1. The Chocolate Money, Ashley Prentice Norton (Mariner, $16)
Addictive as chocolate, this mildly disturbing debut novel about a Chicago heiress and her impressionable daughter has an extra dose of authenticity: The author is the daughter of Chicago philanthropist Abra Prentice Wilkin and the great-great-granddaughter of John D. Rockefeller. Sept. 18. RELATED: Ashley Prentice Norton on ‘The Chocolate Money,’ Being a Rockefeller, and Returning to Chicago »

2. The Signal and the Noise: Why So Many Predictions Fail–but Some Don’t, Nate Silver (Penguin, $28)
Another debut, this from the U. of C.–trained statistician who made his name with the PECOTA system that predicts how baseball players perform. Sept. 27

3. Building Stories, Chris Ware (Pantheon, $50)
The Oak Park cartoonist’s long-awaited release is a boxed set with 14 works. Oct. 2

4. The Middlesteins, Jami Attenberg (Grand Central, $25)
This funny and insightful novel by a Buffalo Grove native chronicles the unraveling of a decades-long marriage. Oct. 23

5. You Were Never in Chicago, Neil Steinberg (University of Chicago Press, $25)
In this love letter to our city, the Sun-Times columnist intersperses essays about his own Chicago history with essential tidbits for living here. Nov. 15

Photography: (The Chocolate Money) Courtesy of Houghton Mifflin Harcourt; (Building Stories) Chris Ware/Pantheon Books; (The Middlesteins) Courtesy of Grand Central Publishing