🎅✨Santa! I know him!
I’m a Pisces, and gifting is absolutely my love language. I keep a running list on my phone all year of things I come across that I think people in my life would love, and I take gift-giving very seriously.
Every year, I still find the department-store decorations—while Bing Crosby croons for six weeks straight—completely magical. I ooh and ahh over the overpriced “special edition beauty gift bundles,” and I’m a sucker for equally overpriced wrapping paper.
I also spent my formative years as a full-on mall rat and worked every holiday retail job imaginable (Gap, Macy’s beauty counter, Express). I’ve worked the 6 a.m. and midnight shifts, gift-wrapping and packing FREE gifts-with-purchase until my fingers practically bled. Fun fact: my parents STILL have an Express Christmas tree from 2004 that was headed to the Springfield Mall dumpster—and it now proudly sits on their front porch.
All that’s to say: I’ve spent years immersed in the world of holiday gifting, and I hope you find this simple little guide inspiring—and maybe discover a few new brands along the way.
🛍 Shop By Categories
🎱 90’s Christmas
Build your own working Game Boy with Legos and comes with games
Even if it’s not a 90’s toy -the millennial childhood staple is back!
NGL I’m probably more excited about this gift than my kids will be!
Give the gift of 90’s tech with this OG Tamagotchi keychain
A portable and digital version of the classic toy, perfect for travel
This is a fun, mess-free craft I used to spend hours playing as a kid
Browsing through these pages is like catnip for ’90s nostalgia
Settle sibling drama, bonus that they glow in the dark.
Just like the ones we had as kids - perfect for holiday travel
A digital point-and-snap that gives that filtered Kodak look
The original sensory toy! Perfect stocking stuffer for all ages
Introduce your kids to a fixture of ’90s childhood with this bundle
📱 Best of the Group Chat
A portable and fun to use music and story player - for ages 3-12
A kid-friendly mahjong set to help young players learn
I can always count on Boden coats for quality and cool designs
A new game voted best game of 2025 by Parent magazine
An award-winning toy - a kid-friendly “makeup” kit that looks like moms
Perfect for the kiddo who loves AG and stickers - under $15
The viral web shooter featured on Shark Tank that glows in the dark!
A fun line of inflatable sleds in several different designs
Made in France, this polish is kid-safe and water-based
The perfect practical and fun gift for the ultimate Frozen fan
What can I say? What kids don’t love giggling about 💩 and bingo?
⭐ Shop Local: Chicago
The M+A Let’s Dance dress is a wardrobe staple in our house!
Play! has 5 locations, or you can shop online + free gift wrap!
This mom-owned local biz has tons of fun gifts for Swifties
This Lincoln Square gem has tons of unique and educational gifts
My go-to boutique for the cutest apparel for Chicago kids
One of my go-to gifting shops has a chic little kids’ section
This Bucktown toy store (since 1998!) has great STEM toys
Little Charm has the cutest apparel line with a Chicago teddy
We love this upscale consignment store that also carries retail gifts
Our favorite playplace in LaGrange has the coolest labubu gifts!
Give the gift of a super fun kids’ pottery workshop at MADE
Mish Market makes the sweetest gifts, like these kid duffels
🧷 Gifts for Baby
If you aren’t ready for the subscription model, this is a great option
This is a super fun gift that’s both educational and interactive
Babies love this tree, mom’s love this tree,
get the tree!
This is the perfect Trike for 3 and under with a sweet little basket
My little one was obsessed with this sensory game
This is a great price for an aesthetic activity baby table
Perfect for babies until they graduate to stealing your real keys
The softest socks that my sock-hating kids actually love
Create a board book with pics of all your baby’s favorite people
A sweet little under-the-sea toy that they can fill up with tiny treasures
These are the cutest heirloom stuffies that also give back
A plushy version of the OG girlies, now with a board book for baby!
🎁 Gifts for Older Kids
A fancier and elevated personalized friendship bracelet with stones.
The Polo Bear is the hottest commodity thanks to TikTok
Your kid will either love and treasure it or die of embarrassment
The viral hand sanitizer that’s on the wishlist of all my nieces
For the baseball lover, a fun way to show off all your ballpark visits
Even if they have smartphones, it’s still fun having a Polaroid
A clean skincare and beauty line for tweens/teens
For the kid who’s both a sneakerhead and still loves Legos.
A fun and affordable gift for the gal who’s Polo Bear obsessed
A digital handheld camera that looks like Super 8 film footage
For the kid who wants to turn their bead hobby into a small biz
Trust me when I say you can’t go wrong with a new Jellycat
📖 Holiday Books
The chicest mouse in Paris has a fabulous Christmas book
The perfect gift for your budding baker with kid-friendly recipes
A sweet illustrated holiday book from one of our favorite authors
A collection of holiday short stories with beautiful illustrations
This book comes with envelopes full of letters from Santa himself!
A sweet story from beloved children’s author Oliver Jeffers
A sweet story about a family of llamas celebrating Hanukkah
A fun story about a dog who ventures to the North Pole
A fun book for ages 3-5 that has an activity on each page
My 3-year-old is obsessed with trouble-making David!
A holiday companion to the beloved Chicka Chicka boom boom.
A YA holiday romance told in an advent calendar format
❣ Gifts for Mom
I have a vice of buying boogie candles, and this is by far my favorite
I swear by packing cubes, and I can’t resist a monogram
Another local business - they have the coolest mahjong mats
Treat yourself to a new cozy pair of sherling UGGS - love the bow
The perfect weekend loungewear that still looks chic
Everyone in my house fights over who gets this amazing blanket
Be the envy of all the Gen Z girlies with this coveted classic
Bobbi Brown’s clean makeup line is one of my new favorites
My favorite sunglasses brand has the coolest rainbow tortoise pair
The festive gift for cool moms who also love needlepoint
These petite plume wide-leg jammies are cozy and comfy
Alice and Wonder is my go-to shop for Chicago gear like cute hats
🎄 Gifts for Dad
Probably something he won’t buy himself, and great quality
This is a hybrid garment bag and duffel, perfect for travel
A great set to get the guy in your life to up his skincare game
Abercrombie’s NFL collection is for all ages, and Gen Z approved
Even if you have a Yeti, the cooler is super useful on the go
A great stocking stuffer that can also be monogrammed
The viral smart projector that can stream apps and project on anything
A book of movie night ideas for when dad’s in charge of the remote
Stylish and made for wearing while being active for $25
Perfect for the gamer dad who wants to game on the go
Clips right on your golf cart. This was a hit with my dad
A mini photo album that fits 100 pages and easy to customize
🫶 Gifts for Care Givers
The easiest gift - just upload a pic to create a custom photo ornament
A fun gift for under $25 and a screen-free way to unwind
The trend of 2025 - a gorgeous set of tiles makes a great gift
Upgrade Grandma’s pickleball game with a cute bag
A gorgeous floral ceramic frame - just add a cherished photo
The gift I give to everyone- in a range of sizes and prices
The viral glasses sell out every year - a great gift under $20
A great gift for grandparents to show off grandkids
The perfect gift for the person who loves to
plan in style
Pair with a bag of loose-leaf tea for a cozy winter gift
I gifted this to my grandparents with a painting of their home
Pair with a bag of loose-leaf tea for a cozy winter gift
I hope this guide brings a little magic to your holiday shopping and helps you discover something new.
If you haven’t yet, subscribe to Big Weekend Funletter so you never miss a gift guide or Chicago family find. 💌✨
