The Second City native, wearing a red Chicago's Teacher Union sweatshirt, opened his monologue by noting that he gave $1 million to Chicago's public schools in 2017, the same year he first hosted the NBC late-night comedy show.
"I'm happy to say it completely fixed everything," he noted dryly.
As a sign that his contribution hasn't solved all the school system's problems, he acknowledged Chicago's teachers, who are on strike. "I fully support you."
Chance, a solid sketch performer who also was the evening's musical guest, then turned his focus to honoring Chicago and its nickname, the Second City, with a snappy tune dedicated to No. 2's, because, as he rapped, "Sometimes the second best is better than the first."
The song went on to recite his favorites – Bing over Google; Burger King's French fries over McDonald's; Pepsi over Coke; Adam Carolla over Jimmy Kimmel, and so on – as cast members Heidi Gardner and Melissa Villaseñor flipped picture cards detailing each example.
Previously on 'SNL': Chance the Rapper brings the musical comedy as first-time host
Chance was doing fine until cast member Kyle Mooney horned in on the act with a not-so-convincing explanation that he's from San Diego, "the second city of Southern California."
Chance wasn't buying it, but that didn't stop Mooney, who joined in on the rap. They teamed on more No. 2's that should be No. 1: "Antz" over "A Bug's Life," Redbox over Netflix and Scrappy over Scooby-Doo, along with a joint tribute to the Los Angeles Clippers, Brooklyn Nets and Chicago White Sox – a duet that will especially delight list makers.
Mooney stopped the song with this rhyme: "I like Hanukkahs more than Christmases/I don't like islands but I love isthmuses."
"What's an isthmus?" Chance asked.
"It's a narrow strip of land connecting two bigger pieces of land," Mooney explained correctly.
"And that's the second best to islands?" an unconvinced Chance asked.
"For the purposes of this song, yes," Mooney said.
They added a few more – The Coffee Bean & Tea Leaf over Starbucks, "Angel" over "Buffy the Vampire Slayer" – before Chance, after dismissing Mooney's request to be on his next album, brought the song home with a rousing ending:
"Yeah, I'm the kind of guy that likes the second-best best/I think Chicago is better than the rest.
I take seconds at dinner/And second glances/I believe in second chances.
I love my wife and my family is true/A month ago we welcomed daughter No. 2.
Now, I'm in New York/It's great to be alive/I'm back for the second time hosting 'Saturday Night Live.'"
This article originally appeared on USA TODAY: 'SNL': Chance the Rapper song salutes Chicago and other second bests