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!
Hop on the Holiday Trolley
Decked out in your favorite holiday attire, you are invited to join in the festive celebration of the season at the Holiday Trolley and Pizza with Santa! Guests can board this special trolley for a delightful journey through the streets of Wood Dale. The ride promises a cheerful experience filled with Christmas Carols, glimpses of festive homes, and holiday-themed trivia. Upon returning, participants will have the opportunity to visit Santa, enjoy pizza and treats, and do some holiday crafting.
Date: December 15
Time: 5-9PM
Cost: $25+
Location: The Recreation Complex, 111 E Foster, Wood Dale
More info: wdparks.org
Brunch with Santa in Woodridge
It’s Santa Season at Seven Bridges Golf Club! Head to Woodridge for a visit with Jolly Ol’ Saint Nick and savor a delicious breakfast buffet at The Dock Bar and Grill. Enjoy a unique dining experience with a carefully crafted menu and indulge in carving stations, made-to-order omelets, pastries, and much more. Don’t miss this festive morning with Santa and exceptional culinary delights!
Date: December 17
Time: 9AM-3PM
Cost: $19.95+
Location: The Dock at Seven Bridges, 1 Mulligan Dr, Woodridge
More info: exploretock.com
Find the Magic Slipper in Oakbrook Terrace
Step into the enchanting world of Cinderella at Drury Lane Theatre, where the classic fairy tale comes to life with a magical musical twist. Be transported to a realm of dazzling costumes, breathtaking sets, and the timeless story of a kind-hearted heroine whose life takes a magical turn. Don’t miss the chance to experience the wonder and charm of a favorite princess, Cinderella, in this spectacular theatrical show.
Date: Runs through January 7
Time: Varies by day
Cost: $85+
Location: Drury Lane Theatre, 100 Drury Lane, Oakbrook Terrace
More info: drurylanetheatre.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
