The city of Chicago is known to flex its majesty during the Christmas season. Chicago comes alive with anticipation as temperatures drop and it is truly a magical place to spend Christmas with loved ones, new travel friends or even alone. From popular Christmas activities to lesser-known winter events, here’s your guide to things to do in Chicago at Christmas for all ages and budgets.
Christmas Things to do in Chicago
Table of Contents
1 The Bean Selfie
One of the most recognisable symbols in Chicago is that big silver bean at Millennium Park. Just because the ground is dusted/covered in the white stuff it does not stop winter lovers taking a reflection shot with the number one attraction in the city!
Officially called Cloud Gate, this stainless steel figure is the work of Indian-born British artist Sir Anish Kapoor and is made up of 169 polished plates, that’s a lot of cleaning! If you are doing it for the ‘Gram, you might want to get a picture of Lake Michigan completely frozen up with Chicago skyline standing behind.
If you like street art, don’t miss the new Wabash Lights at Chicago’s Loop. These LED lights underneath the Wabash el tracks are looking to grow so even if you’ve seen them you’ll need to go back to watch them expand.
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2. Sledding In Chicago
Sledding is a great way to bond with family and friends during cold winter days.
Every Christmas holiday, sledging enthusiasts head to Cricket Hill at Montrose Harbor, Palmisano Park in Bridgeport, the Dan Ryan Woods and Soldier Field. These hills offer the perfect sledding places and they are safe for kids too.
For people looking to sled away from the city, they can head out to the suburbs where places like James Park (Evanston’s “Mount Trashmore”) and Polar Peak at Frozemont (Rosemount MB Financial Park, 20 mins from Chicago Downtown) reign supreme.
3. Ice-Skating In Chicago
Just because it is Winter it does not mean that you cannot enjoy outdoor activities this Christmas. Chicago has a number of one-of-a-kind ice skating rinks all over the city.
There are both indoor and outdoor rinks where thousands of people visit during Christmas. One of the most visited rinks in Chicago is the Mccormick Tribune Ice Skating Rink at Millennium Park.
It is open from November to March every year. Look out for the 2-4-1 offers which let you skate both Millennium and Maggie Daley Park.
If you are new in town, you can hire ice-skating gear. One of the family-friendly things to do in Chicago in winter.
4. Have Glogg At Simon’s Tavern
New in the city and looking for the perfect night spot to spend quality time with friends? The Simon’s Tavern was recently voted as the most loved bar in all of Chicago.
The place is perfect for people looking to enjoy a night out during the Christmas period. You can cosy up with friends, knock back the tavern’s famous spiced wine and feed the jukebox all night long.
During the holidays, a special neon sign is put up on the front window proclaiming “Its glogg time!”
If you are looking to drink by an open fire, head to Broken Shaker or Drumbar for outside fire with the classy twist.
5. IO Godfrey Igloos
Climb inside the heated igloos of the Godfrey Hotel’s rooftop winter scene!
These dreamy see-through igloos keep you warm while you drink and enjoy the views.
6. Frosty’s A Christmas Bar
Head to 809 W Evergreen (Goose Island) for Frosty’s pop-up Christmas bar which has heaps of Instagrammable props like swings, giant soldiers and candy canes. Get ready to party at Frosty’s!
Polar Express Pulls Into Chicago
Hop aboard the CTA’s holiday train which is decked out in over 60,000 lights, tinsel and a visit from Santa!
Check out the official CTA website for stops this winter.
7. Wrigley Building Christmas Tree
Stunning tree at Wrigley Plaza which pops against the glazed terra-cotta on Magnificent Mile.
8. Christmas Shopping in Chicago
Looking for a special gift for a loved one? How about you head to one of the many holiday markets in Chicago.
As you browse the markets, you will experience the wintertime magic while having a blast shopping for the perfect gifts for everyone on your list.
The seasonal market circuit offers a variety of merchandise from Chicago-themed gifts to sugary confections to vintage clothing. You are free to enjoy a boozy beverage as you shop.
Christkindlmarket at Daley Plaza in downtown Chicago is where you will find the European inspired Christmas market stalls and lights to boot.
If like me, you prefer vintage shopping head to the Lower West Side for Knee Deep Vintage, Richard’s Fabulous Finds at Wicker Park (I love this area) and Encore Resale Clothing at Hyde Park.
9. Visit Chicago’s Toy Stores
Chicago has a number of toy stores. During the Christmas season, the shops are open until late hours to accommodate the number of last-minute shoppers.
The toys available at these stores aren’t just for kids. You will find all sorts of toys including rare collectables.
One of the places to visit in Chicago during winter is Macy’s (the old Marshall Fields) to see the 45-foot tree in the Walnut Room.
10. Check Out The Latest Christmas Films
Every year, there are Christmas themed films that get released in cinemas.
Chicago is home to one of the best cinemas equipped with the latest technology to provide a thrilling experience to movie buffs.
There are several films released each year with different ratings.
Instead of staying home and enjoying the same Christmas films you have watched over and over, why not head to one of the cinemas in Chicago and catch the latest Christmas film. Bring along the whole family to make the experience memorable.
Alternatively, what about Christmas date night?
AMC Dine-in Theatres Block 37 lets you eat a freshly prepared meal, have a drink in hand and watch a film!
Logan Theatre (2646 N Milwaukee Avenue) is an old-school cinema with crushed velvet seats and cheap show tickets. You can expect new films, throwbacks and late-night movies.
11. Christmas Shows in Chicago
Do you enjoy watching live plays? Every year, local theaters in Chicago present both old favourites and new plays on stage. Most of these events are booked early to avoid the last-minute rush.
Check out the listing in a theater near you and get a ticket well in advance to book early. Bring along friends and you can head out for a late-night dinner after enjoying a live show.
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12. Adler Planetarium
Not specifically a Christmas activity but a unique point of interest in Chicago for those who like all things space-related (like the other, Scot, Craig) – Alder Planetarium (1300 S Lake Shore Drive).
Many of the shows start at midnight for obvious reasons. You can expect educational shows, hands-on activities and expert exhibitions.
13. Christmas Tree Lighting Ceremony
You will not have properly experienced Christmas in Chicago unless you do the things listed in this post, especially the Christmas Tree Lighting Ceremony.
Every year, the city of Chicago erects an official 50-foot+ Christmas tree in the majestic Millennium Park. It won’t just be the tree that is glowing as Christmas-lovers capture the event on their phones. There might just be another bright surprise for you too.
14. Museum of Science & Industry
It is the tradition that the Museum of Science & Industry plays host to the Christmas around the World event each year from the second week in November until January.
Expect a floor to dome sized Christmas tree surrounding bother small (but in no means small) trees decorated by volunteers. Each tree represents the different ways that Christmas is celebrated around the world, hence the title.
Museum of Science & Industry can be found at 5700 S Lake Shore Drive.
15. Chicago Christmas Lights Festival
Chicago’s Magnificent Mile (Mag’s Mile) is home to many hotels, shops and restaurants but for one night in November, the street comes to life with music, light and a few Disney characters thrown into kick-start the festive feels.
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Getting Around Chicago
It’s really easy to navigate downtown Chicago, like Glasgow in Scotland it uses a grid system. Downtown is divided by Madison Street (North and South) and State Street splits up East and West.
There is an extensive transport system for those who prefer not to walk and/or want to squeeze more in. The Chicago Transit Authority (CTA) runs the train and bus system in the city.
You can pay with cash for single trips or invest in reloadable Ventra Transit Card or Unlimited Ride Pass for multi-use savings.
The ‘L’ train covers 144 rail stations and two of the links operate 24 hours a day. The Blue Line links the airport (O’Hare) to downtown and the Red Link hooks up the North and the South. Some of the buses are also run 24 hours a day. You need the exact change for buses.
You can plan your journey use the Chicago route planner.
Weather in Chicago
You can expect highs of 17 degrees and lows of 10 degrees in October in Chicago with spells of cloud, sun and rain. The temperature drops 10/4 in November and then 3/-3 in December.
Expect ice and snow from December. Wrap up, wear layers and invest in a good quality waterproof coat like this Mountain Equipment and waterproof snow boots or trek shoes like my favourite Salomon. Why not escape the cold? Here are the best places to spend winter in the Americas.
If you are new to the city, visiting Chicago in December is an exciting time full of festivals and markets. If you are a local, I hope you’ve discovered something new to try out this winter. Please do tell us your favourite Christmas activities in Chicago below!
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