The Ultimate Chicago Holiday Family Must Do List

Every holiday season, something new pops up in Chicago that I can’t believe I missed. Talk about major holiday FOMO. In order to alleviate this millennial crisis, I create a Holiday Must Do List for my fellow Chicago families. These are my tested and approved family events and worth every minute and penny in my humble opinion. So go forth and be merry!

Photos with Santa
Santa HQ at Fashion Outlets of Chicago

Description: Santa HQ is a multimedia interactive experience centered around Santa’s workshop in partnership with HGTV. Take an Elfie Selfie to star in your own video, use Elf-Ray vision (download app here) to see secret scenes, and find out how you fall on the Naughty or Nice O’Meter. My kids LOVED all of the incredible events leading up to meeting the big guy, and their photos are second to none. For those who don’t celebrate Christmas or aren’t Santa-believers, there are SO many stores to hit up. Get some holiday shopping done at their more than 130 designer outlets and grab lunch at the extensive food court.

Open 7 days a week through December 24th
Monday-Thursday: 11am-8pm
Friday-Saturday: 10am-9pm
Sunday: 10am-7pm
For special holiday hours, see site here.

Various photo packages available; no charge to visit the HQ.
Make a reservation at the Santa HQ Website to reserve your time (no waiting in a massive, hours-long line).

Insider Notes:

  • Shoppers who donate a new, unwrapped toy with a value of $5 or more through December 20th will receive up to 4 general admission tickets to the Brookfield Zoo valid through December 31st, 2017. 
  • Pet night is every Monday from November 27th through December 18th! Bring your cat or dog for photos with Santa from 6pm to 8pm. For each pet photo package purchased, $10 will be donated to the Friends of Chicago Animal Care and Control.
  • The Chicago Dogs, Chicago’s new baseball team which will play at Impact Field currently under construction in Rosemont, have a pop up shop at the Outlets. Grab team merchandise and chat with the staff about this exciting addition to the Chicago sports scene!

Gingerbread House Decorating
Four Seasons Hotel Chicago

Description: Want to create a lasting memory for the family with minimal effort and maximum enjoyment? Come join the Four Seasons pastry team for a Gingerbread House Decorating party! Your family will be provided with a pre-assembled house, frosting and all the decorations. Charlotte, my 3 year old, and I decorated ours a week ago and she talks about it every day. Grab a room at the Four Seasons that evening to enjoy all they have to offer- from amazing lights up and down the Magnificent Mile to making a splash in their indoor pool, this will be a holiday to remember. PS- they have a kids club room, babysitting services and teen spa services as well as an ice cream man that comes to your room!

December 2nd and 16th; 1pm to 5pm

$100 per family
Call 312-799-4900 to make reservations; if there is no answer, call the main line at 312-280-8800.

Insider Notes: Ask the pasty chef how to make icicles and tree branches! They have a special technique that is easy to master, even for the youngest decorator.

Holiday Lights Tour
Double Decker Co.

Description: Imagine being chauffeured around to the most popular holiday destinations in Chicago on a heated trolley with your entire family. The Holiday Lights Tour is my absolute favorite in Chicago- you start at the John Hancock building among the Magnificent Mile holiday decorations and head straight to Sprinkles for the cupcake you will ever consume. Next stop? Daley Plaza for a visit to the Christkindlmarket to shop and snack, viewing Macy’s windows along the way. Warm back up on the trolley as you head to the Lincoln Park Zoo to stroll through their incredible lights display and see animals at play. No fighting traffic, just relaxing with your family and basking in all that holiday cheer!

Tours are available at 5:30pm, 6pm, and 6:30pm on the following dates:
November 24th-26th
December 1st-3rd
December 8th-23rd

Adults: $29
Kids 5-15: $18

Insider Notes:

  • Bring warm clothes!! Although the trolley is heated, you will be jumping off for about 45 minutes or longer at both stops. You will be with the same trolley and driver the entire journey, this is not a hop on, hop off event. 
  • At the market, grab the hot chocolate for the kids and an activity Passport at the Grand Timber Haus. It is filled with activities, coloring pages and a contest (although you might want to come back to complete it- time is limited!). Sign your kid up for the free Kinder Club here.
  • Some booths are cash only but there are ATMs at the Grand Timber Haus and Festival Tent.
  • The Christmas tree makes a fabulous family photo!

Cheers to the holiday season, and hanging out with the family in stress-free situations!

Disclaimer: I was hosted for each of these events, but all opinions are honest and my own. Photos for the trolley courtesy of Chicago Double Decker Trolley Co.