Chicago Freestyle
Drake Lyrics


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Two thirty baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is, whenever I visit
Windy city, she blowing me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?
Ayy, truck to the plane, to the truck
Truck to the hotel lobby
Me, I go through underground garages
Presidential suite, on deposit
Elevator up to the room
Shower up and then we hit the club
Touchdown, gotta see what's up
Area code in my phone
What numbers do I still have?
Who do I know from the past?
Hit one, she say she got a man
Hit another one, it goes green
Must've changed phones on the team
'Member when you lead me in between?
That was 2017
All good, Chubbs'll look around
Find one that seem my type
That my dawg and he know what I like
He done found me plenty in my life
Problem is, I meet a girl tonight
Then I go and treat her too nice
Galleria credit card swipes
I don't even know if she a wife

But I do know one thing though
Women they come they go
Saturday, through Sunday, Monday
Monday through Sunday, yo
Maybe I'll love you one day
Maybe we'll someday grow
'Til then I'll sit my drunk ass on that runway
On this one way

Two thirty baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is, whenever I visit
Windy city, she blowing me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

Jewelry in the safe on arrival
Pistol on J for survival
Lot of people gunning for the title
Lot of people trying to take us viral
I'm just trying to have a nice night, though
Waiter brought the check for the meal
She said, "babe, I think there was a typo"
Nah girl, I got it, that's light though
I could show you bigger things than that
It's gon' be a minute 'til I'm back
Let me give you images that last
AMEX had a limit in the past
I had plenty women in the past
I done plenty sinnin' in the past
You don't need to know, but you can ask
Stickin' on your backstage pass
All access 'cause you bad
You could go wherever with that ass
Show, to the shower, to the truck
Truck, to the club, for the party
You go in first with your girls
'Cause I don't know who's out there watching

But I do know one thing though
Women they come they go
Saturday, through Sunday, Monday
Monday, Sunday, yo
Maybe I'll love you one day
Maybe we'll someday grow
'Til then I'll sit my drunk ass on that runway
On this one way

Two thirty baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is, whenever I visit
Windy city, she blowing me kisses, no
Thirty degrees, way too cold, so hold me tight




Will I see you at the show tonight?
Will I see you at the show tonight?

Overall Meaning

In "Chicago Freestyle," Drake reflects on a past relationship in which he had fun with a woman during his trip to Chicago. He invites her to meet him at The Bean (Cloud Gate sculpture) at 2:30 in the morning, but it's too early for her. He asks if he will see her at the show later that night. He proceeds to detail his lavish lifestyle and the problematic nature of his relationships with women that come and go. Despite his material wealth and access to women, Drake still finds himself alone and drunk.


The lyrics open with Drake using the iconic Cloud Gate sculpture to serve as a backdrop for a rendezvous with a lover in the Windy City. The Bean is a well-known public sculpture by British artist Anish Kapoor located in downtown Millennium Park in Chicago. The song also highlights various places as Drake travels from the airport to his presidential suite with underground garages, showers, resort lobbies, clubs, and backstage passes. The rapper admits to having had plenty of women and sinning in the past, hinting at his promiscuous lifestyle, although he admits he cannot remember all their phone numbers. Drake uses his signature rhyme scheme to highlight how fleeting women can be but also grapple with the idea that maybe he will one day find true love.


Line by Line Meaning

Two thirty baby, won't you meet me by The Bean?
Let's meet at The Bean in Chicago later today.


Too early, maybe later you can show me things
It might be too early to explore the city, but perhaps later you can show me around.


You know what it is, whenever I visit
Every time I come to Chicago, you know what to expect.


Windy city, she blowing me kisses, no
Chicago is known as the Windy City, but it seems like the girl is giving me kisses instead.


Thirty degrees, way too cold, so hold me tight
It's too cold outside, so please hold me close to keep me warm.


Will I see you at the show tonight?
Are you coming to see me perform tonight at the show?


Ayy, truck to the plane, to the truck
I'm traveling by truck to the airport, and then by plane to my destination.


Truck to the hotel lobby
From the airport, I take a truck to the hotel lobby.


Me, I go through underground garages
I prefer to use underground garages to travel incognito.


Presidential suite, on deposit
I've reserved the presidential suite and put down a deposit for it.


Elevator up to the room
I take the elevator up to my room.


Shower up and then we hit the club
After freshening up, we're going to go party at the club.


Touchdown, gotta see what's up
After touchdown, I need to figure out what's going on.


Area code in my phone
I have many different area codes in my phone from across the country.


What numbers do I still have?
I'm not sure which numbers I still have saved in my phone.


Who do I know from the past?
I'm trying to remember who I might know from my past travels.


Hit one, she say she got a man
I text one of my contacts, but she tells me she has a boyfriend.


Hit another one, it goes green
I text another contact, and they respond positively.


Must've changed phones on the team
I might have changed phones since I last spoke with some people on my team.


'Member when you lead me in between?
Remember when you led me through the city last time?


That was 2017
That happened back in 2017.


All good, Chubbs'll look around
It's all good, my friend Chubbs will help me find someone.


Find one that seem my type
He's going to find someone who matches my preferences.


That my dawg and he know what I like
Chubbs is my friend, and he knows what kind of women I'm into.


He done found me plenty in my life
Chubbs has helped me find many women in my life.


Problem is, I meet a girl tonight
The problem is that I might meet a girl tonight and be too nice to her.


Then I go and treat her too nice
I tend to be too kind to the women I meet.


Galleria credit card swipes
I often spend a lot of money on shopping sprees, and swipe my credit card at places like Galleria.


I don't even know if she a wife
I can't even tell if the woman I'm with is someone I'd want to marry.


But I do know one thing though
The one thing I know for sure is that...


Women they come they go
Women come and go in life.


Saturday, through Sunday, Monday
From Saturday to Monday and every day in between.


Maybe I'll love you one day
Perhaps I'll love someone one day.


Maybe we'll someday grow
Maybe we'll both grow and mature together.


'Til then I'll sit my drunk ass on that runway
Until then, I'll just sit here at the airport, drunk and waiting.


On this one way
With no return ticket.


Jewelry in the safe on arrival
I keep my valuable jewelry locked up safely when I arrive at my destination.


Pistol on J for survival
I carry a gun for protection and survival, and my friend J is with me.


Lot of people gunning for the title
Many people are trying to take my title, but I'm not concerned.


Lot of people trying to take us viral
Many people are trying to get famous by associating themselves with me and my crew.


I'm just trying to have a nice night, though
Despite all the attention and drama, I just want to have a fun night.


Waiter brought the check for the meal
The waiter brings the check for our meal at the restaurant.


She said, "babe, I think there was a typo"
My date thinks there was a mistake on the bill.


Nah girl, I got it, that's light though
I assure her that the bill is not a problem and it's not too expensive.


I could show you bigger things than that
I can afford to show her more extravagant things if I wanted to.


It's gon' be a minute 'til I'm back
It might be a while before I come back to this city.


Let me give you images that last
Let me create lasting memories for you before I leave.


AMEX had a limit in the past
In the past, my American Express card had a limit on how much I could spend.


I had plenty women in the past
I've had many women in my past.


I done plenty sinnin' in the past
I've done many sinful and regrettable things in my past.


You don't need to know, but you can ask
I'm not obligated to share my past with anyone, but they can still inquire.


Stickin' on your backstage pass
I give her a backstage pass as a memento of this night.


All access 'cause you bad
She gets all access because she's attractive and special.


You could go wherever with that ass
She can go anywhere and do whatever she wants because she's with me.


Show, to the shower, to the truck
From the show to the shower to the truck, our night continues.


Truck, to the club, for the party
We continue on from the truck to the club for the party.


You go in first with your girls
She enters the club first with her friends for safety reasons.


'Cause I don't know who's out there watching
Because I don't know who might be watching us from the crowd.




Lyrics © Universal Music Publishing Group, Sony/ATV Music Publishing LLC, Kobalt Music Publishing Ltd.
Written by: Aubrey Graham, Giveon Evans, Rupert Thomas

Lyrics Licensed & Provided by LyricFind
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Most interesting comment from YouTube:

@33Oak

[Chorus: Giveon]
Two-thirty, baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is whenever I visit
Windy city, she blowin' me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

[Verse 1: Drake]
Ayy, truck to the plane to the truck
Truck to the hotel lobby
Me, I go through underground garages
Presidential suite on deposit
Elevator up to the room
Shower up and then we hit the club
Touch down, gotta see what's up
Area code in my phone
What numbers do I still have?
Who do I know from the past?
Hit one, she say she got a man
Hit another one, it goes green
Must've changed phones on the team
'Member when you let me in between
That was 2017
All good, Chubbs will look around
Find one that seem my type
That my dawg and he know what I like
He done found me plenty in my life
Problem is, I meet a girl tonight
Then I go and treat her too nice
Galleria credit card swipes
I don't even know if she a wife

[Pre-Chorus: Drake]
But I do know one thing though
Women, they come they go
Saturday through Sunday, Monday
Monday through Sunday, yo
Maybe I'll love you one day
Maybe we'll someday grow
'Til then, I'll sit my drunk ass on that runway
On this one way

[Chorus: Giveon]
Two-thirty, baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is whenever I visit
Windy city, she blowin' me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

[Verse 2: Drake]
Jewelry in the safe on arrival
Pistol on J for survival
Lot of people gunnin' for the title
Lot of people tryna take us viral
I'm just tryin' to have a nice night though
Waiter brought the check for the meal
She said, "Babe, I think there was a typo"
Nah, girl, I got it, that's light though
I could show you bigger things than that
It's gon' be a minute 'til I'm back
Let me give you images that last
AMEX had a limit in the past
I had plenty women in the past
I done plenty sinnin' in the past
You don't need to know, but you can ask
Stickin' on your backstage pass
All access 'cause you bad
You could go wherever with that ass
Show to the shower to the truck
Truck to the club for the party
You go in first with your girls
'Cause I don't know who's out there watchin'

[Pre-Chorus: Drake]
But I do know one thing though
Women, they come they go
Saturday through Sunday, Monday
Monday, Sunday, yo
Maybe I'll love you one day
Maybe we'll someday grow
'Til then, I'll sit my drunk ass on that runway
On this one way

[Chorus: Giveon]
Two-thirty, baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is whenever I visit
Windy city, she blowin' me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?



All comments from YouTube:

@fpn925

Unpopular Opinion: One of Drake’s best ever songs

@AustinCMN

The best part of the verses was from Em though.

@maxhitikos

AustinCMN yeah, that’s called homage bro

@jdottdeestv8149

@@maxhitikos A very nice nod indeed, can't lie it had me popping when i first herd this tune and this tune is most definitely one of ~Drake top 'vibe to tune'

@AustinCMN

@@maxhitikos i know it's homage but still... i personally think it's one of the best parts of the song and you can't really credit Drake for that

@picarso7630

Ehh nah

541 More Replies...

@alexalvarez7704

This song hits different on a drive at night

@jessedobson1009

It literally just dropped. You didnt even have time to grab your keys.. 😐

@alexrealg1511

I think most drake songs are nice at night

@jacobday3087

Jesse Dobson bruh it’s been out for a minute, just as two songs in one YouTube video

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