I'll Take Everything You Have by James Klise

From an Edgar Award-winning author, this historical noir novel follows the life-changing summer of sixteen-year-old Joe Garbe as he discovers queer community in 1930s Chicago and gets caught up in the city's crooked underbelly.
 
In the summer of 1934, Joe Garbe arrives in Chicago with one goal: Earn enough money to get out of debt and save the family farm. Joe’s cousin sets him up with a hotel job, then proposes a sketchy scheme to make a lot more money fast. While running his con, Joe finds himself splitting time between Eddie, a handsome flirt on a delivery truck, and Raymond, a carefree rich kid who shows Joe the eye-opening queer life around every corner of the big city.
 
Joe’s exposure to the surface of criminal Chicago pulls him into something darker than he could have imagined. When danger closes in—from gangsters, the police, and people he thought were friends—Joe needs to pack up and get lost. But before he can figure out where to go, he has to decide who he wants to be.
 
I’ll Take Everything You Have is a vivid portrayal of queer coming of age in Depression-era Chicago, and a timeless story of trying to make your future bright when the rest of the world is dead set on keeping it hidden in the dark.