While some may want to escape to warmer climes during the cold months, others embrace the chill and the myriad activities associated with the season. For the latter group of people, Chicago is an excellent destination, particularly around the holidays, as the Windy City provides a multitude of opportunities to make a wonderland of winter. 


Christkindlmarket is a German Christmas market that takes place in Daley Plaza, as well as locations in Aurora and Wrigleyville. Based on the Christkindlesmarkt of Nuremberg, Germany (which dates back to the 16th century), this annual seasonal event is a relatively new tradition, having arisen in the mid-1990s as a means to promote bilateral trade between Germany and the United States.

This year, Christkindlmarket begins on Nov. 18 and lasts until Dec. 24. There are few better places to get your holiday shopping done, so come ready to stock up on loads of traditional handmade creations, including ornaments, clothing accessories, handicrafts, cakes, and mulled wine.

Address: Daley Plaza, 50 W. Washington St., Chicago, IL 60602.

Time: The market’s general hours of operation vary by day. Sunday–Thursday hours are 11 a.m.–8 p.m., while Friday–Saturday hours are 11 a.m.–9 p.m. On Thanksgiving (Nov. 24) and Christmas Eve (Dec. 24), the market operates from 11 a.m. to 4 p.m.

Contact: Send questions and comments to info@christkindlmarket.com or call 312-494–2175.

Ice-Skating at Maggie Daley Park

Ice-skating and Christmas is a classic pairing, and one of the best places to strap on a pair of blades is the ice-skating ribbon at Maggie Daley Park. The ribbon is a quarter-mile strip of ice that twists and curves through the park. Bundle up and feel transported from the city to what appears like an Alpine landscape.

The ribbon opens to the public on Nov. 19. You can, of course, skate with your own ice skates, but rentals are available as well. Aside from the cost of renting, admission is totally free, but bear in mind that you must make reservations at least 72 hours before the date on which you’d like to skate.

Address: 337 E. Randolph St., Chicago, IL 60601.

Time: Once the ribbon opens, it operates seven days a week, 11 a.m.–10 p.m.

Contact: You can direct general inquiries about the park to info@maggiedaleypark.com. For concerns relating specifically to the ice ribbon, call 312-552-3000.

Holiday Tree Lighting at Millennium Park

Every year, the city of Chicago puts up a massive holiday tree in Millennium Park, and the lighting ceremony is an iconic winter attraction. The tradition began in 1913, conceived by the Municipal Christmas Festival Association. That first ceremony took place at 6 p.m. on Dec. 24 of that year. Around 600 multicolored bulbs adorned a 35-foot spruce tree, which then-Mayor Harrison illuminated with the press of a button.

This year marks the 109th annual lighting of the holiday tree. These days, the ceremony typically takes place in mid-November, and the tree remains lit into January. The event is free to attend.

Address: 201 E. Randolph St., Chicago, IL 60601.

Time: Information concerning the holiday tree lighting will become available as winter draws nearer.

Contact: If you have any questions, try contacting the Millennium Park Foundation via online inquiry. You might also try calling City Hall at 312-744-5000 (from outside of Chicago) or 311 (from within Chicago).

Christmas Around the World and Holidays of Light at the Museum of Science and Industry

Another winter holiday tradition in Chicago is the Christmas Around the World and Holidays of Light exhibit at the Museum of Science and Industry. This tradition dates back to 1942, when the exhibition featured just one tree. Nowadays, it involves a virtual forest of more than 50 arboreal specimens along with decorated displays and a four-story Grand Tree, all for the purpose of showcasing different cultural holiday traditions.

For 2022, the exhibit will follow a travel theme, incorporating the museum’s displays of the Pioneer Zephyr train and the Boeing 727 in its Take Flight exhibit. You can purchase advance tickets online. Admission is $21.95 for adults (12 years old and up) and $12.95 for children (ages 3 to 11).

Address: 5700 S. DuSable Lake Shore Drive, Chicago, IL 60637.

Time: The Museum of Science and Industry is open daily from 9:30 a.m. to 4 p.m. Note that there are certain exceptions to these hours during the winter season. The museum will have extended hours until 5:30 p.m. on Nov. 23 and 25 as well as Dec. 4, 11, 23, and 26–30. It will be closed, however, on Thanksgiving (Nov. 24) and Christmas (Dec. 25).

Contact: Use the museum’s contact page to submit inquiries online, or call 773-684-1414.

Dining at the Walnut Room

The Walnut Room is a restaurant occupying the seventh floor of the Macy’s department store in downtown Chicago. The building opened in 1907, when it went by the name Marshall Field & Co. A milliner associate named Mrs. Hering, realizing that she was losing out on sales when shoppers left at noon to have lunch at home, began selling her own dishes as a strategy to retain customers. Thus began the first-ever restaurant to operate within a department store. One of the most popular dishes in those years was Mrs. Hering’s chicken pot pie.

Dining at the Walnut Room has become a Christmas tradition thanks to the addition of the Great Tree, which stands 45 feet tall and hangs from the ceiling. As for the food, you have an all-you-can-eat buffet, a tremendous spread that includes more than 16 dishes, plus desserts. Among those dishes are miniature versions of Mrs. Hering’s original chicken pot pie. The buffet runs $30 per adult and $11 per child under 12 years old. Children under 12 months of age eat for free.

Address: 111 N. State St., Chicago, IL 60602.

Time: The Walnut Room is open seven days a week. Sunday–Tuesday hours are 11 a.m.–3 p.m. Wednesday–Saturday hours are 11 a.m.–7 p.m. 

Contact: Call 312-781-5219 for reservations. Holiday reservations open on Oct. 1.

There you have our recommendations for the best winter holiday attractions in Chicago. Before you head out for the holidays, consider updating your auto insurance with us. We provide numerous coverage options to ensure that you remain protected on your road travels. Call us at 800-483-4868 or use our online inquiry form to get a free quote today. Our agents are available six days a week — Monday–Friday from 8 a.m. to 8 p.m. and Saturday from 8 a.m. to 5 p.m. — and look forward to helping you get the coverage you need.


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