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Samantha Maloney

Festive things to do in Chicago this December

Updated: Dec 21, 2023

Holidays in Chicago are unparalleled...okay, maybe I'm a little biased but all the festive things the city has to offer are incredible. These are just SOME of my favorite things to do in Chicago this December!

1. Winterland at Gallagher Way - Nov 17 - Jan 7

Visit the friendly confines for some family-friendly fun! Winterland at Gallagher Way is an annual winter event held in Wrigleyville, Chicago. Gallagher Way is the outdoor plaza adjacent to Wrigley Field, home of the Chicago Cubs. Winterland transforms this space into a festive winter wonderland during the holiday season. Features of Winterland at Gallagher Way may include Ice Skating Rink, Holiday Market festive decorations, Live performances, music, and other entertainment, food and drinks, and other family-friendly activities!


2. Crawl to Christkindlemarkt - Select days Now until dec 30th

This laid back, create-your-own-adventure bar crawl experience helps you embrace the holiday spirit while casually strolling from bar to bar with your friends! Wrigleyville is home to some of the best bars in Chicago and most of these bars transform into festive popup bars during the holiday season. The bars are completely decked out in holiday flair and offer awesome photo opportunities for Instagram! Your VIP Pass includes admission to all holiday pop-up bars on the crawl, a specialty shot at each pop-up bar, souvenir postcard, giveaways and more! (purchase of a beverage required for specialty shot) Since this is a create your own bar crawl you can go to Wrigleyville's Best Holiday Pop-Up Bars in any order you choose All of the venues are within walking distance and lead you to Christkindlmarket in wrigleyville. Check out all the holiday pop-up bars and the shots they're offering below! Use code WINDYCITYSAM for 10% off your ticket!

Venues and shots offered are subject to change.


  • Elf'd Up (Stretch) - Candy Cane Forest Shot

  • Santa Baby (Bamboo Club) - Reindeer Games

  • How the Grinch Stole Christmas (Moe's Cantina) - Grinch Tea Shot

  • Santa's Workshop (Old Crow Smokehouse) - Gingerbread Shot

  • Ugly Sweater Bar (Nola) - Tipsy Reindeer Shot

  • The Nutcracker (Merkle's) - Espresso Martini Shot w/ Coffee Bean

  • Rizzo's Candy Cane Lane (Rizzo's Bar & Inn) - "Nice Shot!"

  • Almost Home Alone (Almost Home Tavern) - The Filthy Animal Shot


3. Christkindle Mart (Daley Center Plaza) - Now Until Dec 24

This one is one of my favorites! I made a whole post on instagram with some tips and tricks when visiting so be sure to check that out. Christkindle Markt Chicago is a timeless tradtion that sweeps you away to a small village in Germany for the holidays. Enjoy authentic German gluehwein, beer, and cider along with the BEST potato pancakes and sugar roasted nuts!


mug of mulled wine at Christkindlmarket chicago


4. The nutcracker ballet (Civic Opera House) - Dec 2 - 27

The Joffrey Ballet in Chicago is known for its gorgeous production of "The Nutcracker," a classic holiday ballet. In dazzling costume with wonderful choreography, the dancers are accompanied by a live orchestra portraying your favorite characters like Clara, the Nutcracker Prince, the Sugar Plum Fairy, and many others. Perfect for a festive night out!


5. Christmas around the world at MSI - Nov 18 - Jan 7

Explore a long-standing Christmas event, rich holiday traditions from around the globe while creating your own traditions! It began in 1942 with a single tree. Today, the Museum’s beloved annual celebration features a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 50 trees and displays decorated by volunteers to represent the holiday traditions from cultures around the globe. The display istelf is free with admission which is $26 for adults and $15 for kids. MSI is one of my favorite museums for kids since it's so immersive and the kids don't even know theyre learning!


enormous christmas tree at Christmas around the world Museum of science and industry MSI

P.S. Look how MASSIVE this tree is!


6. Jack frost Christmas pop up

The newest interactive Pop-Up Experience to come to Fulton Market! Experience this glimmering outdoor adventure in the heart of Chicago. Enjoy a beautiful nighttime lights display, an outdoor Christmas-themed party with dozens of Holiday themed instagramable memories, a full-sized Ice Rink, and axe throwing!


7. Brunch in the Walnut Room 

A classic holidays-in-Chicago staple! Dine at the Walnut Room located inside Macy's on State street. A decorated holiday tree stands 45 feet tall in the center of the room. Enjoy a holiday breakast buffet is offered on select day in November and December. It costs $30 for adults and $20 for kids. Bottomless mimosas are also available for an additional $25.


christmas tree in the walnut room Macys State Street Chicago


8. Pink Wonderland pop up bar 

Bask in all the Barbie-core vibes at this holiday pop up bar! Located in River North at 324 W Chicago, this adorable bar serves festive drinks and instagram worthy photo ops. Tickets vary depending on the date and time you visit but sundays are family days so the tickets are a little cheaper and kiddos can enjoy the Barbie life too! They also offer a cool cocktail workshop on Tuesday mornings where they teach you how to make their signature cocktails.


Festive drinks at Pink Wonderland pop up Christmas bar Chicago

I hope this helps get you in the holiday spirit! Let me know in the comments what your fave festive tradition is!


Until next time,

xoxo

Sam




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