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Sing-Alongs, Polar Express Trains, and More Things To Do in Chicago This Weekend With Kids

The Millennium Park Sing-Along is a FREE holiday classic. Photo courtesy of the Department of Cultural Affairs.
The Millennium Park Sing-Along is a FREE holiday classic. Photo courtesy of the Department of Cultural Affairs.
12/3/25 - By Maureen Wilkey

Looking for the best things to do in Chicago this weekend? Here are some family-friendly events and activities to add to your list!

It's time to deck the halls! Thanksgiving has passed and the holiday season is here in Chicago. If you like singing Christmas carols, this is the weekend for you. There are carol-singing events in Millennium Park and at the JW Marriott, and it's opening weekend for Music Box Theater's sing-along double feature. Did you sleep on getting Polar Express tickets for your holiday train-loving kid? It's not too late with TWO train events that aren't sold out this weekend. Visit South Elgin or New Lenox to get a ticket to ride to the North Pole.

It's a new month, so we have a new list of best things to do in December in Chicago with kids! We also updated our list of best holiday light shows in the Chicago area, so be sure to check it out.

 And want to keep the kids entertained without breaking the bank? Don’t forget to look for the deals link at the top of the calendar to filter for special offers and the free filter to see only free activities!

More Things To Do in Chicago This Week With Kids

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Best Things To Do This Weekend in Chicago With Kids

Millennium Park Holiday Sing-Along

Millennium Park- FREE
Friday, December 5
Sing together with other Chicagoans in this multi-cultural holiday event. A different performer will lead the sing-along each week at the Cloudgate sculpture. Songbooks will be distributed so participants can sing along. READ MORE

Live Holiday Caroling at the JW Marriott Chicago

Downtown- FREE
Friday, December 5
The holidays are magical in Chicago, and JW Marriott Chicago places guests at the center of it all. Step into the spirit of the season with complimentary live holiday caroling in the hotel’s grand lobby at 5 p.m. on Fridays, December 5, 12, and 19. Each 30-minute performance is open to guests and the public, filling the historic space with joyful harmonies, twinkling décor, and timeless holiday cheer. READ MORE

Fox River Trolley Polar Express

South Elgin
Friday, December 5- Sunday, December 7
Kids can relive the holiday classic book The Polar Express on this magical trip from the Fox River Trolley Museum. The train will go to the North Pole, where kids can meet Santa and receive a small gift. Each trip takes about one hour. READ MORE

Elf The Musical at the Auditorium Theater

South Loop
Opens Wednesday, December 3
Elf The Musical, inspired by the hit film, is the hilarious and heartwarming tale of Buddy, a young orphan child whose life is changed forever when he mistakenly crawls into Santa’s sack of toys one Christmas Eve. When he discovers he is human, Buddy embarks on a journey to New York City to find his birth father and, in turn, helps the Big Apple rediscover the true meaning of Christmas. READ MORE

Santa at the Driehaus Museum

Gold Coasat
Saturday, December 6
The Driehaus Museum hosts visits with Santa so kids can tell him if they are naughty or nice and take a selfie. New for this year! A professional photographer will be present to take your digital photo with Santa! In addition, on December 6th, families can explore our Drie-cember Market featuring seasonal treats, unique gifts, and festive kids’ activities. On December 13th, enjoy holiday music performed by talented students from Music Institute of Chicago from 9:30-11:30am. Tickets are required and are sold in 15 minute increments. READ MORE

Christmas Tree & Menorah Lighting Celebration at Mary Bartelme Park

West Loop- FREE
Saturday, December 6
Mary Bartelme Park hosts a Menorah Lighting Celebration, including live music, face painting, delicious snacks, and a children's story time! Santa will be on hand for pictures! READ MORE

Christmas Sing-along and Double Feature at the Music Box

Lakeview
Opens Saturday, December 6
Bring your family to see two holiday classics and sing holiday carols with Santa during intermission. Enjoy the double feature of It's a Wonderful Life and Irving Berlin's White Christmas. Santa will be accompanied by the Music Box organist while the lyrics are projected on the screen for everyone to join in the fun. READ MORE

The Beatrix Potter Holiday Party

West Loop
Opens Saturday, December 6
Four adorable Beatrix Potter favorites come to life in this mesmerizing, interactive trunk and puppet show, complete with original music. Storytellers weave Potter’s classic narration with gentle interactive moments, recruiting young watchers to join the adventure. After the show, head to the lobby to play with the puppets, take pictures with the cast, and join fellow Chicago families for a communal holiday party featuring a festive spread of holiday treats! Our stories this year will include  a brand new tale, “The Tale of Pickles and Ginger,” with “The Tale of Tom... READ MORE

Winterfest at Poplar Creek Country Club

Hoffman Estates- FREE
Saturday, December 6
Celebrate the holiday season with s'more making, ice-less skating, a gingerbread house making contest, sled dogs, stage shows, and more. Bundle up to stay warm in the cold. READ MORE

Hyde Park Holly-Day Celebration 2025

Hyde Park
Saturday, December 6
Sponsored by the University of Chicago, Hyde Park Holly-Day is back for 2025 with lots of FREE family holiday activities throughout Hyde Park on Saturday, December 6 at select times between 10 a.m. – 2 p.m. Don’t miss the ice carving demo & self-guided sculpture stroll, pictures with your favorite Santas, live reindeer & sleigh, free screening of “Zootopia 2", Buddy the Elf, costumed characters, dance performances, and holiday crafts. See you in Hyde Park! READ MORE

Santa's Jolly Jamboree

Lombard
Saturday, December 6
Santa's Jolly Jamboree is back! Make magical memories with the family as you visit Santa and gear up for the holiday season with a day of free, fun activities at Yorktown Center. READ MORE

Belle's Enchanted Holiday Tea Party

Portage Park
Saturday, December 6- Sunday, December 7
Step into the Portage Theater Fairytale Parlor for a refined holiday gathering inspired by Beauty and the Beast: The Enchanted Christmas. Your experience begins with holiday portraits with Belle, Ariel, and Cinderella, framed by warm candlelit décor and touches of wintry charm. Guests are then seated for a graceful tea service accompanied by an assortment of pastries and seasonal delights. READ MORE

Ravenswood Light-Up Night

Ravenswood- FREE
Saturday, December 6
Residents in the Ravenswood area light up their yards for the weekend before Christmas. With lights, disco balls, light-up figurines, and a selfie-station set up in the greenway, residents create a winter wonderland for visitors. Restaurants will feature specials for visitors. The event includes a scavenger hunt for kids, tree decorating contest, multimedia window, photo stations, and caroling. READ MORE

CASA Christmas Express

New Lenox
Saturday, December 6- Sunday, December 7
Ride the Polar Express from New Lenox to Tinley Park, where families can enjoy breakfast or lunch at Harald Viking Lodge. The event includes visits and photos with Santa, holiday cookies, activities throughout the day, and goody bags and souvenirs for children. Proceeds benefit Will and Grundy County children experiencing abuse or neglect. READ MORE

Tinley Park Parade of Lights

Tinley Park
Sunday, December 7
Festive floats, local businesses, community groups and school bands will march down Oak Park Avenue from 175th Street to the Subway parking lot. Special guests from the North Pole will make an appearance. READ MORE

2025 Clark Street Cookie Crawl

Lakeview
Sunday, December 7
Kick off the holiday season with sweet treats and festive fun at the Clark Street Cookie Crawl! Put on your coziest holiday pajamas or favorite holiday sweater and get set for a day of holiday cheer. Visit businesses along Clark Street to collect a variety of delicious holiday cookies. Enjoy surprises along the way including carolers, hot chocolate, and the chance to snap photos with Santa. It’s the perfect way to celebrate the season with family and friends! READ MORE

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