12 Fun, Festive Ways to Celebrate the Holidays in Chicago this December

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I don’t like to sit still, a symptom of neurospiciness. That has been an issue for me in the bitter cold of a Chicago winter. At the same time, I don’t want to be pressed up against strangers in a huge crowd or my anxiety will kick in. Below is a varied list of activities that have gotten me out of the house and into the wintertime/holiday spirit without being too overwhelming.

For a detailed itinerary, check out Christmas in Chicago 3 Day Sample Itinerary for a December Visit to the Windy City.

Wander around the Lincoln Park Zoo Lights Holiday Displays (Nov 15–Jan 5, $7-10)

For non-Chicagoans, this is a small zoo inside of Lincoln Park that puts up lots of lights in time for the holidays. Walk around admiring the holiday displays and sip on spiked hot chocolate or hot cider at the bar/restaurant. Unique opportunity to check out the animals at night when some of them are more active!

Be sure to get your tickets in advance to nail down a preferred day/time.

Note that there is typically a long line to get in even with tickets, but not to worry, the line moves really fast. This is such a great date night spot!

ChrisKindlmarket and Maggie Daley, Ice Skating ribbon (Nov 22 – Dec 24)

A very popular December destination in Chicago, the ChrisKindlmarket is a little sampling of what Christmas Markets in Europe are like: visit cute little stands to try pastries, buy some stocking stuffers, and even go ice skating! The Belgian hot cocoa is pricey, but very rich and delicious. Also a very cute date spot!  

Afterwards, check out some ice skating at Maggie Daley – I like this one because it isn’t an ice rink, it’s an ice ribbon curving around and up and down a bit. Lots of fun!

Note: this year there will not be a ChrisKindlmarket at Wrigley Field due to the NHL Classic.

NHL Classic is being held at Wrigley field on December 31st Tickets range from $280-$875.

This would be a pretty fun way to spend New Year’s Eve: bundle up to watch the Blues vs the Blackhawks play inside of Wrigley Field.

Chicago Museum of Science and Industry: Christmas Around the World exhibit (Nov 16-Jan 6)

See more than 50 trees and displays decorated to represent cultures around the globe. Advanced tickets are $25.95 + Museum Entry Fee

Not holiday themed, but just seems like a cool thing to do, for an additional $18, check out the 007 Science exhibit: iconic cars, gadgets and props of the James Bond film series.

Note: (prices noted are for non-residents, Chicago residents get a discount)

Dessert at the Chocolate Bar lobby of the Peninsula (Friday / Saturday nights – 7pm-11pm, $65/person)

The Peninsula Chicago is the five-star hotel in downtown Chicago well known for it’s top tier service. If staying here is out of the budget, you can still experience a little slice of luxury with their weekend Chocolate Bar hosted in the lobby of the hotel. Service includes gourmet hot chocolate and delicious desserts. Make sure to come hungry!

Macy’s Walnut Room for Breakfast or Lunch

A December favorite for locals, visit the Macy’s Walnut Room for a breakfast buffet or lunch service. Enjoy the festive decorations including the Great Tree, a holiday photo favorite. Reservations advised, though a small number of walk-ins are accepted each day.

For the kiddos, Breakfast with Santa is available:

  • Sunday, December 8, 8am-11am
  • Sunday, December 15, 8am-11am
  • Sunday, December 22, 8am-11am

Book an experience Starbucks Reserve Roastery and Enjoy a Seasonal Espresso Martini or Get a Front Row View at the Nov 23 Lights Festival Parade ($45-$150)

According to the site: Relax, have a Starbucks Reserve® Espresso Martini, and beat the crowds this year at the The Wintrust Magnificent Mile Lights Festival. ($150). Note: There is a $1200 ticket for VIP tickets, which is honestly crazy, but I’m not here to yuck anyone’s yum!

On all other days, there are experiences like Art of the Espresso Martini  behind the scenes tours offered ($45-$95).

Shop the boutique artistic shops in Andersonville

Travel to the Andersonville neighborhood of Chicago to visit the many cute independent shops in town including the Andersonville Galleria where 110 artists have displayed their wares. Be sure to eat at Hopleaf, a Belgian brewery and restaurant, one of my faves!

It’s a Wonderful Life play at American Blues Theater

It’s a play! It’s a radio broadcast! It’s both! Magical experience that is designed to get folks into the holiday spirit. American Blues Theater is a very small, intimate theater–very low key. A perfect holiday evening would include attending the play and then going out for a cocktail to a more low-key holiday pop up bars like the Pink Squirrel Tinsel Town (also a duck pin bowling venue!)

Alternative live performances:

Rent an Igloo with Friends

According to Secret Chicago, here are 10 additional igloo dining options. Just be sure to read the fine print, some require quite a hefty deposit: the Godfrey, for example requires a $250 non-refundable deposit that gets added as a credit to your bill.

Holiday Pop Up Bars

Are they tacky? Yes. Are they worth it? Most of the holiday ones I’ve attended, yes. Great opportunity to get together with friends, wear a tacky sweater, and take pictures with tacky over the top holiday décor! Here are some popular destinations:

Have a holiday-themed high tea at London House (Nov 16, 2024-Jan 12, 2025) $95/person

Perfect for a special occasion. This is one I would bring my dad too as a birthday gift, he has the unfortunate luck of being born on December 19th and ever since he was a kid, most people lump in his birthday and Christmas gifts together. As a sugar fiend and lover of all good food, I think he would love this experience.

Did I miss any must-try activities in Chicago? Comment below!