The episode title is a pun on "We love to fly, and it shows", an advertising slogan used by Delta Air Lines in the 1980s.
While in Chicago, Mr. Burns and Homer walk into a salon called "Ferris Bueller's Day of Beauty", a pun on John Hughes's 1986 movie Ferris Bueller's Day Off. When they exit the salon, they are dressed as Ferris and his friend Cameron, respectively.
In the chalkboard gag, Bart writes "I will not wait 20 years to make another movie", a reference to 2007 (the year of the movie's release) marking the 20th anniversary of the Simpsons franchise (when the Ullman Shorts are included).
During the skateboarding, the Multi-eyed squirrel jumps onto Bart's shoulder and tries to bite him but gets shoved off by one of "Burns Construction"'s wrecking balls.
Bart skateboards through a broken and damaged Springfield, currently under repair.
Shards of the destroyed dome and characters from the movie are visible as Bart skateboards through the streets.
When Homer pulls into the driveway, the "Pig Crap" silo is strapped to the roof of his car.