Chicago Christmas Bucket List

If you’ve been following me on social media you know that every December I embark on a major holiday kick. Christmas is my favorite holiday and Chicago is the greatest place to live during this festive time of year because everything from the decorations to the seasonal pop-ups are over the top.

From the annual Chicago tree lighting to ice-skating in Millennium Park, I’ve already participated in several Windy City Holiday activities; however, there are 13 days until Christmas and my bucket list isn’t quite yet complete. Here are a few of my plans with family and friends over the next two weeks.

1. ZooLights at Lincoln Park Zoo

The outdoor temperature may be frightful and many of the animals have headed indoors, but Lincoln Park Zoo has transformed into a delightful forest of twinkling bulbs. ZooLights runs until Sunday, Jan. 6, 2019, with a special Zoo Year’s Eve celebration taking place on December 31.

2. Christkindlmarket

My favorite holiday event in Chicago, the Christkindlmarket, runs through Monday, Dec. 24. The giant open-air market, inspired by a similar seasonal tradition in Nuremberg, Germany, features booths set up throughout Daley Plaza where you’ll find handcrafted German items like glass ornaments, cuckoo clocks, beer steins, and nutcrackers. As family and friends continue to visit the city, we’ve made several stops through Christkindlmarket’s Candy Castle to fill up on European chocolates, candies, and glazed nuts for our Christmas stockings. It’s also worth stopping buy to grab some potato pancakes, a sausage, or to sip a steaming mug of their traditional hot spiced wine.

3. Santa Baby Christmas Bar

Deuce’s & the Diamond Club got it right with their Christmas pop up bar. I’ve been to the establishment twice and both times were jaw-dropping experiences. From floor to ceiling, the entire building is decked out in twinkling bulbs, parachuting Santas, and flying reindeer. A mix of holiday tunes play throughout the bar and even the food takes a holiday twist as milkshakes appear as green as the Grinch with toasted marshmallows and Rice Krispie treats to top them off. If the holiday cheer wasn’t bursting at the seams already, Santa Baby Bar comes with a packed events calendar including Santa Claus appearances, Christmas movies playing every Monday, canvas painting on Tuesdays, Wednesday evening gingerbread house building contests, karaoke on Thursdays, and Sunday brunches. Deuce’s may be a bar, but the Christmas pop up is kid-friendly and admits those under 21 until 11PM. My teenage sisters and I have tickets for the morning of Christmas Eve and they can’t hardly wait. Check out more photos of Santa Baby Christmas Bar and get your tickets here.

4. CTA Holiday Train

A unique Chicago tradition, the Chicago Transit Authority decorates one of its trains, inside and out, with festive decorations and sparkling lights. Santa and his sleigh lead the train on an open-air flatcar, waving to boarding passengers as they pull into each station and riders are serenaded by elves between stops. Because of popular demand, the CTA Holiday Train now has a counterpart, The Elves’ Workshop Train. The Elves’ Workshop Train is six cars of festive magic, following behind the Holiday Train at every stop. Both trains operate on specific schedules to ensure the Christmas cheer is felt throughout all of Chicago. Find when both trains will be riding the rails nearest you here.

5. Holiday Movies at Wrigley Field

Every Friday through January 4, Wrigley Field’s Gallagher Way is showing free holiday movies on their video board. Each movie begins at 6PM and limited seating is available outside at Gallagher Way. You can watch while doing loops around the Gallagher Way ice rink or bundle up in the outdoor seating area. If the temperatures are too cold for you, select restaurants around Gallagher Way are showing the movies indoors. You can see the full list of Gallagher Way holiday movies here.

Photo By: Gallagher Way Chicago

6. Macy’s Holiday Window Exhibit

I’ve passed by these windows over 100 times, but I want to have one more time this season where I really stop and appreciate the artwork and craftsmanship behind the impressive window exhibit. Since the early 1870s, Macy’s has stunned spectators with its famous holiday window displays, and this year is no different. Thanks to the dedicated and talented team of painters, welders, costume-makers engineers, visual artists and carpenters, the Macy’s Holiday Window Exhibit on State Street is shining bright as figurines of Santa, Mrs. Claus, and the elves prepare for their busiest night of the year. The holiday window exhibit will be open until January 5.


  1. This is awesome, Brosh! We’re going to do our annual big Chicago Christmas lights & festivity stroll on Friday, and I had not heard of the Santa Baby Bar. Adding that stop to our route 🙂

    Thanks for sharing this – have an amazing holiday season!

    Liked by 1 person

    • It’s up in Wrigleyville! There is a $20.00 cover to get in on weekends, so if that doesn’t deter you – definitely check it out! Also, there’s no cover on Christmas Eve. That’s when I’m taking my sisters. 🙂 I hope you have a great stroll! Happy Holidays to you too!! If you need any other Christmas bar recommendations or restaurants with amazing lights (Homeslice Pizza has AMAZING decorations) then just let me know!


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