"Chicago Freestyle" is a song by Canadian rapper Drake and American singer-songwriter Giveon.

[2] The video stars Drake walking around New York City with scenes filmed in Marcy Projects in Brooklyn.

[4] Lyrically, Drake "unpacks the run-of-the-mill anxieties and flexes" associated with his nightlife, while portraying "an underrated antagonist", as described by a Pitchfork article.

"[6] Kevin Montes of Medium deemed the song "one of the original standouts with its subtle melancholy vibe to Drake's reflection of celebrity life in his verses.

"[7] In a mixed review of both "Chicago Freestyle" and "When To Say When", Sheldon Pearce of Pitchfork felt Drake "doesn't play the heel nearly as well as '02 Em used to.