The holiday season is here! Discover festive events to celebrate all across the area, from charming holiday markets to dazzling winter light displays. With so many ways to soak up the magic of this special time of year, here are a few of our top picks for this weekend.
Explore Winterland
It’s opening day at Gallagher Way’s Winterland! Start with their Tree Lighting Ceremony, then take a ride on the Holiday Train around Winterland or challenge your friends and family at the Winterland Bumper Cars. Enjoy live music, seasonal food and drinks, and holiday décor and photo opportunities with Santa. While this is just opening day, Winterland will run until December 21, offering plenty of time to soak in the holiday cheer.
Date: December 6
Time: 4PM-9PM
Cost: Free
Location: Gallagher Way, 3635 N Clark St
More Info: gallagherway.com
Find Magic at the One of a Kind Show
Celebrate the 23rd year of the One of a Kind Show, featuring 600 exceptional artists, designers, and makers. This event showcases thousands of handmade products across 20 categories, including jewelry, pet products, home goods, and more. It’s the perfect place to find unique, handcrafted gifts and support talented creators. Explore the creativity and craftsmanship of these artisans and discover one-of-a-kind pieces to gift to your loved ones this holiday season.
Date: December 6-8
Time: Fri & Sat 10AM-7PM; Sun 10AM-5PM
Cost: $15+
Location: The Mart, 222 W Merchandise Mart Plaza
More Info: oneofakindshowchicago.com
Go on a Winter Walk on Wilson
Join the Uptown community for the Winter Walk on Wilson, an event filled with treats, warm drinks, and menu samples from local businesses and organizations. Enjoy live holiday music and caroling, large-scale puppets and objects, a pop-up holiday market, and photo ops with Uptown’s own Panda Claus! To celebrate 10 years of this event, the Uptown Chamber will also be awarding prizes to a select few who RSVP for this event.
Date: December 6
Time: 5PM-8:30PM
Cost: Free
Location: W Wilson Ave and N Broadway
More Info: partners.exploreuptown.org
Make a Difference at Run, Donate, Spead Joy: 5K for Toys!
This event starts and ends at Mandala Cafe, where participants are encouraged to bring a new, unwrapped toy to donate. All collected toys will go to the Pilsen Food Pantry, helping to bring joy to families this holiday season. After the run, gather at Mandala Cafe for refreshments. Not a runner? Stop by to support and donate.
Date: December 8
Time: 9AM-11PM
Cost: Donate a Toy to Participate
Location: Mandala Café, 1641 W 18th St
More Info: eventbrite.com
Celebrate at the Hyde Park Holly-Day
Celebrate the holidays across various locations in Hyde Park during Hyde Park Holly-Day. At Harper Court, watch an ice carving demo and test your skills at their ice-skating rink. Stop by Harper Theater to watch a free movie screening of ‘Moana 2’. Visit the Promontory for photos with Soul Santa and Mrs. Claus, holiday crafts, book giveaways, and dance performances. This event Is packed with activities and offers something for everyone.
Date: December 7
Time: 10AM-5PM
Cost: Free
Location: Various Locations
More Info: hphollyday.com
