drake chicago freestyle

Drake – Chicago Freestyle Ft. Giveon | Lyrics Meaning & Song Review

Drake surprised the fans with a double release titled “When to Say When” and “Chicago Freestyle” as the March 2020 began. Both tracks are played back-to-back, complete with a music video. In this article, we will take a look at the “Chicago Freestyle” part of the release.

On February 8, 2020, Drake was seen shooting a music video in Brooklyn, which suggested that new music was on the way.

“Chicago Freestyle” samples Eminem’s 2002 release “Superman” on the hook. The lyrics have been slightly modified by Drake. We know there is no beef between the two now!

Watch “When to Say When” & “Chicago Freestyle” Music Video by Drake

Lyrics Review and Song Meaning of “Chicago Freestyle”


The California-based singer Giveon performs the soothing chorus of the track. In these lyrics, he shouts out to the city of Chicago, in line with the title of the song. He does so by talking to his crush to visit the iconic ‘The Bean’ monument in Chicago. He also calls the city from its historic unofficial name the ‘windy city.’ The city enjoys (or suffers) a cold breeze thanks to the Lake Michigan adjoining the city.

Verse 1

Drake starts off by talking about how busy his life has got after breaking into the mainstream arena in music. From tour bus to the plane and then again to the bus. He leaves the concerts through underground garages for his own safety but stays in the presidential suites at the hotels. In his free time, he hits the clubs with his mates.

Once in a while, he goes through his mobile just to see whom he still has on his contact list from his past. He tries to call up two ladies he “knew” in the past. One has a man now and the other number doesn’t connect. He recalls nights with them back in 2017. Losing the battle in his contact list, he just looks around for a kill. He might find one quite easily and he might blow a few thousand dollars in one night for her. But will she ever stay with him?


Drake performs the infamous hook from Eminem’s 2002 hit “Superman.” Just like the year 2000’s the song’s message is still relevant. The lyrics suggest that women come and go in his life, but it is not like he can give up. He will keep trying, drunk, hitting on the models that walk the runway!

Verse 2

Drake seems to address how people are thirsty for the spotlight that they even succumb to killing the competition. Drake, as one of the biggest artists in the world, must be scared to take a walk alone in the streets. In this specific situation, Drake draws a picture of a dinner, with a/the girl. The waiter brings the cheque and her eyes drop out thinking there is a mistake. So the guess of a couple of thousand dollars per meal seems to be right! But Drake’s got it covered.

Drake remembers when his American Express (AMEX) credit card had a limit on it. Being in the stature and wealth of Drake, he would obviously have ‘unlimited’ credit cards with him. But it was no easy task getting there. From tour truck to stage to shower to truck to stage was his mantra in the past. This also earned him plenty of women in the past and he admits to plenty of sinning in the past as well. So he seems to be taking a different approach now. Maybe slow down on the high-stakes life for a bit! In either case, Drake seems to suggest to us that the lifestyle of a superstar is not that freeing as we often tend to believe.

It is up to you to decide if this is the life you want to lead as a superstar or lead a free life as a normal person. Let us hear your thoughts on the song and the music video in the comments below.

Check out the complete lyrics and further song meaning breakdown on Genius.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.