The chili/cinnamon roll combo started in the public schools in northwest Iowa. On Fridays you either got tacos with cinnamon rolls or chili with cinnamon rolls. The rolls were made right in the schools typically and were delicious. Add to the combo two other very positive things - it was Friday and it was the only day of the week where chocolate milk was served - and you've got very powerful comfort food.
My wife and I have had a tradition of chili and cinnamon rolls on Christmas Eve since we got married. Here is how I make the chili. The emphasis is on subtle flavors.