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9 Fun Things to Do This Holiday Season

holiday outfit

Structured Knitwork Dress | Newbury Boots, also in brown | similar Coupe Glasses | Lip Sheer in Currant

The holidays always go by so fast and when they’re over I make promises to myself that next year I’ll do all those things I wanted to this year. Anyone else? When Thanksgiving hits, I feel like I have so much time until Christmas and I keep pushing things off until all of the sudden I look up and it’s December 21st and we’re leaving the next morning to visit family. In a blink of an eye, December is nearly over!

It’s a tough time of the year though. Between holiday parties and travel, everyone gets so busy and it can make planning activities even harder! The trick to making fun activities happen is planning in advance, which to be honest, is not my strong suit. I think I have commitment issues when it comes to weekend plans, haha! But, as life gets busier and more complicated, I’ve learned that making plans in advance to do specific things is one of the best ways to keep up with our friends.

There are so many fun and festive things to do this season—both at home (because we’re not going too far) and around your city so I rounded up some of my favorite winter activities, as well as a few that I think sound really fun!

vintage champagne glasses and striped dress outfit

striped dress with booties

Fun Winter Activities

Host a Wine Night at Home

Personally, I’m loving this idea right now. Why? Well, it’s been tough to leave the house for too long, so having people over is easy! It’s also a much cheaper way to get your friends together. Have everyone bring their favorite wine, so you can taste different ones and pick up some simple apps like a few fancy cheeses, dried fruit, nuts and anything you can easily pop in the oven from the freezer aisle (Trader Joes’s has lots of good options). To make it more festive, get dressed up!

Striped Dresses


Simple Gift Exchange with Friends

A few years ago, I was in a supper club with thirteen girls. Sadly, almost everyone in the group has since moved from Chicago, but for Christmas we did a fun holiday dinner and simple gift exchange that was so much fun. We drew names, but kept it a secret, then set a price point and exchanged gifts at our dinner! It was such a fun night and the gifts made it extra special.

Holiday Tea

Last year, I went to holiday tea at The Drake Hotel with a few friends and it was so much fun. We got dressed in festive holiday attire and drank champagne, tea and ate fancy treats on a Sunday afternoon. up on a random Sunday went on a Sunday afternoon. For this one, you will need reservations in advance, and I recommend making them early as it books up fast!

fox ornament on christmas tree
polka dot grey christmas stockings

what to wear to a holiday party

@anthropologie holiday dress
popping bubbly-party ideas


The Lincoln Park Zoo is already free and during the holidays, ZooLights happens. I actually haven’t been, but I’ve heard it’s a really fun way to get outside during winter and look at some pretty lights. It’d be a great activity to do with kids too! Do a quick search to find out which fun and free activities your city has going on during the holidays and take advantage. Christkindlmarket is another one of Chicago’s holiday activities I love!

Walking Lights Tour

Looking at Christmas lights makes me feel so nostalgic for my childhood and totally gets me in the Christmas spirit. Scope out the best neighborhood for light viewing and whip up a hot cup of coffee or hot cocoa, heck spike it with some peppermint schnapps if you want—I won’t judge! Enjoy your own lights tour with friends or your partner for a fun, simple and romantic night out.

christmas tree decor

winter outfit for holiday party

winter outfit ideas
jcrew nordic boots

Adopt a Child or Family for the Holidays

I remember doing this back in school and loving it! There’s so much focus on buying gifts for your family and loved ones, but I always like to be able to find a way to give back to someone else. You can adopt a child or a whole family through different charities like Salvation Army or do a quick search to see what’s available in your city. Go in with friends or your family and spend an evening shopping for your adopted family. You’ll have so much fun shopping for someone else and feel good about being able to make someone else’s holiday extra special.

Black Booties


Draw Names

The holidays get expensive! Instead of buying everyone in your family a gift, draw names. Now that we have several brothers and sister-in-law, we’re doing this with both of our families. It makes the holidays more enjoyable because we get to focus on spending time with each other, not shopping or worrying about our budgets.

holiday party ideas

striped backless dress
holiday party outfit

Host a Cookie Decorating Party

Sprinkles, icing and cookie dough are cheap and it’s a fun way to get friends together! Serve light apps and drinks to turn it into a party, or make it family-friendly and set up a kids table too. The best part? The cookies mean that you have a built in party favor for everyone!


Go Ice Skating

Chicago has a beautiful outdoor skating rink in Millennium Park, and while I may not be good at ice skating, it sounds so much fun! It’s right off Michigan Avenue which is decked out for the holidays and would be a great way to get into the holiday spirit!

christmas party outfit

Which of these sounds most fun to you? Do you have any holiday activities you make a priority every year? What other holiday activities should I add to my list?

BTW, peppermint avocado brownies, and holiday tea at The Drake.