Due to her academic intelligence, Obama was presented with the opportunity to enroll in Chicago's first magnet high school, Whitney M. Young Magnet High School. As a student here, she took advanced-placement classes, was a member of the National Honor Society and served as treasurer of Student Council. She graduated in 1981 as salutatorian.

One would think that with those accolades, it would be enough to attend one of the most prestigious universities in the country. According to Obama herself, her high school guidance counselor seemed to think otherwise.

"'I'm not sure,' she said, giving me a perfunctory, patronizing smile, 'That you're not Princeton material,'" the she wrote of the administrator in her 2018 memoir Becoming. 

Though she doesn't recall the woman's age or race, she used that criticism to power her way through an acceptance into an Ivy League school.

"I wasn't going to let one person's opinion dislodge everything I thought I knew about myself."

Following her 1981 graduation from Whitney M. Young Magnet High School, Obama went on to follow in her older brother Craig's path and enrolled at Princeton University, graduating cum laude in 1985 with a Bachelor of Arts in Sociology and African-American studies.

In Becoming, Obama detailed her experience attending the Ivy League institution. 

"It was impossible to be a Black kid at a mostly white school and not feel the shadow of affirmative action. You could almost read the scrutiny in the gaze of certain students and even some professors, as if they wanted to say, 'I know why you’re here.' These moments could be demoralizing, even if I’m sure I was just imagining some of it," she penned. "It planted a seed of doubt. Was I here merely as part of a social experiment?"

Though the mother of two didn't mention much about the financial strains of undergrad, she did note her family "never once spoke of the stress of having to pay for college, but I knew enough to appreciate that it was there."

However, she did reveal she earned a financial aid package with the stipulation of holding a work-study position. Throughout her time in New Jersey, she was worked as an assistant to the Third World Center, a support office for scholars of color that she depicted as "poorly named but well-intentioned."

Obama was accepted and enrolled at Harvard Law School immediately after graduating from Princeton, earning her J.D. in 1988. In an interview with Refinery29 for International Women’s Day in 2018, she championed the benefits of education.

"Education also grants us a fighting chance. We are constantly being beaten down by the multiple layers of systems that oppress us. We live in a world that sexualizes us for being women and ostracizes us for being Black. So education is a Black girl’s weapon. Audre Lorde, Alice Walker, and Kimberlé Crenshaw couldn’t create terms like Black feminism, womanism, and intersectionality to spread the word about our struggle without that knowledge."

Obama returned to Chicago following graduation and worked as an associate at the firm Sidley Austin in the marketing and intellectual property department, per the White House archives.

She has said she remembers the difficulties she faced coming from a family with limited education.

"I personally know how life can treat you when you don’t have an education — I’ve seen the cost my mother paid for being illiterate. But she never complained, and even when she was sick or needed help with chores, she always said, ‘Focus on your studies.’ She knew the value of education.”