Our family vacation this year was a road trip from our home in Maryland to Chicago, so I thought it would be fun to find books with a connection to this famous metropolis.
Al Capone Does My Shirts, by Gennifer Choldenko (Best Book for Young Adults 2005, 2005 Audiobook for Young Adults). Although NOT set in Chicago, but rather on Alcatraz Island, near San Francisco, the title character was of course famous for his illegal rule of the Windy City. Since we had the fun of eating deep-dish pizza at The Exchequer, known for being one of Capone’s haunts, I couldn’t 
resist including this title. The story actually focuses on Moose, a twelve-year-old who’s forcibly moved to Alcatraz when his father takes on a guard job there, but the historical details provide some interesting insights on the era when Capone was active.
An Abundance of Katherines, by John Green (2007 Printz Honor Book). Ok, main character Colin Singleton starts this story by needing to get out of Chicago, after he’s dumped by his 19th girlfriend named Katherine. Still, between the road trip and the pictures of his early life around the University of Chicago, the book came to mind when I visited the city myself.
Divergent, by Veronica Roth (2012 Teens’ Top Ten, 2012 Best Fiction for Young Adults). I admit it, I haven’t read this series yet. But now that I know it takes place not just in some abstract future, but in Chicago of the future, I will have to get started. If you are one of the few who, like me, haven’t read it yet, Divergent and its sequels follow the story of Tris, a girl who, on her sixteenth birthday decides to change her “faction” from Abnegation to Dauntless. Hunger Games-like tests follow, along with chilling revelations about her society.
The House on Mango Street, by Sandra Cisneros (Outstanding Books for the College Bound, 1997 Popular Paperback for Young Adults). A short collection 
of vignettes follows Esperanza Cordero’s childhood in Chicago, her life in the house that her parents are very proud of, but that doesn’t feel like home to her. The stories read almost like poetry, and the descriptions are as vivid as a film clip.
Standing Against the Wind, by Traci L. Jones (2007 John Steptoe New Talent Award). This story follows Patrice, a young teen who is trying to get away from her inner-city Chicago life by winning a scholarship to a prestigious boarding school. Although it shows many of the difficulties that kids like Patrice face on a regular basis, it has a hopeful tone.
Yummy: The Last Days of a Southside Shorty, by G. Neri and illustrated by Randy DuBurke (2011 Quick Pick for Reluctant Readers, 2011 Great Graphic Novel for Teens). This intense graphic novel gives a sadder picture of Chicago life, with the portrait of a real gang member (Roger “Yummy” Sandifer) who lived and died in the 1980s. The book portrays Yummy’s life from the point of view of a fictional neighbor, and it refuses to offer any pat answers to the tragedy of gang involvement.
I’m sure I’ve just scratched the surface of YA books that have a connection to Chicago. What have I missed that I should read right now?
Where have you traveled this summer, either in person or via literature? Please share in the comments below!
-Libby Gorman, currently reading The False Prince by Jennifer A. Nielsen
I travelled to Vancouver BC and went in a week long cruise on Alaska’s inside passage. Amazing scenery and wildlife!
That does sound amazing! And I’m sure you beat the summer heat that way, too.
I have Chicago-land scifi-horror-survival-suspense titles for you!
In the After by Demitria Lunetta
The Girl Who Owned a City by O.T. Nelson and Dan Jolley (this one is a graphic novel)
Dust by Joan Frances Turner
These sounds very interesting–thank you!
If you have not already read Perfect Chemistry by Simone Elkeles, you must! When Chicago golden girl Britany meets bad boy Alex Fuentes, watch out!
Ooh, very intriguing!