Chicago West is halfway to double digits.
The Kardashian-Jenner grandkids continue to grow up before our very eyes, as Kim Kardashian and ex-husband Kanye West's third child officially turned 5 on Jan. 15.
Chicago was welcomed into the world in 2018, just a few years after older brother Saint was born in 2015. And just like big sister North, Chicago would also take on the big sister role with the birth of little brother Psalm in 2019.
Thanks to her family—including aunts Khloe Kardashian and Kourtney Kardashian and grandmother Kris Jenner—fans have gotten an inside look into Chicago's childhood, from holiday celebrations and sibling snuggles to play dates with cousins True Thompson, Dream Kardashian and Stormi Webster.
In honor of her big day, we're taking a look back at her cutest photos over the years, all the way from her first appearance in Kyle Jenner's 2018 pregnancy announcement video to her recent post-Christmas selfies with Kim and Saint.
Scroll below to see all that and more adorable moments.
Girls' Night Out
All Chicago West wanted for Christmas was to attend Mariah Carey's holiday concert with her family and she did just that in November 2023.
Kim Kardashian brought Chicago and her oldest daughter North West to the pop star's Merry Christmas One And All! tour show at the Hollywood Bowl Nov. 17, and was accompanied by Khloe Kardashian, her daughter True Thompson and Rob Kardashian's daughter Dream Kardashian. Plusm Momager Kris Jenner also joined in on the girls' night out.
Cheeky Cousins
Chi and True paid tribute to their mogul moms in an adorable and mischievous way in July 2023 when they sporting black T-shirts bearing collages of photos of Kim and Khloe.
The Good American founder captioned her Instagram post, "They think this t-shirt thing is funny."
Hi, Barbies!
The Kardashian fam proved life in plastic is fantastic when they enjoyed a girls trip to the World of Barbie immersive experience last June.
Kim and Khloe brought Chicago, True, Dream and Kylie Jenner's daughter Stormi Webster along for the Barbie-themed outing, with all of the cousins wearing pink ensembles.
A Purrfect Party
To celebrate Chicago's fifth birthday last January, Kim held a Hello-Kitty themed party.
The SKIMS founder shared video from the special occasion on TikTok, including signs of Hello Kitty wearing a necklace that said "Chi" on it, and pink balloons.
The celebration also featured a slime-making station, a table to decorate your own Hello Kitty ceramic, a face painting station and a slide leading into a pink ball pit.
Chicago and Kim pulled some funny faces in this sweet post-Christmas selfie.
Saint hilariously managed to photobomb his mom and sister's selfie.
The mother-daughter duo swam off the winter blues during a fun pool day in December 2022.
Chicago and brothers Saint and Psalm are a bunch of sleepy heads in Kim's hilarious Instagram pic.
According to Kim, Chicago and cousins True and Dream are "BFFAE best friends forever and ever."
"Chi & Psalm," Kim captioned this sweet pic of her two youngest, complete with a pink heart emoji,
Chicago, 4, sings her dad Kanye West and XXXTENTACION's song "True Love" while sitting in a vehicle with her little brother Psalm West, 3.
Don't be fooled—Chicago had to work for this candy cane! Kim shared an adorable video of the three-year-old trying to convince her that she should be "allowed" to have the treat before the holidays.
Kim took Chicago to San Francisco's Asian Art Museum in Dec. 2021.
ICYMI, North West is a TikTok star! Chicago made a cameo in one video as the sisters rapped along to Eminem's "The Real Slim Shady."
Yes, that is a vintage Britney Spears t-shirt that Chicago's rocking!
Kisses from mom! The mother-daughter duo posed for this snapshot in Aug. 2021.
Chicago took a lesson from her dad's songbook and asked mom Kim about the anatomy of a hand in an adorable video, shared Aug. 19.
Kim encouraged Chicago to think about why people have palms. "To squish things!" Chicago exclaimed.
The sweet tot had a cuddle session with Kim after she playfully squished Chicago's cheeks.
Chicago is wearing red cowboy boots and a studded denim jacket in a very chic pic alongside older brother Saint. "I am done," aunt Khloe commented with heart-eye emojis in May 2021.
Saint and Chicago are too cute with matching shouts in a sweet May 2021 pic.
"OMGGGGG," mom Kim captioned an adorable sibling snapshot in May 2021.
Chicago gives a model pout while Kim looks radiant in a sun-filled pic from Psalm's 2nd birthday party in May 2021.
Chicago twins with mom Kim on Spring Break 2021.
Kim captioned this photo series, "My twin forever"
Chicago beams as mom Kim scoops her up into a big hug.
Alongside this photo, Kim wrote, "3 out of 4."
A perfect afternoon for Chicago? Spending time outside with her L.O.L. Surprise! dolls, of course!
Some wear bathing suits near the sand. For Chicago, she would prefer a dress from one of her favorite Disney Princesses.