Meaning of “Chicago” by Michael Jackson

Written By Michael Miller

Michael is a music teacher and professional cellist. He loves uncovering the deeper meaning of popular songs.

“Chicago” is a tale of unexpected romance, betrayal, and realization. At its core, it recounts a chance encounter between two strangers that leads to a whirlwind relationship. But as the song unfolds, it’s revealed that this newfound love has a secretive, deceitful side. Michael sings about the woman’s dual life, the lies she tells, and his own feelings of regret upon discovering the truth. The song highlights themes of trust, deceit, and introspection.

Dive deeper, and you’ll see a captivating story of passion, secrets, and consequences. Sounds enticing? Keep reading.

“Chicago” Lyrics Meaning

As the song kicks off, Michael meets a woman in Chicago. She’s alone, and so is he. Their interaction starts off innocently enough, with him asking her name and her reciprocating with a smile. The first impression suggests a chance encounter that could bloom into something beautiful.

But as the lyrics progress, we see red flags. She tells him she’s all alone, doesn’t have a phone, and even hints at a secret communication code (“59 was the code she gave”). The repetition of “she was lovin’ me” emphasizes the intimacy they shared.

However, things take a turn with the poignant line, “She lied to you, lied to me, ’cause she was lovin’ me.” This reveals the woman’s dual life. She isn’t the lonely soul she portrayed. Instead, she’s entangled in another relationship, possibly with a family, thus betraying both Michael and her other partner.

The intensity ramps up in the bridge. Michael’s realization is heart-wrenching: “I didn’t know she was already spoken for… I swear that I would have never looked her way.” His regret and guilt are palpable. He thought he’d found love, but it was built on deception. By the end, he’s holding her accountable, a stark contrast to his initial enamored state.

Why Was “Chicago” Written?

To fully grasp “Chicago,” it’s essential to delve into the songwriter’s mindset. Michael Jackson, throughout his career, often touched upon complex human emotions, love, betrayal, and introspection. The King of Pop was no stranger to love stories with twists.

Given Michael’s own tumultuous personal relationships and the media’s scrutiny, it’s possible the song touches on the challenges of finding genuine connections. “Chicago” paints a vivid picture of the unpredictability of love, the hurt of betrayal, and the introspective journey one undertakes after being deceived. It serves as a reminder that not all that glitters is gold, and sometimes, the most enchanting stories have the most profound lessons.