Our Holiday Traditions + Family Gift Exchanges

Over the years, a lot of you have inquired about our holiday traditions. How do we celebrate with our families? Do we have any traditions of our own? Do we have any good family gift exchange ideas we can share? All of these questions are wonderful and we’re here to finally answer them.

So let’s first break it down by how we celebrate the actual holiday (& the weeks leading up to it), then we’ll each share our family gift exchange ideas!

Casey’s Christmas TraditionsO'Halloran family Christmas card

Cookie DayCookie day quote

I’ve written about cookie day here on the blog before (check out this suuuuper old post) and I’ve even shared a few recipes (including these peppermint squares and these peanut butter cookies). Here’s how this annual tradition began…

When we were kids, we would spend one Saturday before Christmas baking cookies with my mom (& sometimes my grandma too if she was in town). We’d typically invite 1 friend over each and we’d spend all day baking dozens of cookies. At the end of the day, we’d drop plates off at our neighbors and friends’ homes. Making Christmas sugar cookies

As we got older, it turned into a much larger event. My siblings and I would each invite lots of friends and soon cookie day turned into a big party. We start the day with lunch, bake cookies all day long, enjoy some seasonal cocktails, and then order pizza when the last cookie is decorated. O'Halloran family cookie day partyMy mom has always hosted cookie day, but we actually moved the event to my brother’s amazing condo last year. In fact, last year we had 52 people come. It was insanity!

Cookie day is coming up on December 8th, so be sure to watch Insta Stories for all of the behind-the-scenes action!

Zoo Lights

My dad has started a Christmas tradition of his own. He’s a member of Brookfield Zoo here in Chicago and every holiday season they have “Zoo Lights.” They decorate the entire zoo in magical lights and you visit when the sun goes down and see all the animals. The light display is amazing and it’s fun to get hot chocolate and roam the zoo. My dad organizes it every year and we then head to an Irish pub for dinner and to warm up!

Elf on the ShelfElf on the shelf ideas

This one may seem a little strange, but Finn and I have started a tradition of our own. Even though we don’t have any kids, we certainly act like big kids ourselves. When we first moved in together, we started an Elf on the Shelf game during the holiday season.

Come December 1st, we each take turns doing creative things with our little elf (named Cocoa). Finn is by waaaaay better at this little game than I am (seriously, how does he come up with these hilarious scenarios?!), but we have so much fun putting Cocoa in ridiculous situations around our house. It’s a tradition I look forward to every year.

Christmas Eve & Christmas DayCasey and Mike Finn for the holidays

It can definitely be difficult to split holidays when you’re married, but it’s especially difficult when you both have divorced parents (anyone ever see the movie 4 Christmases? Yes, that’s pretty much our life!). Luckily, we’ve found a good balance with our families.

We always do Christmas mass and dinner at my mom’s house. We’ll then sleep over and do breakfast with her. Christmas afternoon we head to Finn’s dad’s house, and Christmas night we go to my dad’s house. Finn’s mom and sister live in Houston, so sometimes they’re here for the holidays and we’ll all be together at my mom’s house on Christmas Eve. It’s a lot to juggle, but we make it work!

Bridget’s Christmas TraditionsFamily Photos for Christmas Cards

Family Photos

taking holiday family photos each year

The first tradition we like to check off our holiday to-do list is our annual family photo, which usually doubles as my mom’s Christmas card. Not everyone loooovvvesss this tradition, but we all appreciate when it’s over and we have a photo of all of us together to document the year.  We set a date we can all make (the hardest part!), use these tips to snap the photo, and try to finish up as quick as possible so we can celebrate dinner or an activity together.  And speaking of which, we have to get on it this year since we had a new member join the crew a few weeks ago… my sister had her second baby… and we have no group photos with baby Charlie included.

Holidays In The CityHoliday traditions in downtown Chicago

Throughout our entire life, we’ve always headed downtown to enjoy all of the amazing things that the city of Chicago has to offer during this time of year. Growing up we always thought it was so cool to stay downtown in a hotel! We’d go ice-skating, see the windows on State Street, and do all of the holiday things — it was magical! The last few years we still make it downtown for these holiday memories but haven’t stayed overnight in a couple years. My parents are still keeping the tradition alive by going and staying overnight with a few other couples. Our hope is that we will rekindle the overnight tradition once the babies are a little older.

Our Couple Traditionsholiday elf on the shelf for adults


Like Casey and Finn, we also do Elf on the Shelf throughout the month of December. Although our ideas are far less creative than those Finns! Our little guy is named Elfvis and he does make us laugh out loud throughout the season. Who knew something so simple could bring so much joy… even before baby Ben came along?

looking at christmas lights in the neighborhood

One night, we also fill up a big thermos with coffee or hot chocolate and drive around the suburbs looking at Christmas lights and listening to Christmas music. It’s such a simple tradition, but one we love because it allows us to unplug and just chat about the holiday season, what we’re looking forward to, and anything else holiday related. This is something we both did as kids and we can’t wait to bring Ben along this year… as long as we’re back by his bedtime. 😉

It’s A Wonderful Life

It's a wonderful life holiday tradition

Last, but not least, we try and watch It’s a Wonderful Life at least once before Christmas! For a few years, we went as a family and watched it at Music Box Theater (so fun!), but watching it at home counts too. I just love the message behind this classic, so seeing this as well as a few other holiday favorites always gets us in the spirit of the holidays!

Casey – Family Gift Exchange IdeasO'Halloran family Christmas card 2017

Sibling Gift ExchangeFamily gift exchange ideas with siblings

As adults, we’ve always done a secret Santa amongst all of my siblings and their significant others. We’ve used the website Elfster to randomly be assigned a person to buy for, and then we’ll each spend about $100 on that person. That worked really well for us for a few years, until we realized that we were all pretty much just buying one another $100 gift cards and there wasn’t much creativity involved. Now we do this…

Buy for a Family in NeedOperation Santa through the USPS

Last year, we decided to put all of that money towards a family in need through the USPS’s “Operation Santa”.  Low-income families write letters to Santa with their Christmas lists and you can go through and choose one to fulfill. Last Christmas, we found the most amazing letter from a family of a mom and 3 young boys on the south side of Chicago. We all “owned” a certain category (gifts for mom, clothing for kids, toys, wrapping, etc.) and all of us purchased our gifts. We then handed them off to my mom who is the ultimate present wrapper. The post office then ships the wrapped gifts directly to the family to get there before Christmas Day.

We absolutely loved this new tradition and kept chatting about how we wish we could see this family opening their gifts on Christmas morning. Our plan is to do this again this year because it felt so good and we certainly don’t need any more gifts ourselves.

Bridget – Family Gift Exchange Ideas

Family gift exchange ideas

Like Casey, we do a grab bag within my immediate family on Christmas morning. We use drawnames.com to randomly assign everyone in our family a person to buy for. We love this website because it allows us to put stipulations on who can get whom (like married couples can’t get each other or you can’t get the same person as you had the year before). Usually, we put a $100 limit on this grab bag. Then all you have to buy for is that ONE person. This year we changed it up and each person received 2 names, with a $50 limit each.

$10 Challenge

gifts for couples in this gift guide

Matt and I usually do the “$10 challenge” when exchanging with each other, meaning we can only spend $10 on each other. It sounds silly, but it’s actually one of my favorite traditions because finding the perfect gift for under $10 is always a fun adventure! As for Ben, we want to keep it as simple as possible for his gifts so we’re actually not giving him anything this year. Are we the worst?! We gave a few gift ideas of things he needs to both sets of grandparents and told everyone else that all Ben wants for Christmas is their love. And honestly, we really mean it. I’m sure things will be different next year when he’s less of a baby, but for now, less is more!

What Do You Do For The Holidays?!

Yearly traditions are our favorite part of the holiday season… even if they slowly evolve over time. We’d love to hear about your family traditions and family gift exchange ideas! We’re always open to new ideas and hearing what others do usually inspires us to try new things… and start new traditions. Leave them in the comments below so we can all learn together!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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