When Superintendent Chalmers is selected to give the keynote speech at an administrators' convention in Cincinnati, he elects to take popular Principal Finch as his plus one.
During detention, Bart notes the school's lack of respect for Principal Skinner and urges him to step up his game to win the spot.
When Finch falls ill from food poisoning, Skinner volunteers in his place, and Chalmers reluctantly agrees.
Things get off to a rocky start when Skinner checks the bag with Chalmers's anxiety medicine at the airport, causing him to have a panic attack and get thrown off the flight.
The pair face a number of obstacles, including a hitchhiking Shakespearean improv, a traffic court and an angry gang of cyclists; but eventually begin to bond.
However, he is able to bond with the other superintendents over tales of inept underlings, and ends up praising Skinner, who has just arrived to deliver the notes.
Upon returning to Springfield, Skinner earns the respect of the schoolchildren and meets with Chalmers for a friendly meal at a chili restaurant.
Executive producer Matt Selman wanted to explore the Skinner-Chalmers relationship with a road trip episode.
As part of the research, the producers ordered a large box of Skyline Chili through the mail, which came in cans and bags.
In the final animation, Selman noticed that Skinner and Chalmers were eating Cincinnati chili out of bowls instead of plates, but it was too expensive to reanimate.