Songfacts®:

• Over dreamy piano, Drake reflects on some romantic discontent during a tour stop in Chicago. After arriving in the Windy City, Dreezy tells us how he unsuccessfully tried to hook up with a couple of girls he knows.
  
  Hit one, she say she got a man
  Hit another one, it goes green
  Must've changed phones on the team
  
  Drake got a member of his OVO crew, Chubbs, to find him a new female, but the Toronto MC is starting to think this unidentified lady may only agree to spend the night with him because of his fame and wealth.
• Drake concludes that he is tired of such transient relationships, and is looking for someone he can settle down with.
  
  But I do know one thing though
  Women they come they go
  Saturday, through Sunday, Monday
  Monday through Sunday, yo
  
  The lyrics are an interpolation of some of Eminem's rhymes on his 2002 track, "Superman."
• Long Beach, California singer Giveon croons the hushed chorus. It is his first collaboration with Drake.
  
  Giveon is signed to Toronto record producer Sevn Thomas's record label Not So Fast, so it is likely the hook-up came about via Thomas.
• Drake released "Chicago Freestyle" simultaneously with "When to Say When" and the accompanying Theo Skudra-directed music video features both songs. Skudra is Drake's photographer and has shot several of his music clips, including the ones for "Nonstop," "Money in the Grave" and "War."