The former couple, who split after less than a year of dating in December, exited the Greenwich Hotel ‘separately’ but used the same side door, an eyewitness told DailyMail.com.
Their respective checkouts were ‘less than one hour apart.’
The 28-year-old model attempted to go incognito in a plain white t-shirt and black sweatpants following her fun-filled evening, which included three outfit changes.
She completed her sporty ensemble with a pair of white sneakers with black stripes, sunglasses and her hair pulled back in a sleek updo.
The Keeping Up with the Kardashians alum, who rose to fame on her family’s reality show before pursuing modeling at age 13, carried a large bag on her shoulder.
Meanwhile, her ex-boyfriend kept his hood pulled up and a baseball cap lowered on his face as he made his beeline to a car.
On Monday, Jenner sent the internet into a frenzy as she climbed the famous steps at the The Metropolitan Museum of Art in a butt-baring Givenchy gown.
Her show-stopping look marked the first of three stunning ensembles of the night as she proceeded to slip into two different minidresses the Après Met 2 Met Gala After Party.
As she let loose at the bash, hosted by Carlos Nazario, Emily Ratajkowski, Francesco Risso, Paloma Elsesser, Raúl Lopez of Luar, and Renell Medra, the Vogue cover girl was spotted mingling with Bad Bunny.
The duo looked smitten with one another as they sat side-by-side on the same couch and shared a drink.
In January, the pair reunited, weeks after their breakup, as they rang in the New Year together with mutual friends in Barbados.
‘Kendall and Bad Bunny aren’t petty and no drastic break up happened. You’ll see them together again and again, will it lead to them getting back together romantically or a friends with benefits, those options are on the table but right now nothing is official between the two,’ a source told DailyMail.com, at the time.
In mid-December, it was reported that Kendall and Bad Bunny, born Benito Martinez Ocasio, split after almost a year together.
A source told People that the duo are ‘no longer a couple,’ giving no details as to why.
Prior to their split, Kendall and Bad Bunny were last pictured together on October 29 while at breakfast in Beverly Hills, one day after they attended a Halloween bash together, per TMZ.
That sighting came after they attended an afterparty for Saturday Night Live in New York City on October 22.
Kendall and Bad Bunny first sparked rumors of a romance in February 2023, after they were seen out together on what appeared to be a double date with Justin and Hailey Bieber at Wally’s in Beverly Hills.
At the time, a source at People said: ‘Kendall recently started hanging out with him. They were introduced by friends. He moved to LA a few weeks ago and bought a home.’
‘She likes him and is having fun. He is different from guys that she dated in the past. He is very charming,’ the insider said.
Soon after, the couple were seen going horseback riding together in early April, cuddled up on a horse.
They were seen on a horse at the Hidden Hills Equestrian Center in LA.
Two weeks later, Kendall and Bad Bunny stayed close at Coachella Music Festival in California.
They were seen chatting and standing close in the crowds.
Bad Bunny performed at the festival, with Kendall also supporting him in the audience.
They also attended Met Gala afterparties together on May 1st, despite posing separately on the red carpet at the Metropolitan Museum of Art in the Big Apple.
On May 12th, the couple enjoyed a Lakers playoff game together while seated courtside; they appeared very flirty and happy together.
Kendall and Bad Bunny made a rare display of PDA in August at the Drake concert in LA.
The couple couldn’t keep their hands off each other, as they kissed, hugged and danced together in the crowd.
The lovebirds jetted off to Milan, Italy after holidaying in Idaho together.
They made their front row debut as a couple at the Gucci show in September, which also is the same brand they starred in a campaign for.
Previously, Kendall has dated Harry Styles, Devin Booker, Jordan Clarkson, Blake Griffin and Ben Simmons.
Prior to Jenner, Bad Bunny was romantically linked to Gabriela Berlingeri and Carliz De La Cruz.