Christmas in Chicago, Illinois is quite possibly the best time to visit this magnificent, family-friendly city. From November through December, there is always something, fun, free and festive going on to celebrate Christmas in Chicago.  From the millions of tiny bright lights, holiday markets and nostalgic ice skating at Millennium Park, the warmth of Christmas prevails over the chilly Chicago air.  These 11 festive things to do during Christmas in Chicago that will leave your whole family feeling merry and bright.

My husband and I, along with our three boys, had the delightful opportunity to visit Chicago last December. We were so touched by the festive atmosphere that we decided to go back again this year and attend the Tree Lighting Parade.

Chicago has so many events and activities during the holiday season. Here are some ways to warm your heart in the Windy City.

1. Christmas Tree Lighting Ceremony

Consider starting off Christmas in Chicago by attending the annual Christmas tree lighting ceremony held at Millennium Park.  For the past 106 years, guests to Chicago gather around a gigantic 60-foot evergreen to watch the lights being switched on in celebration of a new holiday season. This free, family-friendly event takes place at Millennium Park’s Wrigley Square and includes live carolers and musical performances.

The park festivities begin at 6 p.m. on November 22, with the official tree lighting following at 6:30 p.m.  Plan to arrive early for this is a hugely popular event.

2. The Magnificent Mile Lights Festival and Tree-Lighting Parade

Christmas in Chicago continues with a two-day festival in the upscale shopping district of Magnificent Mile. With Mickey and Minnie Mouse as the grand marshals, a holiday parade captivates both kids and adults with gigantic floats and huge helium balloon figures. In addition, the dozens of trees outlining the 13 city-block stretch of Magnificent Mile light up one-by-one as the parade goes by.  This free event draws national publicity and huge crowds as Santa Claus makes his way through the city streets.

The 2019 Magnificent Mile Lights Festival starts at 4:00 p.m. on Friday, November 22 and runs through the evening of Saturday, November 23.  The tree lighting parade makes it way down Michigan Avenue on Saturday, November 23 from 5:30 to 7:00 p.m.  Fireworks take place over the Chicago River at North Michigan Avenue at 6:55 p.m.

3. Zoolights at Lincoln Park Zoo

For the past 25 years, Lincoln Park Zoo has offered yet another free, festive holiday celebration in the heart of downtown Chicago. One of the only free zoos remaining in the country, Lincoln Park Zoo is transformed into a lighted masterpiece featuring 2.5 million lights during Christmas in Chicago.

The gigantic 3D light displays, musical light shows, live ice carvings, and strolling carolers create a true winter wonderland. There are several ticketed experiences, including a gigantic 65-foot Ferris wheel and light maze. Zoolights is a fantastic holiday activity for toddlers and teens alike!

Zoolights opens on Friday, November 29 at 4:25 p.m. and runs through Sunday, January 25 at 9:00 p.m. Consider spending Zoo Year’s Eve among the Zoolights on December 31 as Lincoln Park hosts Chicago’s biggest adult-only New Year’s Eve party.

4. Winter Wonderfest at Navy Pier

December 6 through January 12, Chicago’s historic Navy Pier will be transformed into Winter Wonderfest. Winter Wonderfest is a fabulous way to celebrate Christmas in Chicago, as it includes over 170,000 square feet of indoor rides, slides, attractions, and indoor ice skating. This beloved family tradition is a ticketed event; crowds are exceptionally large on the weekends all throughout December.

All attendees 36″ and up must have a paid ticket that can either be purchased online prior to arrival, or at the festival box office.  Tickets go on sale starting on November 6th, 2019.

5. Caroling at Cloud Gate

Fridays from 6-7 p.m. from November 29 through December 20, stop by Cloud Gate (otherwise known as “The Bean”). Each week, a different local choir leads classic Christmas caroling. This annual event is one of the most heartwarming Christmas experiences, as literally hundreds of people come together to sing in unison in front of Chicago’s most iconic sculpture. (Visiting The Bean itself is one of the best free things to do in Chicago.)

This free event is appropriate for all ages. I recommend caroling at Cloud Gate to anyone looking for a festive thing to do to celebrate Christmas in Chicago.

6. Christkindlmarket Chicago

A holiday tradition since 1996, Chirstkindlmarket is one of our favorite festive activities when we celebrate Christmas in Chicago. Vendors from all over the world come together to sell German-inspired food, drinks, and holiday gifts in this massive outdoor mini village. From handmade items like knit hats and cuckoo clocks, to foods like strudel and sausage, the sights and smells of Chirstkindlemarket fill my dreams months after Christmas is over.

Held November 15 through December 24 at Daley Plaza, Christkindlemarket is rich in warm German tradition and flair. It is very crowded and busy here, especially in the evenings, so this may not be the best activity for little ones.

7. Ice Skating at Millennium Park

One of our favorite festive things to do during Christmas in Chicago is to skate under the Chicago skyline at Millennium Park! Within viewing distance of the great Chicago Christmas tree, the Millennium Park ice skating rink is a classic take on family-friendly holiday fun! Don’t know how to skate?  Free ice skating lessons are offered on Fridays at 11 a.m. and Saturdays and Sundays at 9 a.m.

Ice skating at Millennium Park is open to the public from mid-November through March, weather permitting.  Admission is free and skates can be rented for $13 Monday-Thursday, or $15 Friday-Sunday.

8. Christmas Around the World at the Museum of Science and Industry

Perhaps one of the most festive things to do during your Christmas Chicago itinerary is to attend the Christmas Around the World display. Beginning November 14, 2019, Chicago’s famed Museum of Science and Industry transforms its giant rotunda into a forest of perfectly decorated Christmas trees. With the 45-foot Grand Tree in the center, more than 50 trees and holiday displays represent different cultures and traditions from around the globe.

Perfect for families and children of all ages. Visitors have until January 5 to experience this one-of-a-kind event. Admission is included in the museum entry fee of $19.95 for adults, and $10.95 children ages 3-11.

9. The Great Tree at Macy’s Walnut Room 

Visiting Macy’s on State Street is a nostalgic and festive addition to your Christmas in Chicago experience. Start by admiring the gigantic holiday window displays outside of Macy’s before making your way into the department store. Stop for a visit with Santa at Santa Land. Then dine in the historic Walnut Room adorned by a giant 60-foot Christmas tree. Watch out for fairies! A costumed fairy visits each table and grants wishes. She sprinkles fairy dust and gives out little marbles from the North Pole.

To view the Great Tree, visit Macy’s during operation hours Saturday, November 3 through Sunday, January 6. Likewise, visit macyrestaurants.com to schedule dining reservations in the Walnut Room. You may join the Walnut Room wait list on the day of your arrival, but doing so can result in a wait of up to three hours.

10. Holiday Shopping

What is more festive than holiday shopping? Holiday shopping in Chicago is a fun and fascinating experience, as there is literally a little bit of everything here. Chicago’s Magnificent Mile includes shops like Gucci, Louis Vuitton, Chanel, Burberry, and Neiman Marcus. It’s the Midwest’s equivalent to Beverly Hills’ Rodeo Drive or New York’s 5th Avenue! Kid-friendly stops include the Disney Store and American Girl Place

Neighborhoods like Lincoln Square, Andersonville, or Bucktown offer more eclectic boutique finds for a truly one-of-a-kind gift.

11. Holiday Tours

One of the best ways to experience Chicago at Christmas is to take part in one of its many holiday tours.  All of Chicago’s private transportation companies get into the holiday spirit by offering special tours to experience the best of Chicago’s activities and lights. From winter walking tours and holiday dinner cruises to sky-high views from a Chicago Helicopter Experience, the holiday tour options are endless. My personal favorite is the Holiday Lights Tour through Chicago Trolley. It hits all of the Christmas hot spots like Macy’s, Chirstkindlmarket, and Lincoln Park Zoo.

No matter which of these festive things you choose to do during Christmas in Chicago, incredible memories are ready to be made.  Come and discover why Christmas in Chicago is truly the most wonderful time of the year!