“Chicago Freestyle” released simultaneously with Drizzy’s “When To Say When.” Drake dedicates his lyrics to the lessons he learned on his come-up and reflects on the various mistakes he made in his past relationships.
The song came about as Giveon was on tour with Snoh Aalegra and decided to make a freestyle for every city he visited, hence “Chicago Freestyle”. The title’s usage may or may not be a reference to Drake’s AM/PM series as a result, which contains similar elements. This would mark Drizzy’s first addition to the mini grouping since June 2016’s “4PM in Calabasas,” as he continues to revisit his past and focuses on lyricism. It is likely that Drizzy recorded the single in the “Windy City,” as his AM/PM series typically were named based on location.
The track was officially released to streaming services on May 1, 2020 as part of Dark Lane Demo Tapes.