THIS WEEKEND IN CHICAGO – All Aboard for Holiday Fun!
Just three weekends left before celebrating Christmas! Enjoy some holiday fun this weekend from unique holiday shopping shows to holiday light displays to plenty of family-friendly fun at various holiday indoor/outdoor events!
A favorite Chicago holiday experience transforms 170,000 square feet into a festive holiday playground for families at Winter WonderFest now through January 4, 2026, at Navy Pier’s Festival Hall (600 E. Grand Ave.) in the Streeterville neighborhood. Enjoy twinkly light displays and a towering 42-foot Holiday Tree as you discover endless ways to play such as family favorites like the classic kiddie train, electric bumper cars, the new motorcycle jump, bounce houses, and slides as well as the heart-pumping rides like the Cliffhanger and Zero Gravity. When you need a break from playing, enjoy tasty treats and sips, live music and special performances at the Winter Wonder Stage, take in a round of ice skating, and much more. Plus, each ticket includes one ride on the Pier’s Centennial Ferris Wheel with enclosed gondolas. There’s no need to worry about snow drifts or windchills at this event!
Returning for its 7th season, this year’s Jack Frost Christmas Pop-Up runs now through January 6, 2026, at Fulton Market (170 N. Green St.) in the West Loop neighborhood. This outdoor experience on two acres will make your season sparkle with a light-filled Christmas tree walk; a Christmas market featuring pop-up holiday shops; an opportunity to snack on holiday treats and sip on boozy hot cocoa and other holiday cocktails; plenty of holiday photo ops; and a variety of activities like bumper cars, ice skating, axe throwing, curling, and more. It’s a holiday party for all ages and a great way to make some winter memories at this larger than life, multi-sensory adventure in the heart of Chicago!
Still working on your Christmas gift list? This may be your lucky weekend, as the One of a Kind Holiday Show returns to the 7th Floor of the Merchandise Mart (222 Merchandise Plaza) in the River North neighborhood this Saturday (10 a.m.-7 p.m.) and Sunday (10 a.m.-5 p.m.). This seasonal bazaar brings together over 600 exceptional artists, designers, and makers spanning a variety of media including accessories, bath and body, children’s products, holiday and home goods, fashion, jewelry, ceramics, fine art, and more. In addition, the show includes live music from local musicians, live artist demonstrations, artisan culinary creations, a gourmet market, and for guests 21+, Bailey’s is offering complimentary samples of delicious holiday treats. And, besides being a truly unique experience, and Chicago’s premier holiday shopping destination for unique, handmade gifts for everyone on your holiday gift list, a portion of ticket proceeds will benefit Ann & Robert H. Lurie Children’s Hospital in Chicago!
Another of Chicago’s most popular and beloved Christmas traditions is celebrating its 42nd anniversary this year with The Music Box Christmas Double Feature and Sing-A-Long now through December 24th at the Music Box Theatre (3733 N. Southport Ave.) in the Wrigleyville neighborhood. Each screening features a 25-minute preshow beginning at the listed showtime with a short cartoon and Christmas caroling with Santa. Then sit back in your plush theater seat with popcorn, snacks, and drink in hand to enjoy the showings of White Christmas and It’s a Wonderful Life. It’s a great way to make this old-fashioned event a part of your family’s holiday tradition!
Did you know that the Chicagoland area has some great holiday light events that you can enjoy from the comfort of your own car? Well, one such display runs now through January 4, 2026, from 5:00 p.m. to 9:00 p.m. at Light of Christmas Drive Thru at Rate Field (3326 S. Wentworth Ave.) in the Bridgeport neighborhood. Visitors drive through a gleaming tunnel of over one million LED lights that are synchronized to holiday music. In addition, there are several ticket options which include the Drive Thru, the Drone Experience, the Hay Barrel Ride, the Light Show and Movie, the Walk the Show, and the Trolly Tour which combines the Drive Thru along with enchanting stops at the iconic Christkindlmarket and Navy Pier’s Light Up the Lake. It’s a great way to enjoy the holidays while staying warm!
Sue Moss and Dean’s Team Chicago
