This Guide has been generously sponsored by Music Theater Works
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For more than a century, audiences around the world have been inspired by the story of ANNIE, the spunky, red-headed orphan whose unshakable optimism transforms everyone she meets, including billionaire Oliver “Daddy” Warbucks. Winner of seven Tony Awards, including Best Musical, ANNIE shines with some of the most beloved songs in musical theatre history, such as “Tomorrow,” “NYC,” and “You’re Never Fully Dressed Without a Smile.”
Tickets are now on sale for Music Theater Works’ ANNIE with guests 25 years old and younger available at half-price - perfect for the whole family. Playing for a limited time, December 19 - January 4 at the North Shore Center for the Performing Arts in Skokie.
Tickets and more information at MusicTheaterWorks.com
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.
HOLIDAY DINING
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 29th - December 21st at 7am-10am
Cost: Adults $60/Children 4 to 12 years $25
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, December 6th - December 28th at 1:30pm, 1:45pm and 2pm
Cost: Adults $75/Children 4 to 12 years $50
HOLIDAY LIGHTS AND MORE
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.
(There is an Illumination sensory evening on Tuesday, November 18th, from 4:30 to 9:30 p.m.; last entry is at 8:00 p.m. This modified experience will feature static lights and music at low volume.)
When: November 15th - January 3rd
Cost: $16+ for members, $20+ for non-members
CHICAGO’S ONLY DRIVE-THRU CHRISTMAS LIGHT SHOW.
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 4th, 5pm-9pm
Cost: $29.99+
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. New this year, Jingle Jam Family Nights - December 16, 17, and 18, kids can meet Santa and Mrs. Claus, the Snow Queen and other friends along our illuminated trail and get a free glow stick! Family Nights also feature fun food like pizza wreaths, s’mores kits, and hot chocolate for purchase, and family-friendly music at our dazzling Dance Party.
When: November 14th - January 4th
Cost: Adults $26+/Children 3-12 $14+
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 7:15pm.
When: November 22nd at 5:30pm
Cost: Free
7. Tree Lighting Ceremony at Gallagher Way
Join your friends, family and neighbors for an evening of holiday cheer with special performances, giveaways and more festive fun. Cradles to Crayons will be on site accepting donations for the holiday season. Afterwards, stick around Winterland to enjoy the festivities. Stroll around Christkindlmarket, ride the Holiday Train, visit with Santa and more.
When: December 5th at 6:00pm
Cost: Free
Wrigleyville Wonderland is back! The baseball-centric neighborhood transforms into the North Pole with over 15 Holiday themed bars. These pop-ups did much more than deck the halls, they’ve decorated every square inch of their spaces to bring holiday joy to even the grouchiest of grinches.
When: Various dates per location from late November to early January
Cost: Free
9. ZooLights
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 11th.
When: November 21st - January 4th from 4:30pm-9/10pm.
Cost: $7-$12 (Mondays excluding December 22nd are free)
10.Santa's Village Magical Christmas Drive-thru
Drive thru millions of lights, visit Santa, and glide down a snowless tube slide.
When: Select Dates November 28th - December 30th from 5pm-9pm.
Cost: $29.99/vehicle
HOLIDAY SHOPPING EVENTS
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 7th 1pm-5pm
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 29th
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 5th from 5pm-9pm
Cost: Free (Cocktail Crawl $33+)
14. Northcenter Holiday Trolley Days
When: December 13th & 14th from 12:30pm-4:30pm
Cost: Free
HOLIDAY SHOWS AND PERFORMANCES
15.It's a Wonderful Life 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.
When: December 12th - December 31st
Cost: $33 Students contact the Box Office at (312) 820-6250
16.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
MORE UNIQUE NUTCRACKER PERFORMANCES
17.The 42nd 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 6th - 24th
Cost: $17 Adult/$10 Child
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 5th, 12th, and 19th at 6pm
Cost: Free
19.More options to check out this year are:
Music Theater Works Presents Annie
Cirque du Soliel 'Twas the Night Before at The Chicago Theatre
Mrs. Claus! A Holiday Musical by the Chicago Kids Company
TRAINS
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.
When: November 28th - December 22nd
Cost: Standard CTA fare
A LITTLE OF EVERYTHING
21.Jack Frost Christmas Pop-Up
For one month only experience a larger than life, outdoor, multi-sensory, adventure in the heart of Chicago. Whether you're seeking a striking nighttime lights display, an outdoor Christmas-themed party with dozens of Holiday themed instagrammable memories or a full-sized ice rink, there's an experience here for everyone.
When: November 22nd - January 3rd
Cost: $18+
22.Winterland at Gallagher Way
This holiday season, stop by Winterland at Gallagher Way with friends and family. With music, Santa, seasonal food and drinks, and rides, you can expect plenty of free holiday cheer anytime you visit Gallagher Way!
When: November 23rd - December 31st
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.
