2023 Guide to Our Chicago Holiday Bucket List

20+ Flanagan Family Favorites!

By Debra Flanagan, Macaroni KID Chicago Northside November 14, 2023

This Guide is sponsored by Sparkle Light Festival
Discover the ultimate holiday destination with Sparkle Light Festival at Impact Field in Rosemont! Open November 17 through December 31, immerse yourself in millions of sparkling lights as you stroll through illuminated villages with custom holiday features. Visit Santa Claus, ice-skate with friends, enjoy free train rides on the “Holly Trolly” train, go tubing down the Alpine Slide, and more! Bundle up and indulge in festive food and drink as you experience the area’s premier outdoor light festival.
For tickets and more information visit!


I know, Halloween only just happened, but we are already getting our 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.


1. Breakfast with Santa at Hotel Zachary

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 near the fireplace, waiting to visit with good boys and girls and listen to their holiday wishes.
When:Saturdays and Sundays, November 25th - December 23rd at 7am-11am 
Cost: Adults $45/Children 4 to 12 years $20

2. Teddy Bear Tea at Hotel Zachary

Families are invited to enjoy a festive tea service, featuring Rare Tea Cellars. Children can indulge in a pot of house-made hot chocolate, tea sandwiches and light bites, scones, cupcakes and more sweet treats.
When:Saturdays and Sundays, November 25th - December 23rd at 1:30pm, 1:45pm and 2pm 
Cost: Adults $60/Children up to 12 years $30



3. Illumination at The Morton Arboretum

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.
When: November 18th - January 6th
Cost: $11-$22 for members, $16-$27 for non-members

4. Light of Christmas

Remain snug in vehicles and tune into a designated radio station, and be transported into a mesmerizing realm adorned with over a million synchronized lights! Hosted at Guaranteed Rate Field, Home of the Chicago White Sox, the spectacular show offers a leisurely drive, meandering through enchanting archways and luminous installations, a delightful experience that caters to all ages.
With just one ticket per vehicle, gather all your friends and family for a joyful journey through this radiant wonderland!
When: November 20th - January 3rd, 5pm-9pm
Cost: $24.99+

5. Lightscape at the Chicago Botanic Garden

Embrace the season’s beauty and make spirits bright at Lightscape, returning to transform new parts of the Garden—including Evening Island—into dazzling landscapes you’ve never seen before. From radiant first-time installations to beloved classics like the Winter Cathedral, this year’s reimagined trail takes the fifth annual holiday celebration to the next level.
When: November 10th - January 7th
Cost: Adults $30+/Children 3-12 $17+

6. Magnificent Mile Lights Festival's Tree-Lighting Parade

The season usually kicks off for us with the Magnificent Mile Lights Festival's Tree-Lighting Parade. 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 at 7pm
When: November 18th at 5:30pm
Cost: Free

7. Sparkle Light Festival at Impact Field, Rosemont

Discover the ultimate holiday destination with Sparkle Light Festival at Impact Field in Rosemont! Immerse yourself in millions of sparkling lights as you stroll through illuminated villages with custom holiday features. Visit Santa Claus, ice-skate with friends, enjoy free train rides on the “Holly Trolly” train, go tubing down the Alpine Slide, and more! Bundle up and indulge in festive food and drink as you experience the area’s premier outdoor light festival.
When: November 17th - December 31st
Cost: $24 Adults/$18 Children 2-12

8. Wintrust Tree Lighting Ceremony at Gallagher Way

The Wintrust Tree Lighting will be emceed by former Cubs pitcher Ryan Dempster, with a performance by Chicago Gay Men's Chorus and more festive fun. It will also kick-off the opening of Winterland at Gallagher Way.
When: November 21st at 5:00pm
Cost: Free

9. Wrigleyville Wonderland Friends and Family Night

It's the most wonderful time of the year! Join the East Lakeview Chamber of Commerce for a special night out on Clark Street and visit multiple holiday pop-up bars while they are kid friendly. Click here for more information on Wrigleyville Wonderland.
When: TBD
Cost: Free


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 a ferris wheel. There are Member-Only Nights, Sensory-Friendly Nights, and even an Adult-Only Night called Holidaze on December 14th.
When: November 17th - January 7th from 4:30pm-9/10pm.  
Cost: $7-$10 (Mondays are free)


11.Roscoe Village Winterfest: Sleigh Rides and Santa

Have a festive weekend starting with a tree lighting, shopping at one-of-a-kind boutiques, hot chocolate galore, and holiday cider. On Sunday afternoon, bring the family for children’s activities, caroling, and, of course, Santa!
When: December 1st - 3rd
Cost: Free

12.Small Business Saturday in Lincoln Square/Ravenswood

Not only do many businesses in the area offer special discounts and promotions, but festive events take place throughout the day. There are pictures with Santa, Victorian Carolers, and the annual Tree Lighting.
When: November 25th
Cost: Free

13.Southport Holiday Stroll and Cocktail Crawl

The Southport Holiday Stroll is a longstanding tradition in West Lakeview where businesses break out the holly and stay open late offering special holiday deals and festivities. The Southport Holiday Stroll is free to attend and includes special deals from local businesses, carol singers, photos with Santa, holiday treats, and other surprises! There is a ticketed cocktail crawl component that includes a commemorative tasting glass, event guide listing stops along the route, and tastings of 10+ different holiday-themed cocktails on your route while you enjoy the festivities of the Southport Holiday Stroll and shop for gifts at local stores!
When: December 1st
Cost: Free (Cocktail Crawl $25-$35)



14.A Celtic Christmas at The Athenaeum

Tomáseen Foley’s “A Celtic Christmas” brings the magic of the cold winter nights of his childhood to stages around the world. Modern day Chicago will fade away as the warmth of an Irish Christmas fills the theatre. The spirit of Christmas dances to life and glows brightly when the artists gather to create a wholesome, cultural, family feast from the rich table of communal life in the west of Ireland. Fiddle tunes, Christmas carols, and heartfelt storytelling—a holiday celebration you won’t want to miss.
When: November 29th at 7pm
Cost: $18+

15.Dance-Along Nutcracker at the Chicago Cultural Center

Though my kids have sadly outgrown the 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. The dancers are 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 have not yet been announced, but be on the lookout!
When: TBD
Cost: Free


16.The 40th Annual Music Box Christmas Sing-A-Long & Double Feature

Each year, holiday revelers are greeted by none other than Santa Claus, live and in person. Santa welcomes the audience and, accompanied by Music Box organist Dennis Scott, leads them in the singing of the most cherished Christmas carols of all time. The lyrics are projected onto the theater’s screen so no one misses a chance to sing their hearts out. Then the audience sits back and enjoys a Christmas movie classic or two.
When: December 8th - 24th
Cost: $14 Adult/$10 Child

17.It’s a Wonderful Life: A Live Radio Play at The Athenaeum

Inspired by the classic American film, It’s a Wonderful Life, “It’s a Wonderful Life: A Live Radio Play“ is performed as a 1940s live radio broadcast in front of a studio audience. Five actors perform the dozens of characters in the radio play.

Holiday Happy Hour: One hour before each performance will have happy hour specialty cocktails and live Jazz music to help you feel holly and jolly this Christmas Season!
When: December 15th - 20th
Cost: $20+

18.Millenium Park's Holiday Sing-Along 

One of my absolute favorite activities! 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.
When: December 1st, 8th, and 15th at 6:30pm
Cost: Free

19.Clue: A Walking Mystery - Holiday Edition

The iconic family-favorite board game comes to life this holiday season! Enter the world of Clue in the interactive and immersive experience, just in time for the holidays.Search for clues in downtown Chicago starting at Block 37 to solve the mystery in this interactive walking experience full of surprises with holiday spirit.
When: Friday-Sunday, November 17th - December 31st
Cost: $35

20.More options to check out this year are: 

The Beatrix Potter Holiday Tea Party at the Chicago Children's Theatre

Elf in Concert at The Rosemont Theater

Mrs. Claus! A Holiday Musical by the Chicago Kids Company

American Girl Live! in Concert (not holiday related - but playing one night only on Dec. 16th)


21.CTA Holiday Train 

If we are lucky, the CTA Holiday Train schedule will line up nicely with our commute to one of the other events on our bucket list. The schedule hasn't been announced yet, but they will indeed be running it this year.
When: TBD
Cost: Standard CTA fare


22.Wintrust Winterland at Gallagher Way

Whatever free time we have left will be spent at Winterland at Gallagher Way. From stealing away for a grab-n-go lunch from one of the Christkindlmarket Wrigleyville stands, (the reclettes are amazing), to watching a classic holiday film on the 40ft screen, to ice skating, there is always a reason to visit Winterland. New this year, a ferris wheel has been added to the train ride around the infield, tubing, and other rides and games. 
When: November 21st - January 7th
Cost: $5 entry to Winterland for ages 3 and up. Attraction tickets are extra. Admission to Christkindlmarket and Santa's Workshop are free.
Go to their website for special deals throughout the weeks.


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 add more events to our Events Calendar.