Obejas was born June 28, 1956 in Havana, Cuba. After emigrating to the United States at the age of six, she lived in Michigan City, Indiana and attended Indiana University from 1977—1979, when she moved to Chicago.Beginning in 1991, she was a reporter, and later, a freelance entertainment writer for the Chicago Tribune and other publications. She earned an M.F.A from Warren Wilson College in 1993 . She was the Springer Lecturer in Creative Writing (2003—2005) at the University of Chicago, as well as an advisor for the online prose magazine, Otium.

In fall of 2005, she served as the Distinguished Writer in Residence at the University of Hawai'i.

As of 2006, she is the Sor Juana visiting writer at DePaul University.

In 2008, she translated Junot Diaz's Pulitzer-prize winning novel, The Brief and Wondrous Life of Oscar Wao into Spanish.

We Came All the Way from Cuba So You Could Dress Like This?

This collection published in 1994 are fictional stories that take place in Chicago, many of which portray Latina lesbian refugees with short stories concerning “refugees and exiles of all ilks” Cuban refugees, junkies, homosexuals and AIDS victims. Reviewers have described We Came All the Way from Cuba So You Could Dress Like This? as “down to earth” and “the writings of the disenfranchised.”

Memory Mambo

Published in 1996, Obejas’ first novel concerns Juani Casas, a 20 something Cuban-American lesbian living in Chicago. This novel explores the themes of family, memory and identity that she focused on in We Came All the Way from Cuba So You Could Dress Like This? Publisher’s Weekly described Obejas’ prose as “illuminating and honest”.

Ruins

This novel published in 2009 “penetrates to the very heart of the Cuban paradox” takes place in 1994 during the Special Period in which anyone wishing to leave Cuba is able to leave. The hero of the story, Usnavy, remains dedicated to the revolution as the Havana that he knows literally crumbles around him. He has one treasure that consumes him; an extraordinary stained glass lamp that was his mothers and is possibly a real Tiffany lamp. With Ruins Obejas “confronts the fate of those who escape to the United States, and those who remain (as well as) broad issues of religious and sexual identity.”

• "Havana Luna " (2009) Akashic Books
• Ruins (2009) Akashic Books
• Havana Noir (2007)
• This is What Happened In Our Other Life (2007)
• Days of Awe (2001)
• Memory Mambo (1996)
• We Came All the Way from Cuba So You Could Dress Like This? (1994)

In 1999 and 1998, Obejas has shared a Peter Lisagor journalism award for pieces written for the Chicago Tribune, where she was a freelancer.10Obejas has won the Lambda Literary Award in the lesbian fiction category for Memory Mambo in 1997 and Days of Awe in 2002.In 1986 Obejas was a National Endowment for the Arts poetry fellow.