Chicago
Frank Sinatra With Billy May And His Orchestra Lyrics


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I got the surprise, the surprise of my life
I had to stop and stare
I saw a man dancing with his own wife
And you'll never guess where

Chicago, Chicago--that toddlin' town, that toddlin' town
Chicago, Chicago--I'll show you around; I love it
Betcha bottom dollar you'll lose your blues
In Chicago, Chicago--the town that Billy Sunday could not shut down

On State Street, that great street
I just want to stay, I just want to stay
They do things they don't do on Broadway, say
They have the time, the time of their life

I saw a man who danced with his wife
In Chicago, Chicago, Chicago, Chicago
Free and easy town, brassy, breezy town
Chicago, Chicago

Let me cool my heels right down at Marshall Field
Come and walk with me along the lake to the drake
Holler and hoot all through the loop
Shout out now to Mrs. O'Leary's cow

No she-she, life is peachy
Chicago--we'll meet at the Pump Room Ambassador East
To say the least
On shishkabob and breast of squab we will feed and get free

Don't tell me sin is ramped and right
Think of that man who danced with his wife




In Chicago, Chicago
I feel sympathy for that wonderful, windy town

Overall Meaning

The song "Chicago" by Frank Sinatra with Billy May and his Orchestra is a celebration of the diverse cultural aspects of the city of Chicago. It starts off with the singer expressing his surprise at witnessing a man dancing with his own wife, and goes on to describe how much he loves the city of Chicago, where he can lose his blues. According to the lyrics, the town is so brassy and breezy that "they do things they don't do on Broadway". The song also pays homage to some of Chicago's famous landmarks such as State Street, where people have the time of their lives, Marshall Field, and the Pump Room Ambassador East, where they feast on shishkabob and breast of squab.


The song is more than just a mere tribute to the city; it is a testament to the spirit of the people in Chicago. The singer expresses his admiration for the city's resilience, evident from the time of the Great Chicago Fire in 1871, and how they bounced back to rebuild the city. Even the notorious Mrs. O'Leary's cow, which was blamed for starting the fire, is celebrated in a shout-out in the song. Overall, the song is not just about the Chicago of the singer's time but celebrates the city's rich history and the diversity that still exists today.


Line by Line Meaning

I got the surprise, the surprise of my life
I received the greatest surprise of my existence


I had to stop and stare
I was taken aback and had to pause to observe


I saw a man dancing with his own wife
I witnessed a man flamboyantly dancing with his spouse


And you'll never guess where
It would be impossible for you to determine the location


Chicago, Chicago--that toddlin' town, that toddlin' town
Chicago, a bustling city with exciting entertainment


Chicago, Chicago--I'll show you around; I love it
I will introduce you to the lively town of Chicago, the city I fondly adore


Betcha bottom dollar you'll lose your blues
I promise you will forget your sadness


In Chicago, Chicago--the town that Billy Sunday could not shut down
In the town of Chicago, even Billy Sunday couldn't stop the excitement


On State Street, that great street
On the illustrious State Street


I just want to stay, I just want to stay
I have a strong desire to remain in this place


They do things they don't do on Broadway, say
They engage in activities that are not found on Broadway


They have the time, the time of their life
Everyone is having the most spectacular time


Let me cool my heels right down at Marshall Field
I am going to relax at Marshall Field


Come and walk with me along the lake to the drake
Join me for a walk by the lake to get to the Drake


Holler and hoot all through the loop
Yell and scream while crossing the loop


Shout out now to Mrs. O'Leary's cow
Pay homage to Mrs. O'Leary's cow


No she-she, life is peachy
Life is not pretentious, it's fantastic


Chicago--we'll meet at the Pump Room Ambassador East
In Chicago, let's arrange to meet at the Pump Room Ambassador East


To say the least
To understate the significance of the statement


On shishkabob and breast of squab we will feed and get free
We'll eat shishkabob and breast of squab and have the luxury of complimentary food


Don't tell me sin is ramped and right
Don't regale me with tales of excessive wrongdoing and incorrectness


Think of that man who danced with his wife
Consider the man who danced with his significant other


In Chicago, Chicago
In the city of Chicago


I feel sympathy for that wonderful, windy town
I have a profound empathy for the magnificent, blustery city




Lyrics © Sony/ATV Music Publishing LLC, Warner/Chappell Music, Inc., Universal Music Publishing Group, Songtrust Ave
Written by: JOHN BALDWIN GOURLEY

Lyrics Licensed & Provided by LyricFind
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