Years ago, I wrote a Sun-Times story about the food prepared by inmates at Cook County Jail, where I’d been offering pro bono creative writing classes. The food inmates prepared was sad stuff like pizza made of crumbled crackers, ketchup, and cheese sticks or a salad of crunchy ramen noodles and mayo. This inmate-prepared food was likely not much better than what was being served to them every day, but it was theirs, they made it and they owned it. People sometimes prefer food that is simply their “own,” food that maybe few others have and maybe no one else wants, but something special and ultimately theirs.

This need to create something special and one’s own may explain such Chicago culinary curiosities as the Jim Shoe (a sub of roast beef, corned beef and gyros, with yellow mustard and tzatziki sauce) and the Mother-in-Law (a corn roll tamale in a hot dog bun, covered in chili).  Another motivation could include the urge to make the most of limited resources; when you don’t have much to work with, you work with what you have.

Either of these two motivations – the need to make something of one’s own and the necessity of creating a “new” food from limited resources – likely accounts, at least in part, for cinnamon roll and chili, a Nebraska road food one-two punch.

As of October 1, the Runza food chain, founded in Nebraska, began serving the cinnamon roll and chili combination in addition to their namesake runzas, bread rolls traditionally stuffed with ground beef and cabbage, but open to being filled with whatever you got.

Recently, we traveled through Nebraska, but it was before October 1, and we couldn’t locate any place that was serving this combo. So, once we got home, we made some chili and bought a beautiful cinnamon roll, big as a softball, from Oak Park’s Spilt Milk (103 Oak Park Ave.).

The combination of cinnamon roll and chili *could* work. There’s frequently cinnamon in the chili recipes which could match up with the cinnamon in the roll, and the sweetness of the chili roll could play off any capsaicin heat in the chili. For our tasting, and to test the theory, it would have done us well to up the cinnamon and chile quotient in the chili. As it was, eating these two disparate foodstuffs together did little to enhance the flavors of either. That said, there’s potential deliciousness in the combo that careful preparation of both components could make a reality.

My guess is that there may be something else that explains the popularity of the cinnamon-chili combination platter: nostalgia. It’s my understanding that this meal is popular in the school cafeterias of Nebraska and some other Midwestern states; this makeshift combo meal could simply be the result of kids playing around with flavor combinations and finding something they like, then someone takes notice and it becomes a “thing.” An analogy is the childhood habit of dipping French fries into a chocolate shake, a flavor combo Phillip Foss conjured at El Ideas, or the peppermint-stick-in-a-pickle enjoyed by youngs on Chicago’s southside.

I’ve seen photos of cinnamon rolls and chili being served as two separate dishes and with both ingredients combined into one dish, and there is some disagreement about the “correct” way to eat both items: either sequentially, with the cinnamon roll for dessert, or simultaneously, by alternating bites, by using the torn roll as a dipper or spoon, or by combining both in one bowl which, I must say, borders on the repulsive.

Cinnamon rolls and chili are reportedly eaten together in Midwestern states like Missouri, Iowa, and Kansas, but also Colorado, Washington state and other regions. It seems never to have been a big thing in Illinois.

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David Hammond

David Hammond, a corporate communications consultant and food journalist living in Oak Park, Illinois, is a founder and moderator of, the 8,500 member Chicago-based culinary chat site. David...