Things to Do

What to do in Chicago this December

As the year comes to an end, revel in Chicago’s holiday-themed festivities.

The waiting game is almost over as we head into an overly decorated holiday period in Chicago, dominated with Christmas events. With an unlimited supply of drinks, food, and fun, we have planned a captivating list of activities to make sure your holidays are loaded with euphoria.

Take your pick from cocktail-making classes, Christmas fairs, and historic NBA fixtures, as we round up the year in style.

City of Chicago Christmas Tree

(Throughout December)

chicagodecemberevents City of Chicago Christmas Tree

City of Chicago Christmas Tree, Source: Website

Standing tall in Millennium Park with its sparkling gown and a crown star on the top, the City of Chicago Christmas Tree has been a symbol of fiesta for over a century. Gather with thousands of people at the location and start your December with a good omen.

In case you have a problem spotting the festive tree, head to Washington Street and Michigan Avenue to find the twinkling giant. 

Ticket price: free.

Location - 201 E Randolph St, Chicago, IL 60602.

Timings - 8 am onwards, every day.

View on maps.

Ice Skating in Millennium Park

(Throughout December)

chicagodecemberevents Ice Skating in Millenium Park

Ice skating at McCormick Tribune Ice Skating Rink, Source; Website

Another winter attraction in Millennium Park, McCormick Tribune Ice Skating Rink sits right next to the humongous Christmas tree we just mentioned. Despite free admissions being permitted to the ice skating rink, you will need to reserve a spot online and rent skates if you don't have a pair of your own.

There will be beginner and intermediate level training classes along with training for ice hockey for those who love winter sports. 

So, what are you waiting for? Lace up your skates and float around the rink for an unforgettable experience. There will be snacks and hot drinks for sale from Momentum Coffee. 

Rates for the rental skates start at $13 per person. 

Location - 1 N Michigan Ave, Chicago, IL 60602.

Timings - given with each booking.

View on maps.

Book your free spot here. 

The Office Experience

(Throughout December)

chicagodecemberevents The Office Experience

The Office Experience, Source: Instagram

Calling all The Office fans for a stroll through the Dunder Mifflin set, The Office Experience comes to life with recreating sets of the show in 17 rooms across two floors. Become a part of the much-loved show with props and merchandise for an enticing pop-up affair.

You can take home the ‘World’s Best Boss’ mug, Nard Dog printed apparel and other items from the shop after a closeup with The Office environment where the romance of Jim and Pam flourishes.

Ticket price: starts at $37.50 per person.

Location - 520 N Michigan Ave, Chicago, IL 60611.

Timings - allotted with the tickets.

View on maps.

Book your tickets here. 

Read Next: 10 award-winning wines to sip on this Thanksgiving

FEW Cocktail Class: A FEW Killer Old Fashioneds

(Until Thursday, December 9)

chicagodecemberevents FEW Cocktail Class: A FEW Killer Old Fashioneds

Cocktail making class at Time Out Market in Chicago, Source: Website

Learn a thing or two about cocktail making with Few Cocktail Class: A FEW Killer Old Fashioneds at the Time Out Market in Chicago. The one-hour session will educate and help you master the art of cocktail making with the guidance of a master mixologist.

You get a $25 voucher to spend at the Time Out Market along with some cocktail-making essentials such as a bar spoon, a strainer, an 18 oz crystal mixing glass, a jigger, and a few riffs on the classic Old Fashioned recipe to take back with you.

Ticket price: $100 per person.

Location - 916 W Fulton Market, Chicago, IL 60607.

Timings - 7 pm onwards.

View on maps.

Book your tickets here. 

Feel Your Soul Jazz Brunch

(Until Sunday, December 19)

chicagodecemberevents Feel Your Soul Jazz Brunch

Feel Your Soul Jazz Brunch, Source: Website

Make your Sundays sweeter with the Feel Your Soul Jazz Brunch at Time Out Market in Chicago. Choose from a handful of options at the market and grub on delectable treats like pizzas, French toasts, baos, bacon & egg croissants, and more.

The mimosa pitchers will help run off these tasty dishes, coming in their own flavors from the classic orange, peach, and strawberry elderflower. Each pitcher serves up to 10 glasses.

Ticket price: walk-in entry at the market.

Location - 916 W Fulton Market, Chicago, IL 60607.

Timings - 11 am onwards, every Sunday.

View on maps.

Christkindlmarket

(Until Friday, December 24)

chicagodecemberevents Christkindlmarket

Christkindlmarket in Chicago, Source: Facebook

How could we leave out a Christmas fair for our December events lineup? The Christkindlmarket is a German iteration of a festive fair with the mandatory glühwein and pretzels. 

Although the vendor list isn’t officially out yet, it is certain that you will find hand-wrapped gifts, hot drinks, and homemade food at the holiday market in Daley Plaza.

Tag along with your group of friends or arrive with the family to jubilate in the Christmas mood.

Location - 50 W Washington St, Chicago, IL 60602.

Timings - starts at 11 am onwards.

View on maps.

Chicago Bulls v/s LA Lakers

(Sunday, December 19)

chicagodecemberevents Chicago Bulls v/s LA Lakers

Chicago Bulls at United Center, Source: Facebook

Chicago Bulls have started off the 75th NBA season on a bright note. The free-agent signings of Demar Derozan, Alex Caruso, and Lonzo Ball have turned a languishing franchise into serious contenders. On the 19th of December, the Lakers will come to town, still figuring out their identity with the presence of stars like Carmelo Anthony and Russell Westbrook alongside Lebron and Antony Davis.

For the first time since the Michael Jordan and Magic Johnson glory days, a Chicago Bulls and Los Angeles Lakers contest has the chance to steal the show. Will the Bulls run rampant and continue their progress or will the Lakers play spoilsport in Jordan country?

Ticket price: starts at $164 per person.

Location - 1901 W Madison St, Chicago, IL 60612.

Timings - 2.30 pm onwards.

View on maps.

Book your tickets here. 

Santa Baby Christmas Bar

(Sunday, December 19 to Friday, December 31)

A bar decorated with all things Christmas from Christmas trees, reindeers, jingle bells, and a lot more, Santa Baby is a welcoming experience made to please even the grumpiest grinches.

You will be served everything over-sized from Christmas-themed cocktails (Jingle Juice & Mega Yule Mule), pretzels, waffles, and more.

This is the place where everything related to Christmas comes together in a quintessential manner.

Location - 3505 N Clark St, Chicago, IL 60657.

Timings - book a time slot.

View on maps.

Make a reservation.

New Year’s Eve Party at JW Marriott

(Friday, December 31)

chicagodecemberevents New Year’s Eve Party at JW Marriott

New Year’s Eve Party at JW Marriott, Source: Website

Become a part of the extravagant New Year’s Eve Party at JW Marriott to end your year on a high note and enter the new one with a bash. Indulge yourself in a buffet of delicacies from the hotel with an unlimited supply of cocktails, while some of Chicago’s best DJs liven up the mood.

Anticipated to be one of the most entertaining and enthralling New Year’s Eve parties in Chicago this year, you can expect to be welcomed with the highest quality services, lavish amenities, and delightful cuisines.

Ticket price - starts at $119 per person.

Location - 151 West Adams Street Chicago, IL 60603.

Timings - 9 pm to 2 am

View on maps.

Book your tickets here.

Header image - Santa Baby Bar, Source: Instagram

Popular on Chicago Drinks Guide

Next Events

South San Francisco Conference Center, 255 South Airport Boulevard, South San Francisco, CA 94080, United States.

Bartender Spirits Awards 2025

Register Now

Morgan MFG, 401 N Morgan St Suite #204A, Chicago IL 60642

USA Trade Tasting 2025

Register Now

South San Francisco Conference Center, 255 South Airport Boulevard, South San Francisco, CA 94080, United States

Sommeliers Choice Awards 2025

Register Now

Related Blogs