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Google Flights can do that, see for example this search for flights from Mysłowice to Åre which found the small regional airports of Katowice and Östersund, click on "Change flight" in the flight details to see the original search query which only mentioned the places of departure and arrival, without any airports specified:
https://www.google.com/travel/flights/s/YqdhwS3UoZT9w3F17
Sadly it wouldn't let me put in multiple. And when I put in the town, it only had the nearest small airport, then all the far away major ones. I know of one other minor airport for sure and it wasn't even on the list.
Google Flights can do multiple stops too, see my example search here amended with an additional stop in Göttingen:
https://www.google.com/travel/flights/s/bXcwvQvRZU8i8PX87
As for why it doesn't find the particular airport you're looking for, that's impossible to guess without knowing which airport that is.