Near South Side Other Christmas Activities 2026

Participants can run or walk through 5K and 10K courses lined with cheerful volunteers and aid stations, while children up to age 12 can participate in a 1K Kids Dash. Entrants receive themed apparel including beanies or Santa hats and...

Visitors gather in viewing areas throughout the park equipped with giant screens to watch the official illumination of the city's Christmas tree. A vibrant main stage along Washington Street next to the Chicago Cultural Center hosts seasonal entertainment, accompanied by...

Navy Pier transforms into an indoor holiday destination filled with festive décor and seasonal attractions for visitors of all ages. Guests can take to the ice on the rink, with ice skating included with entry. Visitors can also experience the...

Visitors gather at Cloud Gate, also known as The Bean, to celebrate Chicago's diverse holiday traditions through choral music and communal singing. Attendees can follow along using printed songbooks or digital downloads to join their voices together. The program also...

Santa lands by helicopter at the shopping center to kick off family holiday activities. Visitors can watch a magic show, participate in face painting and kids crafts, and take photos with Santa with a qualifying merchant receipt.

Participants travel by coach bus to Shipshewana, Indiana, to explore the Ship Chic Holiday Craft Show and spend free time in the downtown area. The trip includes a homemade lunch at an Amish residence. Guests also experience Lights of Joy,...

Guests attend a live seated holiday show featuring John Waters. The performance takes place inside the Avondale Music Hall with both general seated admission and VIP options available.

Children and families can bring their letters for Santa to a magical mailbox at the park gazebo. Visitors get to meet one of Santa's elves to make sure their letters are safely on their way to the North Pole. Guests...

Participants learn hands-on techniques for crafting a beautiful evergreen wreath. Everyone creates and takes home a completed winter decoration ready to display. All required materials are provided.

Families work together to assemble and decorate their own gingerbread house using supplied icing and an assortment of sweet treats. After crafting their holiday creations, participants can head over to enjoy playtime in the Exploritorium.

Participants build artisan gingerbread houses using handmade frosting and decorate them with an array of candies, cookies, and goodies. Guests can enjoy unlimited non-alcoholic beverages such as espresso, coffee, hot chocolate, hot cider, or a signature mocktail alongside light savory...

Grandparents and grandchildren gather for a festive holiday celebration centered around creativity and sweet treats. Participants decorate an assortment of holiday cookies using colorful frosting, sprinkles, and festive decorations. Everyone leaves with their custom holiday creations to take home.

Participants gather to discuss the holiday cozy mystery novel The Most Wonderful Crime of the Year by Ally Carter. The club features a meet-and-greet session where attendees make a bookmark, learn how to access the book, and enjoy appetizers and...

Ring in the new year with a holiday-themed public ice skate. The event welcomes participants of all ages to take to the ice at Centennial Ice Rinks.

Participants enjoy private ice time featuring photo opportunities with Santa, holiday music, and hot chocolate. A skating trainer device is available to assist children who are new to the ice. Skate rental is provided for each registered participant.

Families sip hot chocolate and enjoy fresh donuts provided by Naperville's DeEtta's Bakery. Children can listen to a holiday story told by Santa and take pictures with him.

Families gather for an evening of festive holiday activities at the Dellwood Park Community Center. Guests can visit with Santa, enjoy inflatable fun, and make a holiday craft. The event also includes pizza and hot chocolate.

Visitors can join in a festive indoor swim with Santa at Challenge Fitness. The seasonal event is organized by the Lockport Township Park District at their local community fitness and aquatics facility.

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 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...

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...

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,...

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...

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.

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...

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.

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...

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...