Cousin Fun
Kylie Jenner shared a video of her daughter Stormi and niece Chicago trying out some skincare products after they went shopping at Ulta Beauty in December 2024.
Matching PJs
‘Tis the season to sport matching holiday pajamas and revel in and Elf on the Shelf antics as Chicago did with cousin True in December 2024.
Time for School
Kids—they grow up so fast. Kim Kardashian posted a pic of Chicago and her siblings Saint, Psalm and North getting ready for class in September 2024, writing, "school daze are upon us."
Sweet Dreams
Kim snapped a photo of Chicago taking a snooze in August 2024 and called her "my sleeping beauty."
Home
And in this picture posted in August 2024, Chicago cuddled with her mom Kim and brothers Psalm and Saint as the SKIMS mogul captioned it, "Home."
Summer Fun
North carried her little sister Chicago in this adorable snap of them celebrating "summer ‘24" with their mom and brothers.
Sisters
The August 2024 photo series also featured a photo of the two sisters drawing at the cabin during their summer getaway.
BFFs
Kim summed up Chicago's bond with Khloe Kardashian's daughter True in one word: "besties."
3 Generations
Kim shared a photo with "my girls"—including her daughters North and Chicago and mom Kris Jenner—in June 2024.
Almost Birthday Time
Just before Chicago turned 6 in January 2024, Kim uploaded a pic of her and her mini-me, writing, "It’s someone’s birthday sooooon."
Girls' Night Out
All Chicago wanted for Christmas was to attend Mariah Carey's holiday concert with her family and she did just that in November 2023.
Kim brought Chicago and her oldest daughter North to the pop star's Merry Christmas One And All! tour show at the Hollywood Bowl Nov. 17, and was accompanied by Khloe, her daughter True and Rob Kardashian's daughter Dream Kardashian. Plus, momager Kris 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.
Kim and Khloe brought Chicago, True, Dream and Kylie Jenner's daughter Stormi along for the Barbie-themed outing, with all of the cousins wearing pink ensembles.
A Purrfect Party
To celebrate Chicago's fifth birthday in 2023, 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.
Say Cheese
Chicago and Kim pulled some funny faces in this sweet post-Christmas selfie.
Sibling Selfie
Saint hilariously managed to photobomb his mom and sister's selfie.
Pool Day
The mother-daughter duo swam off the winter blues during a fun pool day in December 2022.
Sleepy Head
Chicago and brothers Saint and Psalm are a bunch of sleepy heads in Kim's sweet Instagram pic.
Cousin Besties
According to Kim, Chicago and cousins True and Dream are "BFFAE best friends forever and ever."
Big Sister
"Chi & Psalm," Kim captioned this sweet pic of her two youngest, complete with a pink heart emoji,
Sing It Loud
Chicago sang her dad Kanye West and XXXTENTACION's song "True Love" while sitting in a vehicle with her little brother Psalm.
Christmas Treats
Don't be fooled—Chicago had to work for this candy cane as Kim shared an adorable video of the then-3-year-old trying to convince her that she should be "allowed" to have the treat before the holidays.
Girls' Day Out
Kim took Chicago to San Francisco's Asian Art Museum in Dec. 2021.
TikTok Twins
ICYMI, North is a TikTok star! Chicago made a cameo in one video as the sisters rapped along to Eminem's "The Real Slim Shady."