See Chicago West’s Adorable Transformation Into Sister North West
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.
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Say Cheese
Chicago and Kim pulled some funny faces in this sweet post-Christmas selfie.
Instagram/@kimkardashian
Sibling Selfie
Saint hilariously managed to photobomb his mom and sister’s selfie.
Instagram/@kimkardashian
Pool Day
The mother-daughter duo swam off the winter blues during a fun pool day in December 2022.
Instagram/@kimkardashian
Sleepy Head
Chicago and brothers Saint and Psalm are a bunch of sleepy heads in Kim’s hilarious Instagram pic.
Instagram/@kimkardashian
Cousin Besties
According to Kim, Chicago and cousins True and Dream are “BFFAE best friends forever and ever.”
Instagram/@kimkardashian
Big Sister
“Chi & Psalm,” Kim captioned this sweet pic of her two youngest, complete with a pink heart emoji,
Instagram / Kim Kardashian
Sing It Loud
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.
Christmas Treats
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.
Girls’ Day Out
Kim took Chicago to San Francisco’s Asian Art Museum in Dec. 2021.
TikTok
TikTok Twins
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.”
Britney’s Biggest Fan
Yes, that is a vintage Britney Spears t-shirt that Chicago’s rocking!
Getting Shady
Kisses from mom! The mother-daughter duo posed for this snapshot in Aug. 2021.
Mother Stretch My Hands
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.
Lesson Plan
Kim encouraged Chicago to think about why people have palms. “To squish things!” Chicago exclaimed.
Cuddle Time
The sweet tot had a cuddle session with Kim after she playfully squished Chicago’s cheeks.
Cutest Clutch
“Caught someone trying to sneak off with my stuff,” Kim captioned an adorable pic of Chicago carrying a clutch with heart emojis in June 2021.
Fashion Forward
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.
I Scream, You Scream
Saint and Chicago are too cute with matching shouts in a sweet May 2021 pic.
Brother-Sister Time
“OMGGGGG,” mom Kim captioned an adorable sibling snapshot in May 2021.
Fun in the Sun
Chicago gives a model pout while Kim looks radiant in a sun-filled pic from Psalm’s 2nd birthday party in May 2021.
Instagram/Kim Kardashian
Matching With Mom
Chicago twins with mom Kim on Spring Break 2021.
Instagram/Kim Kardashian
Kim’s Twin Forever
Kim captioned this photo series, “My twin forever”
Instagram/Kim Kardashian
Cuddles With Chicago
Chicago beams as mom Kim scoops her up into a big hug.
Matching Again
Alongside this photo, Kim wrote, “3 out of 4.”
Playing Around
A perfect afternoon for Chicago? Spending time outside with her L.O.L. Surprise! dolls, of course!
Fashion Show
Some wear bathing suits near the sand. For Chicago, she would prefer a dress from one of her favorite Disney Princesses.
Kim Kardashian/Instagram
Baby Bro
Chicago West and Psalm West all bundled up in Dec. 2020.
Happy Birthday, Dream!
Kim wished Rob Kardashian‘s daughter Dream a happy birthday with this sweet photo and even sweeter caption. “My little baby Dream,” the KUWTK star wrote. “You are such a light! You are the best friend my babies could ever ask for! I love you so so much!!!”
Chicago & Dream
Cousins make the best of friends.
Matching Siblings
“These Two,” Kim wrote on Instagram in Oct. 2020, “Are Best Friends For Life.”
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