1917 or earlier: Cheechako = Chicago!
Apparently I’ve yet to write about this folk-etymology of a Chinook Jargon phrase…

Defending a dancehall girl in a knife fight while dogsledding? Just another day in Alaska
(image credit: The Western & Frontier Fiction Magazine Index)
Take it from me, as someone born in Alaska, the word cheechako is well-known in Alaskan English.
It’s obviously from Chinuk Wawa words (chxí cháku, ‘just came here’).
Possibly it’s a re-pidginization of CW by gold seekers in the Klondike era of the late 1890’s. This contact language has an unusual history of transitioning back & forth between being a second language for people (pidgin) and being a creole first language of entire communities.
But another idea that has had some popularity in Alaska for decades, which I’ve not yet written about here, is that cheechako = ‘Chicago’.
Some sources elaborate on this claim, asserting that, oh, it’s how “Eskimos” pronounce that city’s name, as if Inuit habitually discuss how it’s a helluva town…
All of this is factually wrong. The etymology part, I mean.
But as an, um, alternative fact, it’s taken root. Probably more folks in AK could now tell you the Chicago theory than can name Chinook Jargon.
Here’s a representative sample of what I’m talking about, from 1917:

COAST PAPER IS UNDULY EXCITED
(Valdez Miner)The bizarre crestions of Mr. Foster’s fancy may have existed
in Alaska in the early sixties, but nowadays the population of
Alaska is drawn from every part of the United States, and we
might say of the world. In New York itself the citizens cannot
be more cosmopolitan. The author can find thousands of men in
the hil’s more familiar with New York than he himself, and the
New Yorker may rub shoulders with the man from Boston or the
cheechako from Chicago. The whole fabrication of misstatements
from Mr. Foster’s erticle seem to emanate from the fact that when
our people find a traveler who is easily gulled and hunting for the
unusual they give it to him, and the more he swallows the more
they supply to him, until he is stuffed to repletion with the fig-
ments of fancy his fertile imagination pictured before his arrival in
the territory. He is regaled with the stories he wants, while his
sources of information laugh at him for his gullibility. So far as
his story goes it is worthless, except as a wild, weird concoction of
something that has never existed only in the fancy of the untrav-
eled cheechako from the extreme East. It is appalling to consider
the ignorance of the customs and conditions of Alaska throughout
the States, and it seems to have run to seed in New York.
— from the Iditarod (AK) Iditarod Pioneer of March 17, 1917, page 2, column 2
I haven’t yet found occurrences of the cheechako = Chicago idea before 1917.
In fact, I’m inclined to suspect that cheechako‘s popularity in Alaskan English has more to do with a source that kinda goes against modern Alaska’s self-image:
Literature.
I really have to remind you folks that in the Klondike era, the poetry of Robert “Ballads of a Cheechako” Service and the stories of Jack “Call of the Wild” London were immensely popular — both in Alaska and “Outside”, as we call it.
People absolutely ate up both guys’ romanticization of life in The North. When you look through newspapers of that time, for instance, you’ll find countless references to, and quotations of, both authors. London’s stories were often serialized, running in installments in Outside papers.
Both fellas bandied the word cheechako (along with other Chinookisms) around like it was going out of style, a fate that both ensured wasn’t about to happen.
