The Meaning Behind “Chicago” by Michael Jackson and the King of Pop’s Guilty Romance

Michael Jackson’s single “Chicago” has surged on the charts this year thanks to the 2026 biopic Michael. Released posthumously in 2014, the song was written by Cory Rooney and produced by Rooney, Jackson, Timbaland, and Jerome “J-Roc” Harmon.

In the song, Jackson falls in love with a girl but soon finds out that not everything is as it appears.

Dear Chicago

Jackson, traveling to Chicago, meets a woman and instantly becomes smitten.

I met her on my way to Chicago,
Where she was all alone.
And so was I, so I asked her for her name.
She smiled and looked at me,
I was surprised to see,
That a woman like that was really into me.

He pities her. She tells Jackson she’s a single mother and lonely. And in peak 90s fashion, Jackson pages the girl. But it soon becomes known that she’s, in fact, not alone or single.

She said she didn’t have no man,
Raised her kids the very best she can. (She’s loving me.)
She told me she was all alone,
Sad at home, she didn’t have no one. (She’s wanting me.)
She said just to give her a page,
Fifty-nine was the code she gave. (She’s loving me.)
She’d lied to you, lied to me,
’Cause she was loving me, loving me, yeah.

Her Words Seemed Sincere

The King of Pop was duped. He thought the heavens had sent an angel, but instead, the girl was cheating.

I never would’ve thought she was living like that,
Her words seemed so sincere.
When I held her near, she would tell me how she feels.
It felt so real to me, this girl, she had to be,
An angel sent from Heaven just for me.

Jackson is racked with guilt, and his emotions quickly turn to shame.

I didn’t know she was already spoken for,
As I’m not that kind of man.
Swear that I would’ve never looked her way,
Now I feel so much shame.

Still, Jackson did once say that the whole world has to answer right now just to tell you once again, Who’s bad!

Photo by Steve Granitz/WireImage