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shameless pleading


Steady there, cowboy.

Dear Word Detective:  “Chicago, Chicago … that toddlin’ town.”  What does “toddlin'” mean?  Do people “toddle” because they:  (a) imbibe excessively, (b) are buffeted by so much wind?  (It’s amusing that “Windy City” refers to blustering politicians) or (c) are wearing so much clothing to protect them from the weather that they toddle about, much like the little brother encased in a snowsuit who cannot put his arms down in “The Christmas Story”? — EC Goller.

Hey, I had a snowsuit like that.  But it didn’t bother me as much as the little halter-and-leash combo my parents made me wear when we went somewhere where there were crowds.  In retrospect, I understand why they did it.  I was a small, vague child, and easily misplaced.  But I do think the muzzle was overkill.

Onward.  You mention “Windy City” as the nickname of Chicago, which requires me to explain that the term was not, as is often said, coined by New York Sun editor Charles A. Dana during the 1890s tussle between New York and Chicago for the right to hold the 1893 Columbian Exposition (the World’s Fair held to celebrate the 400th anniversary of Columbus’s arrival in America).  Etymologist Barry Popik ( has found uses of “Windy City” in print as early as 1856, and it was frequently deployed in inter-city rivalry between Chicago and Cincinnati in the 1860s and 70s, in which “windy” had the dual meaning of “literally windy” and being “windy” with bombast and empty boasts.

The song “Chicago,” which begins “Chicago, Chicago, That toddling town, Chicago, Chicago, I’ll show you around,” was written in 1922 by Fred Fisher and has been recorded by numerous artists, the versions by Frank Sinatra and Tony Bennett being especially popular.

I would suggest a trip to Chicago to ask the natives what “toddling” in the song means, but they seem to have spent the past ninety-plus years trying, with no success, to figure that out.  The verb “to toddle” dates back to around 1600 and initially, as defined by the Oxford English Dictionary, meant “to walk or run with short unsteady steps, as a child just beginning to walk [or] an aged or invalid person.”  That’s obviously the sense that gave us “toddler” meaning “a very young child.”  By the early 18th century, however, “toddle” was also being used to mean “to walk in a leisurely fashion, to stroll.”  The roots of “toddle,” incidentally, are unknown, but it may be related to “totter,” which would fit well with that first meaning.

As to whether “toddling” in the song refers to walking with difficulty (presumably because of inebriation, though wind might be a contributing factor), or to strolling along in a leisurely fashion, perhaps on the shore of Lake Michigan, both possibilities are arguable.  But I’m afraid that the most likely answer is “neither.”  “Toddling town” was probably picked simply because it’s nicely alliterative, always a good idea for the first line of nearly anything.  Having begun his song with “Chicago, Chicago” and wanting to follow up with “That T-something-something Town,” Fred Fisher’s choices were, after all, limited.  “Tootling”?  Too creepy. “Truculent”?  Bad for business.  “Terrific”?  Too needy, and it doesn’t scan properly.  “Tedious”?  Only if he longed for cement overshoes.  All things considered, “toddling” seems almost inevitable.

8 comments to Toddling

  • I always assumed the lyric “toddlin'” in “Chicago, Chicago” published by Fred Fisher in 1922 was used to infer the term strut, a pompous, self-important gait, meaning Chicago was “It” in the Clara Bow-Elinor Glyn, Roaring 20s sense of the word. The Darktown Strutters Ball and Stomping At The Savoy also come to mind as describing happening, lively places full of action and movement, rather than being quiet, dull or sedate.

  • Denise Rose

    Wasnt “The Toddle” a dance of the 20s ? I thought that’s what the word means in the song lyric !

  • scott anderson

    I was also curious about the origins of “that toddlin’ town”; came across your website, but still no luck. Then I recalled hearing somewhere that the “toodle-oo” in “East St. Louis Toodle-oo” was once pronounced something more like, “toddle -o”. I found this site/page:
    It seems to shed some more light if you don’t mind wading through the scholarly verbiage. Looks like ” toddlin’ “could be a sensual dance/tottering walk/approach to life.

  • Ben

    Just a thought, but as America’s “Second City,” it’s not inconcievable that Fisher imagined Chicago “toddling along” in the shadow of its “fully grown” counterpart in New York.

    • rob

      Second city refers to the chicago fire which resulted in most of chicago being rebuilt – today’s chicago is the second city.
      Not New Yorks little brother.

  • Doug

    Denise is correct. The Toddle was a style of dancing used with the jazz music of the 20’s when this song was written. It was popular in Chicago, and a variation of the style was even called “the Chicago.” The song is about Chicago’s jazz-oriented night life during the flapper era. “You’ll lose the blues” and have the time of your life — maybe even dance with your wife!

  • Pete Lacaba

    This dance website says that the toddle was a dance that had “a smack of jazz” and was “an offshoot of the foxtrot”:

  • PJB

    Concur with the people who say it was the dance, “the Toddle.” Chicago appears to have been the center of “Toddling.”

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