My 7 Favorite Christmas Activities in Chicago

Growing up, Christmas, like so many other kids, was my favorite holiday. I had a lag in holiday spirit during my early 20s, but last year I started to feel ready to celebrate with vigor again and I personally think Chicago is one of the best places to delight in Christmas cheer! I am biased, I did grow up here but that means I know all the cool things to do! So here are my recommendations if you’re looking to fill up your holiday calendar:

  1. Have a glass of wine at Marshall Field’s Great Tree.

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Sorry, Macy’s! We are never calling this the Macy’s State Street Great Tree. Marshall Field’s was a Chicago department store staple that went defunct in 2006 and was bought by Macy’s. Luckily, Macy’s kept the structure of the store alive since it’s such a landmark and continued the tradition of the Great Tree. Basically, it’s just a giant tree in the middle of a big restaurant but you can eat right underneath it and they have women dressed as fairy princesses wandering around granting wishes and most of the food is holiday themed.

PRO TIP: The food here has gotten worse and worse over the years and it’s really not worth coming for a full meal (especially now that it’s a buffet – so weird!), so I recommend skipping the long line to get a table and sit at the wine bar that is just to the right of the tree. You still have a great view and you can get a partial a la carte menu and just get the Frango Mint pie, a poinsettia (it’s sparkling wine and a splash of cranberry juice) and thank me later.

2. Shop local on the West Town Winterfest Jolly Trolley!

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I was invited to the Jolly Trolley last year and it was probably the most fun I had all holiday season. Here’s how it works: you pay $20 to have a seat on the Jolly Trolly that is packed full of booze and Christmas music and people ready to shop! It stops at 4 different locations around West Town and you have about an hour to shop at each stop. They give everyone a little map of the area too so you know which shops might have special discounts or are giving out mimosas or free cookies! It’s a way to shop local for the holidays and have a great day out with girlfriends or family. Some of the people I met on the trolley have been going to this for years!

3. Enjoy a holiday concert. 

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Last year, my sister and I went to see Hanson in concert for the holidays and they performed just their Christmas album. I didn’t expect to like it that much since it felt like it would just be a sing-a-long, but really it was so fun and the camaraderie in the room was infectious. So going to a pop-centered holiday concert is a new thing I love doing during the holidays. In fact, I’m going to see Brett Eldredge tonight! If you’re looking to still go this year, I hear Pentatonix is in town doing their newest album and so is the Trans Siberian Orchestra!

4. Bring your own schnapps to Zoo Lights. 

Zoo Lights is like a Chicago holiday requirement. Some years I’ve even gone twice! If you’re not from Chicago, the Lincoln Park Zoo lights up their zoo with a huge lights display and even some light shows displayed to music (Feliz Navidad! Mariah Carey!). One year, a friend and I went to Brew Lights – so fun! But it sells out fast. So last year, we decided to make our own fun and bring our own spiked hot chocolate to walk around the zoo with. It is almost all outside, so come prepared to be cold and definitely check out the ice sculpture display!

PRO TIP: Make a reservation for somewhere after if you are looking to have dinner. Places get bombarded by families and you will not be able to just walk in anywhere unless it’s a bar 🙂

5. Host a cookie exchange with friends!

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Not in the mood to make 3 kinds of cookies this year? Easy answer: have your friends help. We’ve been doing this tradition of having a cookie exchange for the past two years and it’s so fun! Each person brings about 15-20 cookies and everyone takes home 4 or 5 types of cookies. We also added a fun element of doing a champagne blind taste test competition last year. We each had to pick our favorite sparkling wine out of 5 on the table. I won because sparkling wine is my JAM.

6. Go on a Christmas Bar Crawl of Wrigleyville. 

It used to be that your one option to see an awesome Christmas bar in Chicago was limited to Butch McGuire’s. Not the case anymore! Chicago has 3 or 4 holiday pop-up bars opening up just for December and most of them are all within a few blocks of one another! Wrigleyville has the most and a few friends and I might just make a pilgrimage to try them all out next weekend! Here is a list from Eater of all the bars that are dressing up for the holidays.

7. Take a holiday crafting class. 

Last year I took TWO crafting classes during the holidays and I had so much fun. One was at Bottle & Bottega and we painted wood pallets with little holiday sayings like “Let it Snow!” This year, they are doing holiday tote bag painting too! I also took a class with my favorite crafting queen of all time Jocelyn. Her company, J.Villa Workshop, does fun classes like making your own holiday needlepoint or your own decorations for wrapping presents. She is so calm and does a great job of teaching each and every one of her students. I’ve taken 3 of her classes and I am not a very good crafter myself so take that as a testament! She’s not offering any holiday classes this season (she just had a baby!), but she does offer private classes if you’re into that sort of thing.

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