs through December 24
Time: Showtimes vary by day
Cost: $14+
Location: Music Box Theatre, 3733 N Southport Ave
More info: musicboxtheatre.com
