11 Things to Do This Chilly Weekend in Chicago

There are plenty of ways to spend your weekend, whether your ready to get festive or you just want to get out on the town

The holiday season has begun in Chicago and there are plenty of ways to spend your weekend, whether your ready to get festive or you just want to get out on the town. 


Bundle up and join the crowd at Chicago’s downtown Christkindlmarket. Delight in hot chocolate or glühwein and celebrate the return of the iconic boot-shaped mug. The popular festival will continue through Christmas Eve in Daley Plaza with free admission. The market will close early on Thanksgiving Day (Nov. 28) and Christmas Eve (Dec. 24) at 4 p.m.

When: Nov. 15-New Year's Eve

Sunday – Thursday: 11 a.m. – 8 p.m.

Friday – Saturday: 11 a.m. – 9 p.m.

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

Millennium Park Ice Skating

Grab your skates – or rent them at the park – and head to Millennium Park to enjoy this winter season with outdoor fun. The park offers free skating classes for all ages and skill levels at 11 a.m. on Fridays and at 9 a.m. on Saturday and Sunday. Rentals are $13 on weekdays and $15 Friday through Sunday.

When: Nov. 15 at 12 p.m.

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

Turkey Trot at Rainey

Put on your running shoes and bundle up this weekend for the Turkey Trot in the park. Registration for the event begins at 8 a.m. and the race starts at 9 a.m. with a $5.00 fee. The event is open for all ages, but participation is for children 6 and up.

When: 8 a.m. to 12 p.m. on Nov. 16

Where: Rainey (Edward) Park, 4350 W. 79th St. Chicago, IL, 60652 

Cool Weather Camping Clinic at NPV

Acquire hands-on camping skills this winter with the North Park Village Nature Preserve and your friends and family this weekend. Build a campfire, pitch a tent, brew hot coffee and hot chocolate, and much more. This event is free, and all supplies for the activities will be provided by NVP. You must be 13 and older to participate and register at before attending. Space is limited.

When: 1- 2:30 p.m. on Nov. 16

Where: North Park Village Nature Center Park, 5801 N. Pulaski Rd., Chicago, IL, 60646 

Super Seed at NPV

Register your little ones to help collect and plant seeds at the NPV preserve for next spring. Children between 3 to 6 years old are welcome in this drop-off program. Participants must be toilet trained and must register at before attending. This event is free.

When: 1-2 p.m. on Nov. 16

Where: NPV Nature Center Park, 5801 N. Pulaski Rd., Chicago, IL 60646 

Saturday Night Standup Comedy at Laugh Factory Chicago

Join the Laugh Factory for a night filled with laughter and positivity with the "greatest lineup of standup comedy in the city." Attendees must be 18 and older and must RSVP for free admission. There is a two-drink minimum per person, which can be an alcoholic or non-alcoholic beverage.

When: Every Saturday from Nov. 16 – Dec. 21, 7 – 9:30 p.m. 

Where: 3175 North Broadway, Chicago, IL, 60657

Wrigleyville Brunch Crawl at Gallagher Way

Expand your palate at Gallagher Way with a variety of food from buffalo chicken waffle cones to homemade cracker jack beignets and more. The tour of architectural highlights lasts 2.5 hours and costs $60 for adults 13+, $80 for adults with alcohol 21+, and $35 for children 12 and under. You can purchase tickets at

When: Nov. 16-17 from 10 a.m. – 12:30 p.m.

Where: 3635 N Clark St, Chicago, IL 60613 

Art on the Mart

Witness a curated digital art installation at The Merchandise Mart’s river facade across 2.5 acres – the size of two football fields. It will be accompanied by performers, prominent composer’s work with sound, puppeteers and visual artists. The event is free.

When: Nov. 15 from 6:30–9 p.m.

Where: 222 W. Merchandise Mart Plaza #470, Chicago, Illinois 60654

NEWCITY Annual Tree Lighting Festival

Make memories with your loved ones by enjoying live entertainment, train rides, Elf workshops of face painting, balloon twisting and ornament decorating as well as chances to take pictures under a giant tree at NEWCITY’s entertainment complex. Also, get a chance to meet Prancer and Vixen, the REAL reindeer that will be present at the festival. 

Family Yoga Day at Yoggic Chicago

Pack your mat, grab your bag and put on your sports’ gear to head to an afternoon of yoga at Buddha Belly. This event is free with a suggested donation of $10, which will benefit the Africa Yoga Project. It will provide a scholarship for two African youth to travel to Nairobi, Kenya in April 2020 and receive yoga teacher training. From crawlers to seniors, everyone is welcome to attend and have fun with the entire family.

When: Sun, Nov. 17, 2 – 3:30 p.m.

Where: 3110 N. Sheffield Ave, Chicago, IL, 60657

Imagine the Moon

Visit the planetarium for a brand-new sky show that brings a new perspective on humanity’s relationship with the Earth’s longtime companion. You may purchase tickets at $35 for ages 12+, which include the museum entry and two sky shows of your choice. Children’s tickets between 3 to 11 years old are priced at $24 with the same access as the adult tickets.

When: Every day until Sept. 7, 2020 beginning at 9 a.m. – closed on Thanksgiving (Nov. 28) and Christmas day (Dec. 25).

Where: 1300 S. Lake Shore Drive, Chicago, IL 60605

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