10 FUN & FESTIVE CHICAGO WINTER ACTIVITIES

SHOP THE POST
c/o J.Crew Wool Coat // OTK Boots {comes in 4 colors} // Leopard Tote
Black Leggings // Winter Hat // Striped Turtleneck // Sunglasses

Winter can be a cold one, but it’s also the most joyful time of the season. There are so many fun and festive things to do around this time of year in Chicago, so I thought I would compile them into a cohesive list for you:

1. CHRISTKINDLEMARKET AT DALEY PLAZA

This is always a fun activity to do during this time of year. There are so many cute little kiosks filled with holiday decor and delicious food. It is open from November 16th to December 24th and is totally free. You can bring your kids during the daytime, go during a lunch break if you work downtown, or head there at night for a festive evening out with friends!

2. ZOOLIGHTS AT THE LINCOLN PARK ZOO

This is always a great holiday tradition and not just for kids. Before I even had Elle, I would love to head down to the The Lincoln Park Zoo at night to check out the ZooLights. They have boozy holiday beverages and all the colors are so pretty. It’s best to go on a warmer night because it’s obviously all outside and also totally free to attend.

3. ICE SKATING AT MILLENIUM PARK

I’ve always wanted to do this, but haven’t had the chance yet. I probably haven’t even ice skated since I was in high school so hopefully I’ll remember 😉 . It goes until March 10th and skating is totally free and open to the public. If you need to rent some the cost is $13-$15 a pair depending on the day. I think this would be a great activity for older kids or even a cute date night.

4. THE NUTCRACKER AT THE JOFFREY BALLET

The Nutcracker is a classic and should be in everyone’s holiday tradition. I saw it a long time ago, but got to go again this year and it was absolutely FANTASTIC. The set design was out of this world and the dancing was simply beautiful. Once my daughter gets a bit older {she is only two}, I want to make this a yearly tradition. There are still lots of tickets available so make sure to get some before they’re gone!

5. THE POLAR EXPRESS TRAIN RIDE AT UNION STATION

I’ve been DYING to try this. I think it’s the cutest idea and so festive. If you love the book then this is the perfect experience for you! The one hour ride serves hot cocoa, cookies, and onboard entertainment. I think once Elle is a little bit older we will take her. You have to buy tickets so check the schedule and book today!

6. WINTER WONDERFEST AT NAVY PIER

I’m super excited to be attending this year. I love the fact that it’s inside {because Chicago is so cold!} and fun for all ages. They have rides, giant slides, indoor skating, and festive holiday decor. It runs until January 6th and you can buy tickets here.

7. DINNER AT THE WALNUT ROOM AT MACY’S

My husband’s family LOVES having dinner here every year. Macy’s does a great job of decorating for the holidays. It’s good to go early, because it can get really crowded, but the wait isn’t too bad. They also give out free holiday mugs and it’s always fun to check out all the window displays on your way in and out.

8. ‘TWAS THE NIGHT BEFORE CHRISTMAS PLAY

We’ve taken our daughter to this play the past two years. It’s super cute for kids of all ages and a great holiday activity. There is singing, dancing, and obviously an appearance of Santa. Make sure to get tickets in advance.

9. SKY RINK AT THE PENINSULA HOTEL

If you remember this post, then you know I’m a huge fan of the holiday setup at The Peninsula Chicago. They create the cutest little ice skating rink along with festive decorations, hot cocoa, and holiday cookies. Also champagne! We can’t forget about that 😉 . It’s fun to go with a group on a warmer day since it’s all outside.

10. THE SANTA SUITE AT SWISSHOTEL

Starting December 1st you will be able to visit the Santa Suite every Saturday and Sunday. There will be a letter-writing station, face painting, kids crafts, holiday decor, and most importantly a visit with Santa himself. There will also be a hot chocolate bar, holiday cookies and candy. I’ll actually be previewing the suite later this week with my family so make sure to follow me on Instagram Stories to get a sneak peek. To find out more details and for reservations and tickets click here.

While attending all these fun winter events, you will also need to have on a cute coat {because a lot of them are outside!}. Not only am I sharing some fun activities, but also details on my outfit below:

J.CREW WOOL COAT

I’m starting with this cute wool coat from J.Crew. I love the wool material of this one and it actually comes in a bunch of different colors. It was actually gifted to me by the company and want to share how you can help families in need this holiday season.

While your shopping for a new coat at J.Crew this season {and they’ve got a ton of cute ones!!}, consider donating a coat to their in-store drives in support of One Warm Coat between now and December 25th. You will receive $25 OFF your purchase of $125 or more.

OVER THE KNEE BOOTS

Everyone needs at least one pair of black OTK boots. These are extremely comfortable and look just like the Stuart Weitzman ones {but a fraction of the cost}. They’re easy to walk in and look great with dresses, long tunic sweaters, and even jeans.

SMALL LEOPARD TOTE

This tote has been a favorite of mine recently and I’ve been styling it a lot on the blog {as seen in this post and this pos}. It’s the perfect size, making it easy to wear both day and night. It keeps going in and out of stock, so snag it before it’s gone 😉 .

LEGGINGS

You can honestly never have too many pairs of leggings. I live in them during the fall and winter months. One of my favorite goto brands is SPANX. They make a wide range of styles and hold up great!

STRIPED TURTLENECK

I love stripes and this turtleneck is a great layering piece. It’s also currently on sale and comes in a few different colors to choose from. You can never go wrong with an amazing basic.

These photos were actually taken at The Waldorf Astoria Chicago. We got to attend their Christmas tree lighting ceremony. They have other festive holiday events going on throughout the month of December and the best decorations. Happy holidays guys!! xo