I know, Halloween only just happened, but I am already getting my holiday plans together. For my family, the holidays aren't necessarily about gifting, or visiting with distant family. For us, it is predominantly about all the seasonal experiences in and around Chicago. We have quite a few annual traditions that include, in our opinion, all the best things to do.
- The season usually kicks off for us with the Magnificent Mile Lights Festival's Tree-Lighting Parade. The parade will take place on Saturday, November 20th at 5:30pm. We tend to watch at the beginning of the parade at Oak and Michigan, but if you go towards the end of the parade route, you'll be in great position to see the fireworks finale over the river.
- If we are lucky, the CTA Holiday Train schedule will line up nicely and we'll check that off our bucket list too. The schedule hasn't been announced yet, but they ran it last year, so I think it is safe to assume it will return this year as well.
- We go to the Tree Lighting Ceremony at Gallagher Way, which includes guest speakers, musical performances, and treats, followed by ice skating with Clark the Cub. This year, it will take place on Monday, November 29 from 6pm-9pm, and is free.
- December then begins with two of my absolute favorite activities - Millenium Park's Holiday Sing-Along (previously called Caroling at Cloud Gate) and the Dance-Along Nutcracker at the Chicago Cultural Center.
- Every Friday, beginning November 26th through December 17th from 6pm-7pm, and Sunday, December 12th from 4pm-5pm, hundreds of holiday revelers gather around Cloud Gate for a stunning view of the city in its reflection, and to join local Chicago choirs in festive songs. Each week is a different performance group, and free song books are distributed. We like to go early and get some skating in the McCormick Tribune Ice Rink just below.
- Though my kids have sadly outgrown the free, Dance-Along Nutcracker, it is any budding ballerina's dream come true, with the opportunity to participate in a short workshop with Ballet Chicago, and then watch them perform an abbreviated version of the classic ballet at eye level, accompanied by the Lakeside Pride Symphonic Band, under the gorgeous rotunda. The tiny dancers are frequently invited on stage to twirl, leap, and sachet, alongside the professionals. Soon enough, maybe my daughter will be one of the professionals and I'll get to go back! This year's dates, (if they are able to have it), have not yet been announced, but be on the lookout!
5. We go to three unique light displays. Six Flags' Holiday in the Park, Morton Arboretum's Illumination, and the Lincoln Park Zoo's Zoo Lights.
- Holiday in the Park at Six Flags Great America is running from November 26 - December 30, 2021. You can ride all your favorite rides, (no thrill rides this year though), while enjoying all the immersive light displays, holiday shows, and s'more-making fire pits. Dress warm, but don't leave without having a peppermint funnel cake sundae.
- Illumination at The Morton Arboretum isn't your typical holiday lights display. Journey along a one-mile, paved walking path amid festive music and lighting effects that highlight the beauty of trees in winter. It's an interactive experience with exhibits that can be controlled by a guest's voice, touch, or even a hug. Along the route, warm up by a crackling fire and roast marshmallows for s’mores, or stop in one of the concession tents for a hot beverage/cocktail.
- ZooLights is running from November 19 - January 2, 2022 from 4pm-10pm. Visit the animal exhibits at night while admiring millions of twinkly lights and large-than-life holiday decorations. There are also ticketed experiences such as a light maze and an enchanted forest. Admission is $5 this year, however Mondays and Tuesdays are still free. There are Member-Only Nights, Sensory-Friendly Nights, and even an Adult-Only Night called Holidaze on December 16th.
6. We will hit at least one neighborhood stroll among several including:
- November 27, 2021 Small Business Saturday in Lincoln Square/Ravenswood
- December 3, 2021 Southport Holiday Stroll & Cocktail Crawl
- December 5, 2021 Roscoe Village Winterfest: Sleigh Rides and Santa
7. We will have breakfast with Santa at Hotel Zachary. On Saturdays and Sundays beginning November 27 through December 19 from 8am-11am, families are invited to enjoy a special holiday-inspired breakfast buffet, featuring an assortment of upscale options for both children and adults to enjoy, while Jolly Old Saint Nick relaxes on his big comfy chair, waiting to visit with good boys and girls and listen to their holiday wishes. The holiday buffet is $50 for adults and children ages four to 12 are $20; pricing also includes choice of hot chocolate, coffee, tea or juice, and a visit with Santa. Reservations are required in advance.
8. Lastly, we attend at least one holiday show at the theater. This year the Elf on the Shelf: A Christmas Musical at Rosemont Theater on December 19th is calling us. Join us by purchasing your discounted tickets HERE.
Or you may prefer, ‘Twas the Night Before… by Cirque du Soleil. Appearing November 26 – December 5 at The Chicago Theatre. Use code MACARONI now through 11/19 to received 30% off select seats and performances.
9. Whatever free time we have left will be spent at the Gallagher Way Winterland. From stealing away for a grab-n-go lunch from one of the Christkindlmarket stands, (the reclettes are amazing), to watching a classic holiday film on the 40ft screen while ice skating, there is always a reason to visit Winterland.
- The Christkindlmarket Wrigleyville at Gallagher Way opens Friday, November 19, and gives visitors the opportunity to shop for the holidays and taste traditional German and international foods while enjoying family-friendly entertainment through Tuesday, December 31.
- Gallagher Way invites visitors to The Rink at Gallagher Way November 19 through February 20, 2022, weather permitting. The Rink welcomes all skill levels to skate on their own, participate in skating lessons, learn to curl and ride ice bumper cars, a new attraction this year.
- Lakeview’s historic Music Box Theatre will host classic holiday movies at Gallagher Way every Thursday in December, starting at 6 p.m.
- December 2: National Lampoon’s Christmas Vacation
- December 9: Home Alone
- December 16: Elf
- December 23: A Christmas Story
It's quite the list, isn't it? And of course, that's just a subset of all the great events, celebrating all the various winter holidays, in and around Chicago. Stay tuned as we continue to develop and publish our 2021 Holiday Guide.
