I like this kind of thing.

For Portland I can sort of confirm almost everyone else in the world assumes Oregon too (though I also knew of Massachussetts Portland).

London is a fun one (London, Canada often comes up in this "thing" out in the wild).

Put in my hometown Aberdeen too, because until the past 2-3 years if you were literally searching from an IP address geolocated in Aberdeen, Scotland, then search results for Aberdeen would be full of random American stuff despite those being villages.

Quite fun to go through this list: https://en.wikipedia.org/wiki/List_of_the_most_common_U.S._place_names
Chester is a fun one, with 2 close and relatively insignificant so nearby it's a toss-up to either but farther afield enters probably/mainly for one or the other.