Christmas in Chicago is a truly magical time–there’s so much to do for the holidays. Whether you’re looking for festive ideas while visiting from out of town or wanting to start some new traditions as a local, I’ve got you covered with these 15 ideas.
Kate Kennedy from Be There in Five Podcast has talked about the nostalgia of experiencing Christmas as a child and how it just doesn’t feel as special as an adult. She realized that much of the joy and wonder of the season was actually the result of adults putting in a lot of effort for their children– through decorations, baked goods, planned family events, gifts, food, movie nights, etc.
As we grow up and into our own lives, we have to make that magic ourselves which can feel a little lackluster. Maybe you’re too busy one year and skip putting up a tree and lights. Maybe you miss out on events you used to love because no one is planning them for you anymore. Or maybe you moved away from family and the holidays feel lonelier.
Childhood memories will always hold a special place, but we can create a magical holiday season as adults, too! I hope this list helps inspire you to plan something festive or start a new tradition you can look forward to each year.
1. The Music Box Theatre (my personal favorite Christmas in Chicago tradition)
This is something I did with family for years as a teen and always looked forward to. It got me in the Christmas spirit every time. Each year, the Music Box Theatre plays a double feature of It’s a Wonderful Life and White Christmas and has Santa come at intermission to sing carols. They’ve been doing this for something like 40 years! The theatre is gorgeous in its own right which makes this experience even more magical (the walls and ceilings are very cool but I don’t want to spoil the surprise of seeing it yourself). To this day I always watch these two movies for Christmas, but I need to bring back the tradition of going to see them at this historic theatre.
2. Lightscape at the Chicago Botanic Garden
This experience was new to me this past year, and I can see it becoming a holiday tradition for sure. I love art walks, so this was right up my alley. The Botanic Garden sets up various light displays by different artists (with music too) which you can meander through with mulled wine in hand! It was impressive and a fun way to spend a few hours.
3. Christmas-themed Bar Crawl
Chicago definitely participates in pop-up bar culture, and during November and December, there are so many Christmassy locations to check out. My friends did a bar crawl last year at venues exploding with holiday cheer. I mean check out the pics from Santa Baby (one of the pop ups they visited)! Another stop they enjoyed was Frosty’s. These bars go HARD with the decor!
4. Christmas in Chicago: See “The” Tree
Christmas in Chicago wouldn’t be complete without an official tree! You can head to Millennium Park to see it and snap some photos–there’s even a lighting ceremony you can catch, usually sometime in November.
5. Eat, shop, and be merry at the Christkindlmarket
Transport yourself to Germany by heading to Daley Plaza for the annual Christkindlmarket! Shop for gifts and ornaments, drink mulled wine, eat pretzels and soup, and warm up with holiday cheer. In 2023 the market opened on the same day the tree was lit, so it could be fun to combine these 2 activities in one evening before the huge crowds appear closer to Christmas.
6. Ride the train with Santa
My friend and I were in the city last winter and had one too many Ubers cancel on us while we were trying to get to dinner. We decided to take the train which somehow I had never done before. We were feeling stressed due to running way late for our reservation, but when our train pulled up, Santa was there with his reindeer and elves. It totally turned our night around and felt so magical!
I had no idea this was a thing but apparently there’s one train (and one bus) each year that’s led by Santa and his reindeer. And his elves hand out candy! Totally worth checking out if you’re using public transportation at all during your visit. You can see more about the history of this service and the schedule here.
7. Christmas in Chicago Igloo Experience
Booking an igloo is something I want to do every year but forget to plan in advance and then they’re always sold out 🙁 So think ahead with this one! But how festive would it be to have food and drinks in a freaking igloo? Seems like the perfect way to celebrate a Friendsmas! The LondonHouse winter igloos are at the top of my wish list, but this article has a bunch more options to check out.
8. Ride the Polar Express
I originally wanted to talk about going to see The Polar Express at the IMAX Theatre on Navy Pier. I know so many people love watching that movie every year, but then I saw the theatre had closed! (They’re replacing it with a Chicago Fly Over experience.) However, if you’re looking to get your Polar Express fix, you can book a ticket to ride it from Union Station instead! This looks like it would be so sweet with kids.
9. Go Iceskating (then watch the Blackhawks ice skate lol)
This is such a classic Christmas time activity and Chicago has a plethora of rinks to choose from. You’ve got the Maggie Daley skating ribbon, the McCormick Tribune Ice Rink near Cloud Gate (a.k.a. The Bean), Wrigley Field (which also does a Christkindlmarket), the Sky Rink at the Peninsula Hotel, Navy Pier, and Fifth Third Arena (home of the Blackhawks). You can make this even more of a Chicago day if you catch a Blackhawks game afterwards! I’m sure you’ll have so much appreciation for the pros after an hour of your own graceful skating (or wipe outs).
10. Christmas in Chicago: get a festive coffee
I love living somewhere with seasons and enjoying all the seasonal food and drink that comes with that! Support a local coffee shop before you start your Christmassy day and treat yourself to a festive drink. I was obsessed with peppermint mochas last year. You can even do this at home by buying a seasonal creamer for December–talk about sparking joy every day and having a unique taste to look forward to each year.
11. BrewLights at Lincoln Park Zoo
My friends and I did this a couple years back and had a great time. It’s a similar concept to Lightscape, except the light displays are put up by the event company/zoo instead of commissioned artists. The main focus is the brews. It’s adults only and you get your little cup to sample festive beers! We also had way too much fun riding the merry-go-round, and so did everyone else. It warmed my heart to see adults let loose in such a childish, pure way.
12. Christmas in Chicago Theatre Night
There are few things I love more than the theatre, so I’m not sure why I haven’t made seeing a show an official Christmas tradition yet! Chicago has a great Broadway scene, so definitely browse their website to see what’s on. I know people love going to see The Nutcracker every year, so check out the Joffrey Ballet schedule (I think another company put on a hip-hop version too). Last year, there was a Christmas-themed Cirque du Soleil that came to town that I wish I bought tickets for. You could also go see a Candlelight Concert (how cozy!)–the option are endless!
13. High Tea at the Peninsula Hotel
This is for my people looking to get fancy for an afternoon. Put on your Christmas finest and head to the Peninsula (decked out for the holidays in a way only luxury hotels can) to have the prettiest sandwiches, dessert, teas, and champagne in their impressive lobby. They also had live, festive music and a Santa photo op (perfect for kids). This is on the pricey side but we loved it! Sometimes treating yourself to something nice is just what you need to feel special and create some magic. They don’t have tea every day of the year, but when they update the dates you’ll be able to find the details here.
14. Snowshoeing at the Morton Arboretum
I haven’t been to the Morton Arboretum during the winter, so I can’t speak on these exact activities, but I was there in the fall. Our day amongst the foliage was one of my favorite days of the whole year, so I really don’t think you can go wrong planning a visit any time of year! This happens a little bit after Christmas in Chicago, but from January- March you can go snowshoeing, and I bet it would be sooo beautiful with all the trees. I think that would be such a unique way to get some exercise and fresh air (you can rent snowshoes or skis if there’s at least 4 inches of snow). They also put on a light show (closer to Christmas) which I’d love to check out!
15. Macy’s Holiday Windows and Nordstrom’s Habitant Bar
In recent years, online shopping has become so normal. It’s convenient but it’s not an experience. I think a Christmas shopping day would be such a fun tradition to start (and you can also check things off your to do list)! Start by admiring the Macy’s Holiday Windows (located just a couple blocks off the Magnificent Mile on State Street). There’s also a restaurant inside called The Walnut Room which apparently does a fun Christmas tree made of toys. Could be worth making a reservation– you definitely need a lot of energy for shopping!
Next, make your way over to Nordstrom on Michigan Ave., which has a bar inside the store in the middle of the men’s department! Grab a seat to warm up and order a glass of champagne or a festive cocktail, then go shopping a little tipsy. Treat yourself to something you normally wouldn’t with that liquid courage or pick out your matching Christmas pjs for the year. It would be a great time to find that perfect white elephant gift too!
Christmas in Chicago Final Thoughts
I hope you feel inspired to make one new plan for Christmas after reading this post! We’re now the adults that have to put effort in to make the season feel merry and bright, but hopefully these ideas will bring you the joy and wonder it’s so easy to feel in childhood. Whether or not you start a new tradition, you’ll make some special winter memories at the very least– a gift in itself 🙂 Happy holidays everyone!