Skip to content

Holiday Fun In Chicago

Chicago is such a great city with endless things to do in every season. There are almost too many things to do so it makes it hard to choose! I put together a list of some of my faves and new events to make your season bright (and fun!)

First, we will start with family outings.

Santa outings are always a must in December and there are some great Santas out there.

Macy’s Santaland on State Street. Not only is Macy’s (Marshall Fields, I still call it!) gorgeous inside with holiday decor and adorned windows, but Santaland really feels like you’re walking through Santa’s Elves’ workshop as you wait in line for your picture with Santa. Santaland is free and picture packages start at $17.99. You can also make reservations to dine with Santa, there are several dates to choose from and ticket prices are $25 and under.

900 North Shops Hands down one of the most real looking Santas out there. He makes me believe! Open now through December 24th.

Santa Suite at Swissotel Chicago. According to their website: Opening Dec. 7th, the Presidential Suite is transformed into a stunningly whimsical display, only suitable for a visit from Mr. Claus. This over-the-top space is decorated in the spirit and magic of the season, complete with fifteen Christmas trees, a table set for Santa and his special guests along with snacks and giveaways to spread good cheer. Tickets for Santa Days went on sale on October 1st. For more information or to buy tickets, click here. We are headed there this weekend!

 Image provided by Glitter and Bubbles + Hallie Duesenberg

Zoo Lights Presented by ComEd at Lincoln Park Zoo. A yearly family tradition for us, the zoo lights feature 100s upon 100s of twinkling light displays and adventures for the kids. They host family nights on Monday, December 16, 23 and 30. Kids eat free at the Park Place Cafe and they have unlimited free rides on the Lionel Train and the carousel. Admission is always free.

Winter Wonderfest at Navy Pier. This is another family favorite every year. I recommend getting there when they open as that is when lines are short and it’s way less crowded. Right around lunchtime through the evening it gets very busy. There are rides and bouncy houses for all ages. They also have an ice skating rink. The kids love it! You can usually find discounted tickets on Groupon, too.

A Christmas Carol at the Goodman Theatre. I’ve seen this twice and it really is a great recreation of the timeless classic. With or without the kids, I highly recommend!

The Polar Express. Tickets are now on sale and they sell out fast! This will be our first year going, but I hear it is a blast. It’s a one-hour train ride of fun, snacks and hot chocolate on your way to meet Santa. Tickets run $48-$70 for adults and $38-$62 depending on peak times.

The Nutcracker. An all-time favorite of mine. I can no longer force my husband to go with me as he’s had enough, however, my oldest son is now interested in going. Yay! Running now through December 29th.

Hotel Zachary Breakfast with Santa. Guests can start a new holiday tradition with Breakfast with Santa at Hotel Zachary. On Saturdays and Sundays beginning November 30 through December 22, families are invited to enjoy a special holiday-inspired breakfast buffet featuring assorted pastries and bread, yogurt parfaits, scrambled eggs, biscuits and gravy, white chocolate peppermint pancakes, an omelet station and more, while Jolly Old Saint Nick relaxes near the fireplace, waiting to visit with good boys and girls, and listen to their holiday wishes. Reservations are recommended in advance and will be available beginning November 1, 2019.

photo credit: Chicago Parent

Gallagher Way Holiday Movies. Bundle up for movie nights in the park at Gallagher Way. Holiday movies show every Thursday night in December. If you want to head to the park another day you’ll be met with a Christkindl Market and ice skating rink.

Now for some adult-only fun.

I’ve said it before and I’ll say it again – you haven’t lived until you’ve been to a Christmas pop-up bar!

Frosty’s. A must-see for some holiday fun, a Santa spotting, and some delish holiday-themed cocktails. You have to have tickets and on weekends they usually sell out – so plan ahead!

Santa Baby. Another pop-up Christmas bar in Wrigley. Santa Baby is a multi-room, multi-level, over-the-top Christmas experience. I’ll be there just for the spiked hot chocolate! Who’s coming with me? I mean look at those photos from their website! You need to buy tickets for Santa Baby, which can be purchased through their website.

Happy Holidays, Chicago!

About Me


Holly Rust

Chicago Boy Mom – Author – Side-Gigging CEO On The Go. Social Media Maven. Eternal optimist. Lover of travel, food, style & beauty. Follow my random thoughts, favorite things and life shenanigans here. Be sure to follow me on social, too! Links below.

Follow on Facebook

Follow on