The inaugural Chili Bowl was organized by Lanny Edwards and partner Emmett Hahn.[5] It was named after a local company who sponsored the first event.[5]

The inaugural 1987 event consisted of 52 midgets competing in the two-day event.[6] The event now consists of five days of qualifiers for the Saturday night A-main event, with over 341 cars entered for the 2020 race.[7] One fifth of the drivers compete in each qualifying night's event, attempting to qualify for the A-main.[7] Each qualifying night has heat races, dash-type events, and a 25 lap feature.[7][8] Drivers who finish poorly in their heat event in their qualifying night start deep in final night qualifying events and have to finish high in many events to make the A-main field. A driver who started in the lowest "P" event would have to finish high in P, O, N, M, L, K, J, I, H, G, F, E, D, C, and B events to reach the A-main. The top two finishers in the qualifying night's feature event, plus the top seven finishers from the two Saturday night B-main events will progress into the Saturday 40-lap A feature, with a field of between 24 and 26 cars.

The event also has rewards for winning. The winner of the second-night Race of Champions between past Chili Bowl winning drivers, drivers nominated by former race champion teams, and the reigning national Midget Driver of the Year will be awarded a guaranteed starting position. If the driver who won the preceding year's Chili Bowl or the Race of Champions fail to qualify, they are added as the 25th and 26th cars in the field.

The National Midget Auto Racing Hall of Fame uses the event to induct its next class of members.

Originally, the event was held in the week ending on the second Saturday of January. Since 2009, the event usually ends on the third Saturday of January.