I’m in Lincoln, Nebraska too and it is a minor religion here, serving cinnamon rolls with chili. I grew up eating school lunches in Cedar Rapids, Iowa. We had homemade school lunch lady chili and homemade cinnamon rolls, but not necessarily paired for the same meal.
Here a few grocery store bakeries fashion bread bowls out of cinnamon rolls for people to serve chili in. That’s a bridge too far for me.
Runza makes good chili, especially for a fast food place-it’s a local chain that has grown immensely. They also make Runzas, which they try to trademark (unsuccessfully), which are delicious-yeast bread shaped around a spiced ground beef, onions and cabbage filling. Very hearty and filling. I eat their chili when I get a hankering for chili, it’s reliably good. I never bother getting the side of cinnamon rolls to go with it, just never got attached to the pairing.