6 Festive Holiday Events Around Chicago

2021 Chicago Holiday EventsAs fall starts blending into winter, some of the most important holidays begin to peek their heads around the corner.  Thanksgiving, Christmas, and Hanukkah, to name a few, mean family time and endless celebrations.  With spending time together for the holidays is even more possible this year.  


This special event is one of Chicago’s most renowned Christmas attractions.  This year marks the 25th anniversary of the winter market, which brings inevitable surprises to the table.  

Starting on November 19th to the end of December, the market will adorn the courtyard of Daley Plaza in lights and Christmas wreaths.  The event connects German and Austrian traditions and draws inspiration from the Nuremberg original.  Watch the modern era melt around you with this 16th-century winter wonderland. 

For the 25th anniversary, another market will be open in Wrigleyville.  It’ll have all of the usual market components: fresh pretzels, mulled wine, and festive music.  Wherever you are on the north side, Christkindlmart is the perfect visit for igniting the Christmas spirit.  Check out more details here: https://www.christkindlmarket.com/ 

Zoo Lights

Lincoln Park Zoo is truly the place to be this holiday season.  The gorgeous lights hung up in the park create a spectacle, unlike anything in Chicago.  

Just like in years past, thousands of LED lights will dance along the perimeter of the park.  Guests can walk through the zoo taking photos, enjoying cocktails, and eating festive treats.  The displays cost a minuscule $5 for entry, but Monday and Tuesday night’s admission is free.  

More details about Lincoln Park’s Zoo Lights are on the park website: https://www.lpzoo.org/event/zoolights-presented-by-comed-and-invesco-qqq/ 

Millennium Park Sing-Along 

Okay, so you’ve visited The Bean before.  But have you ever experienced hundreds of people singing around Chicago’s most iconic structure? 

This year, Millennium Park is hosting a plethora of winter concerts to awaken the singer in all of us.  Previously known as Caroling at Cloud Gate, the new-and-improved event incorporates songs from multiple faiths and nations. If you’re unfamiliar with the songs, no worries; A songbook will be distributed to each participant to ensure your choir experience is immaculate. The fest will begin November 26th and continue through December every Friday at 6 pm.     

Check out more about this sing-along here: https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park13.html 

Ice Skating in the Park 

Millennium Park has many festive attractions to offer, but the ice skating is genuinely superb.  With two different rinks to choose from, skating downtown has never been more accessible.  

The McCormick Tribune ice skating rink is your classic go-to rink.  The picturesque landscape of The Loop makes for the perfect backdrop.  With reservations needed for entry, this spot behind the Bean ensures minimal overcrowding on the rink.  

If you want to skate away from the hustle and bustle, Maggie Daley Park is another beautiful choice.  Its shape is more unusual, with winding turns that spread out along Millenium Park.  It’s twice as long as a regular rink, optimal for spreading out and trying some moves.  

Book your reservations here:  https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park10.html 

Light Up The Lake at Navy Pier 

The brand new holiday attraction is coming to Chicago’s favorite pier.  Humungous sculptures with more than 600,000 lights comprise most of the 2021 features.  The attraction includes an ice rink, a holiday beer garden, train rides, and other activities.  

The luminescent garden begins at the end of October and will last throughout the holiday season.  Stay up to date with the Light Up The Lake event here: https://navypier.org/ 

Holiday Movies at Gallagher Way 

Adjacent to the major stadium Wrigley Field lies another space for entertainment and fun.  Gallagher Way is an urban park with local businesses, outdoor seating, and beautiful green space.  Following covid procedures from last year, Gallagher Way will show outdoor movies to celebrate the holidays safely.  

Some of the most classic holiday films are on the roster this year.  Home Alone, A Christmas Story, and Elf are being projected each weekend in December.  The list of movies hasn’t been updated completely, so check up on the Gallagher website for more film news: ​​https://winterland.gallagherway.com/ 

The holidays are always a splendid time in Chicago.  Lucky for us, this year is full of numerous events to attend.  If you’re excited about celebrating the season, consult this list for the best holiday-inspired events.