Make the population of Chicago surpass new york

What has to happen for the populationof Chicago to surpass the population of New York sometime during the latter half of the 20th century?
 
What has to happen for the populationof Chicago to surpass the population of New York sometime during the latter half of the 20th century?

Prevent the consolidation of NYC and have Chicago become the center of the automobile industry. Later on, perhaps have Chicago become a tech capital as well as a result of its connections to the Manhattan Project?
 
Pierpont Morgan gets sick of NYC for some reason and in a hissy fit moves himself and ALL of his financial entities to Chicago. Wall Street relocates en masse to LaSalle Street and the Chicago Stock Exchange puts the NYSE in it shadow. Now that Morgan is in Chicago his finance draws Ford and the other early auto entrepreneurs there. When Chicago expanded to annex the surrounding townships in the 1890's they annex at least one level of townships more in all directions while avoiding the already established railroad suburbs. It is especially important to annex aggressively to the south, where the Auto plants will grow like a Ford planted and Morgan watered bonanza from the former cornfields. And while Chicago is expanding NYC does not incorporate Brooklyn and friends. Follow the money friends, follow the money.
 
A more destructive great fire in 1871 results in a even bigger 'grand rebuilding plan' and this gives the City (a place I visited last year and was very impressed) greater scope for well organised and planned growth with our ATL Chicago city planned from the 1870s to reach as deep in land from the lake as far East as the Fox river.

Building escalates during the 1890s as more modern building techniques allow for Steel Skeleton 'Sky Scrapers' the worlds first examples of these buildings

Also the public Pillorying of Mrs O'Leary who had been blamed for the fire does a 180 and backfires on those attempting to vilify the Irish-American community and instead Chicago by 1880 becomes a haven for Irish Immigrants (competing with places like New York) and experiences a faster population explosion

Later as the city grows the more recognisable German, Swedish, Polish etc join the Irish in making up the majority of the City's rapidly growing population

I cannot see New York not growing like it did but given an improved plan post the 1871 Fire I can see the 'Smelly Flower' becoming grander than it is today
 
Most of the ground work for NYC's 20th C expansion was pre-1900, so a pre-1900 POD would be your best bet. Kill off the Erie Canal and you keep Baltimore and Philly in the running. And the growth of NYC is more distributed.
 
re CryHavoc, Well-organized and planned growth have never been in Chicago's DNA. Even after a "Greater Fire" rebuilding would have been immediate and haphazard as it was after the "Great Fire". Very little of the only real grand plan for Chicago, Burnham's on 1908, was really adopted. And no matter how 'welcoming' Chicago is to immigrants, the physical fact remains that in the steamship age immigrants are going to arrive on the East Coast first and many will stay there. So a Greater Fire might result in a stinkier flower, but not to the size of OTL New York.
 

missouribob

Banned
After a limited nuclear war in which Washington D.C. and New York City are destroyed (maybe a Anglo-Nazi War that ends with nuclear weapons?) Chicago becomes the financial capital of the United States (and the world) and St Louis the political capital.
 
re CryHavoc, Well-organized and planned growth have never been in Chicago's DNA. Even after a "Greater Fire" rebuilding would have been immediate and haphazard as it was after the "Great Fire". Very little of the only real grand plan for Chicago, Burnham's on 1908, was really adopted. And no matter how 'welcoming' Chicago is to immigrants, the physical fact remains that in the steamship age immigrants are going to arrive on the East Coast first and many will stay there. So a Greater Fire might result in a stinkier flower, but not to the size of OTL New York.

Well I tried
 
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