The Chicago holiday season roars into gear with the 90th annual Chicago Thanksgiving Parade, which marches down the heart of downtown on State Street on November 27, 2025. This free family-friendly event is highly anticipated because of the exciting showcase of talented performers from … [Read more...] about Chicago Thanksgiving Parade
Holidays
Winterland at Gallagher Way
Dive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, 2025. Head to the Wrigleyville neighborhood to … [Read more...] about Winterland at Gallagher Way
Chicago’s Christkindlmarket
You don't need to travel to visit a charming European Christmas market because Chicago hosts the most authentic European holiday market outside of Europe. Christkindlmarket brings the sights, scents and sounds of a German holiday market to Chicago, opening on November 21, … [Read more...] about Chicago’s Christkindlmarket
Chicago Magnificent Mile Lights Festival
Chicago's iconic Michigan Avenue will shine even brighter during the 31st annual Magnificent Mile Lights Festival on November 22, 2025. This beloved holiday tradition combines a parade, lights, music, tree lighting and family activities for joy-filled holiday fun. The event kicks off at … [Read more...] about Chicago Magnificent Mile Lights Festival
Millennium Park Holiday Tree Lighting
The beloved Chicago holiday tradition of lighting the Christmas tree that towers over Millennium Park will kick off on November 21, 2025. This live event will fill Millennium Park with music, fireworks and thousands of twinkling lights. A 53-foot-tall Colorado blue spruce was selected for … [Read more...] about Millennium Park Holiday Tree Lighting
Maggie Daley Park Skating Ribbon
Whirl around the twirling ice skating ribbon at Maggie Daley Park for the ultimate winter season experience. The Maggie Daley Park Ice Skating Ribbon is open every day from November 14, 2025, through March 8, 2026. Roll around the whimsical ice skating ribbon for a more exciting ride than … [Read more...] about Maggie Daley Park Skating Ribbon
Free National Museum of Mexican Art Dia de los Muertos Chicago
Celebrate the Mexican tradition of Dia de los Muertos or Day of the Dead with the free "Dia de Los Muertos Xicago" event organized by the National Museum of Mexican Art on October 25, 2025, in the Pilsen community. Honoring loved ones who have passed away with ofrendas or altars filled with … [Read more...] about Free National Museum of Mexican Art Dia de los Muertos Chicago
Cheap Things to do in Chicago on New Year’s Eve
New Year's Eve in Chicago offers all the glamor and excitement expected on the last day of the year but all that glitz comes at a price. New Year's Eve events are notoriously expensive, whether you're just toasting the holiday with champagne or dancing the night away. If you don't … [Read more...] about Cheap Things to do in Chicago on New Year’s Eve
Chi-Village Kwanzaa Celebration
The exuberant seven-day African American tradition of Kwanzaa will be celebrated with eight hours of free music, dance, workshops and presentations by Chi-Village in the Roseland community on December 26, 2024. The second annual Chi-Village Kwanzaa Celebration weaves the past and … [Read more...] about Chi-Village Kwanzaa Celebration
Handmade Market at Empty Bottle
Head to a classic Chicago tradition to supply your shopping for the holidays and beyond at Handmade Market at the Empty Bottle. This month's market opens on December 14, 2024, but the market returns on the second Saturday of the month through April 2025. Handmade Market connects the makers of … [Read more...] about Handmade Market at Empty Bottle
St. Lucia Festival of Lights
Celebrate the beautiful Swedish tradition of St. Lucia Day at the Swedish American Museum in the Andersonville neighborhood. The annual candlelit procession down Clark Street will take place on December 13, 2024. Starting at sunset around 4:45 pm, specially selected St. Lucia girls" wearing long … [Read more...] about St. Lucia Festival of Lights
Skate in the Clouds at Peninsula Sky Rink
Ice skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with sparkling lights and pine trees. The rink is open through February 2, 2025. Ride up to the … [Read more...] about Skate in the Clouds at Peninsula Sky Rink
