The Windy City is famous for many things—hot dogs “dragged through the garden,” Portillo’s iconic chocolate cake, pizza as deep as lasagna—but perhaps my favorite of the bunch is Chicago-style popcorn. The kooky blend of cheddar and caramel corn is a Midwest staple, popularized by Garrett Popcorn and embraced for its perfect balance of sweet and savory flavors. Growing up in the Chicagoland area, I looked forward to the annual tin, unhinging my jaw as wide as possible while scarfing it down by the fistful. These bars borrow that same winning combination, reimagined into a cookie fit for the holidays. Savory cheddar shortbread does double duty, acting as a crisp base while also getting crumbled into a rubble-like topping alongside puffed caramel corn. A thick layer of chewy caramel holds everything together. It’s an unexpected treat that’s sure to steal the show.
A true Chicago-mix popcorn is as much about color as it is flavor, so make sure to pick up the most orangey block of cheddar you can find. The deep color of the resulting shortbread will scream cheese even before you take a bite. I like to use an extra-sharp aged cheddar, which strikes the right balance between color and flavor, but any bright orange brick will do.
BAKER’S NOTE: Bake your streusel and shortbread base past the point of the usual golden brown. They should be deep in color, almost burnt orange. The long baking time intensifies the cheese flavor, giving the streusel and shortbread a frico-like flavor reminiscent of a Cheez-It Extra Toasty cracker or the crispy skirt that forms on a grilled cheese.
Recipe information
Total Time
30 minutes (plus 1 hour for chilling)
Yield
Makes 18
Ingredients
8
1¾
½
⅓
2¾
¾
½
1
Need to make a substitution?
Preparation
Step 1
Place racks in upper third and middle of oven and preheat to 350°. Lightly coat an 8x8" baking pan, preferably metal, with nonstick vegetable oil spray. Line with 2 sheets of overlapping parchment paper, leaving a generous overhang on all sides. Lightly coat parchment with nonstick spray. Process 8 oz. extra-sharp orange cheddar, coarsely grated, 1¾ cups (219 g) all-purpose flour, ½ tsp. baking powder, ⅓ cup (67 g) granulated sugar, and 2 tsp. Diamond Crystal or 1¼ tsp. Morton kosher salt in a food processor until cheese has almost disappeared into mixture and no large pieces remain. Add ½ cup (1 stick) chilled unsalted butter, cut into ½"-thick pieces, and process until combined and mixture holds together when squeezed in your hand. (Dough will look dry and crumbly at first but will eventually come together.)
Step 2
Add about two thirds of dough to prepared pan; press into an even layer across bottom with your hands. Crumble remaining dough over a parchment-lined baking sheet into dime-size pieces. Bake streusel on top rack and shortbread base on middle rack until streusel is golden brown and crunchy, 17–22 minutes, and shortbread is golden brown and firm, 32–38 minutes. Let both cool.
Step 3
Meanwhile, heat remaining ¾ cup (150 g) granulated sugar and ¼ cup water in a medium saucepan over medium, swirling pan if needed (do not stir), until sugar is dissolved and syrup is boiling, 5–7 minutes. If sugar crystals start to form on sides of pan, brush with a wet pastry brush to dissolve. Continue to cook caramel, swirling occasionally, until deep mahogany and wisps of smoke rise from the surface, 10–14 minutes more. (Watch it closely; it can go from perfectly caramelized to burnt quickly. It’s better to skew slightly over-caramelized than under.)
Step 4
Remove caramel from heat and immediately add remaining ¼ cup chilled unsalted butter, cut into ½"-thick pieces (be careful as it will foam vigorously). Using a heatproof rubber spatula, preferably with a long handle, stir vigorously until butter is melted (it may look curdled at this point). Add ½ cup sweetened condensed milk and remaining ¾ tsp. Diamond Crystal or ½ tsp. Morton kosher salt; stir until smooth. Pour evenly over cooled shortbread; spread with an offset spatula if needed. Immediately crumble streusel over, breaking up larger pieces (you want them chickpea-size). Scatter 1 cup caramel popcorn on top, then gently press both into caramel (be careful; it will still be hot). Chill at least 1 hour.
Step 5
Run an offset spatula around edges of shortbread, then lift out of pan with parchment and transfer to a cutting board. Cut into thirds; cut each third into 6 rectangles to make 18 total. (For clean edges, score bars with a thin, sharp knife, cutting through topping and caramel, then use a serrated knife to saw gently through shortbread.)
Do Ahead: Shortbread can be made 2 days ahead. Cover and keep chilled.