Illinois restaurant worker Alyssa Smith missing after vanishing on Chicago trip with boyfriend

An Illinois woman is missing after she vanished while on a trip to Chicago with her boyfriend, who then returned home alone, according to her family.

Alyssa Smith, 24, was reported missing on Sept. 30, Palatine cops said on Monday – three days after she last had contact with her mom, Rebecca Smith.

Smith, a Chipotle Mexican Grill worker, was last seen in Chicago’s 11th district “somewhere between Cicero, Pulaski and Madison,” according to a missing person’s appeal shared on Facebook. 

Smith, who has a “Pennywise clown tattoo on her shoulder,” was wearing a gray hooded sweatshirt, light khaki-colored pants, and white Adidas shoes at the time of her disappearance, cops said.

The circumstances behind Smith’s disappearance remain unclear.

Smith was traveling in the Windy City with her boyfriend, Jacob Ray Caso, some 30 miles from her hometown of Palatine.

Caso, a tattoo artist in Crystal Lake, returned home without his girlfriend of 20 months on Oct. 1 and searched the area where she was last seen, Smith’s mom revealed. 

Palatine police said they’ve received reports that Smith was possibly spotted in Grant Park in Downtown Chicago and Chicago’s West Side.

Smith’s family members shared missing person posters that ominously mentioned Smith having a “possible black eye, but police didn’t confirm the markings.

Caso has posted desperate appeals online amid the search for Smith, which has entered its second week.

“Time to come home b,” he wrote in a Facebook post Friday. “No one is mad at you.”

He has shared posters that claim Smith was identified from a TikTok video, without providing extra context. 

A post shared on Wednesday claimed an anonymous tip of Smith being found alive had been submitted. Palatine Police have not provided any further update.

Despite the reports of potential sightings, Smith warned her daughter is “still missing.”

“Until Alyssa is physically located and can speak for herself and tell authorities and her family that she is safe and does not wish to return home or have contact, we will continue to consider her missing and continue looking for her,” she wrote online, urging social media users to stop “debating the circumstances [of her disappearance] in the comments.”

“Until Alyssa herself is found and her safety is confirmed, we will keep looking.”

Smith’s disappearance comes less than nine months after marking one year of dating Caso. Caso and Smith have been dating since Jan. 21, 2025. 

“I can’t believe I’ve been with this old guy for a year now,” Smith said in a Feb. 2 Instagram post, celebrating the occasion.

“I love you so much and I can’t wait to see what the future brings us.”