Chicago singer Elliot Henderson's alleged travel scam drama explored as police take action after multiple complains from clients

Popular Chicago singer Elliot Henderson has come under fire for an alleged countrywide travel scam, as reported by CBS News. He was accused of swindling money from innocent victims by telling his clients that he operated a travel business and had connections in the industry. He would offer travel packages to his victims including flights, hotels, play tickets, and other services at an attractive price.

However, these services never came to fruition and the singer pocketed the cash he received from his victims. Some victims were left stranded and had to cough up more money just to stay in a hotel the scammer allegedly claimed he booked but in reality did not. Henderson was arrested during a Valentine's Day performance this year.

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The many alleged scams of Elliot Henderson

Chicago singer Elliot Henderson is being accused of selling people dreams and then ripping them off. An investigation conducted by The Shade Room (TSR) went into detail about how the man allegedly swindled money from a plethora of innocent individuals. One of those individuals was Christina C from Baltimore who told TSR that Henderson knew how to "spit game".

Christina, who heard about Henderson's travel offers through a family member, bought a travel pass with bundled airline tickets from Henderson for an Atlanta trip. Elliot Henderson claimed that he had corporate connections with a prominent airline and the price he offered for the passes was $1250 and this could be broken down into payments. Christina paid him an initial payment of $500.

Christina went from Maryland to Atlanta without any hiccups but was hit with a major problem when Henderson failed to come through on the flight back to Maryland and her hotel room. He allegedly kept stalling using a plethora of excuses regarding why her flight to Atlanta wasn't being confirmed.

The credit card Henderson used to reserve a hotel room with $150 from Christina was not paid for, meaning Christina had to pay $329 to get her own room. Henderson claimed that he would pay her back and used a barrage of similar excuses but Chistina ended up buying a 13-hour bus ticket back home.

Henderson even sent Christina an apology text and claimed that he couldn't send her money because he was maxed out for the day on his credit card but he was allegedly using fake receipts. Christina's family also canceled their various trips with Henderson once they found out about her experience.

Another woman, Crystal G told TSR that she booked a five-star hotel with Elliot Henderson for a birthday trip but was kicked out after two nights due to non-payment. She had to pay a further $800 just to stay there. Trina Wallace sent Henderson $600 twice to reserve him and his band at a jazz lounge. Henderson charged an extra fee for an appearence by Lalah Hathaway but the latter never showed up.

A plethora of other victims of Elliot Henderson came forward to share their stories to a CBS Chicago investigation earlier in March. One woman named Pinky Jackson booked a hotel room and Hamilton play tickets from Henderson but both the tickets and the hotel reservation were invalid.

Another woman named Jasmyne Franklin lost $36,000 by investing in Elliot Henderson's travel business. However, she never got the returns and received an invalid Western Union receipt after asking for a refund multiple times. Franklin later filed charges against Henderson with the Streamwood Police in March of last year.

After failing to appear at the police department and paying back Franklin, Elliot Henderson was eventually arrested in February of this year during a Valentine's Day performance.

Henderson told The Shade Room that a lot of people had successfully booked travel packages with him but unfortunately, a few of his airline connections faltered causing a trickle effect. He promised the outlet that he was working on paying back his victims via payment plans.