Near South Side Other Christmas Activities 2026

Lace up your running shoes for the Chicago Santa Hustle, a festive race event on December 5, 2026, at Soldier Field. Choose from a 5K, 10K, or a fun Kids Dash. Participants receive exclusive holiday-themed apparel and a commemorative finisher...

All aboard for holiday cheer! Chicago's beloved Allstate CTA Holiday Train and Bus return, bringing festive magic to the city. Ride the dazzling train, adorned with thousands of lights and featuring Santa and his reindeer, or hop on the decorated...

Join the city of Chicago for the 113th Annual Christmas Tree Lighting Ceremony in Millennium Park. This beloved tradition kicks off the holiday season with the illumination of the city's official Christmas tree. The event features live entertainment, seasonal treats,...

Experience a unique holiday event with filmmaker John Waters at Avondale Music Hall. This special Christmas show promises his signature blend of humor and unconventional holiday cheer, offering a one-of-a-kind festive experience.

Gather at Millennium Park's Cloud Gate for a heartwarming Holiday Sing-Along. On select Fridays in December, Chicagoans and visitors are invited to join in a joyous celebration of diverse holiday traditions. Sing along to classic carols with provided songbooks, featuring...

Experience the magic of the holidays with a special visit to Santa at 900 North Michigan Shops. This festive event features a beautifully decorated winter wonderland, complete with a towering Christmas tree and a charming vintage sleigh. Visitors can reserve...

Celebrate the start of the holiday season at West Chicago's annual Frosty Fest. This beloved community event features a magical tree lighting ceremony, opportunities to meet Santa and Mrs. Claus, and a festive Elves Workshop for unique gift shopping. Enjoy...

Join the iconic Chicagoland Toys For Tots Motorcycle Parade, the world's largest of its kind, dedicated to bringing holiday joy to children. This massive event encourages participants to donate a toy, with all proceeds and merchandise sales supporting parade expenses...

Wintrust Winter WonderFest transforms Navy Pier into an indoor holiday event with ice skating, rides, and the Centennial Wheel in a decorated setting.

Santa at 900 North Michigan Shops provides professional photos in a winter wonderland setting with a tree and digital displays. Each reservation includes a plush toy and digital photo.

Winston Plaza hosts Santa's arrival by helicopter on Saturday, November 14th, 2026, at noon. The event includes a magic show, face painting, and children's crafts. A free photo with Santa is available with a $25+ purchase from a merchant.

An evergreen wreath-making workshop teaches participants to craft a wreath for holiday decorating. All materials are included. The workshop is for adults seeking to personalize their holiday decor.

Adults over 60 can take a day trip to Shipshewana, Indiana, including the Ship Chic Holiday Craft Show, lunch at an Amish home, downtown exploration, and the 'Lights of Joy' drive-through light show.

Families can assemble and decorate a gingerbread house using a kit, icing, and sweet treats, followed by playtime at the Exploritorium.

Discover a day of intergenerational cultural fun at the Chicago Cultural Center's Holiday Open House. This free event features a variety of activities for all ages, including live music and dance performances, hands-on art workshops, and engaging exhibitions. Explore the...

Unleash creativity at Glazed Expressions by decorating a unique menorah, perfect for a cherished Hanukkah keepsake. This engaging event is designed for children of all ages to enjoy, with delightful snacks and drinks provided to enhance the festive experience.

Capture the magic of Christmas at the North Pole with this enchanting floral arrangement. Featuring a hand-painted, lighted cottage inspired by Thomas Kinkade, it depicts Santa and his elves preparing for their big night. Nestled amongst lush red roses and...

Join the festive spirit at Hamilton Park for a delightful holiday event featuring Santa Claus and his friends. This celebration promises an afternoon filled with joy, including toys, delicious desserts, engaging music, lively dance performances, and creative arts and crafts....

Experience the magic of the holidays as Santa Claus makes a special visit to North Berwyn in his mobile workshop. This unique event offers residents the chance to receive a personal meet-and-greet with Santa right at their home, perfect for...

Step into a winter wonderland at the Forest Park Holiday Walk! Stroll down Madison Street to discover enchanting live window displays and enjoy open houses at local shops. Delight in magical horse-drawn sleigh rides, marvel at a festive ice sculpture,...

Children can send their heartfelt letters to Santa Claus and receive a special response. This free event is open to all ages, encouraging young ones to share their holiday wishes and good deeds. A dedicated mailbox ensures their letters reach...

Join the Johnson-Phelps VFW Post #5220 for their annual Christmas Party! This festive event promises an afternoon of holiday cheer. Keep an eye out, as Santa and Mrs. Claus are rumored to make a special appearance, bringing extra magic to...

Celebrate the Festival of Lights with a variety of Hanukkah events happening throughout Chicagoland in 2025. Families can enjoy hands-on activities like Menorah decorating and craft workshops, along with festive celebrations featuring games, music, and storytelling. These events offer a...

The Drake Hotel in Chicago transforms into a festive wonderland for the holidays, continuing a tradition of over 100 years. Guests can enjoy elegant afternoon teas, including the special 'Festival of Lights' tea, and festive dining options like Thanksgiving and...