Fun and Free: Winter Holiday Events in Chicago for Your Family

Photo Courtesy of Choose Chicago

Recently, Chicago was named the best big city in America by the Condé Nast Traveler Readers’ Choice Awards…again for the 10th year in a row! And during the winter holidays, Chicago really proves why it is the best. Our city shines with festive parades, cherished annual traditions, and glittering spectacles across the city. As Choose Chicago points out: “Like a holiday storybook come to life, winter in Chicago turns ordinary moments into joyful celebrations.”

“Join the fun and embrace the season’s magic that makes Chicago feel warm and bright, even on the chilliest days.” Here are a few of the top free family-friendly winter holiday events and traditions in Chicago.

• Chicago Christmas Tree in Millennium Park
  • What it is: The official city holiday tree lit up for the season near Michigan Avenue and Washington Street.
  • When: Late November through early January.
  • Cost: Free admission to view and walk around.

  https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park_tree.html

• Christkindlmarket Chicago at Daley Plaza
  • What it is: An authentic open-air German-style Christmas market featuring wooden vendor huts, festive music, and holiday displays.
  • When: Late November through December 24.
  • Cost: Free admission (food, drinks, and souvenirs cost extra).

  https://www.christkindlmarket.com/daleyplaza/

• Lincoln Park ZooLights (Free Mondays)
  • What it is: Millions of dazzling LED lights, animated displays, and seasonal music spread across the zoo grounds.
  • When: Late November through early January.
  • Cost: Free on designated Monday evenings (advance registration required), nominal fee on other nights.

  https://www.lpzoo.org/event/zoolights/

• Millennium Park Holiday Sing-Along
  • What it is: A multi-cultural community caroling and singing event led by local choirs and guest performers near the Cloud Gate (“The Bean”) sculpture.
  • When: Select Friday evenings in December.
  • Cost: Free (songbooks provided on-site).

  https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park_sing_along.html

• Holiday Windows at Macy’s on State Street
  • What it is: Elaborate, animated holiday window displays telling classic seasonal stories along the store’s historic street-level facade.
  • When: Late November through early January.
  • Cost: Free to view from the street.

  https://www.macys.com/s/holiday-celebrations/

• Winter Flower Show at Garfield Park Conservatory
  • What it is: An indoor tropical escape featuring a vibrant seasonal floral display filled with colorful poinsettias and festive greenery.
  • When: Daily from late November through early January.
  • Cost: Free (though online advance reservations are required).

  https://www.chicagoparkdistrict.com/conservatory-flower-shows

• Art on the MART
  • What it is: The world’s largest permanent digital art projection, which frequently features special winter and holiday-themed light displays projected onto the 2.5-acre river-facing facade of the Merchandise Mart.
  • When: Evening hours through December.
  • Cost: Free to view from the Chicago Riverwalk (best viewing from Wacker Drive between Wells and Ross St.).

  https://artonthemart.com/