Caribbean Elaenia
Elaenia martinica
The Caribbean elaenia is 14 to 18 cm (5.5 to 7.1 in) long and weighs 18 to 29 g (0.63 to 1.0 oz). It is largish elaenia and has a bushy crest. The sexes have the same plumage. Adults of the nominate subspecies E. m. martinica have a dull olive to brownish olive crown with a white stripe in the middle of the crest. They have whitish lores and a faint whitish eyering on an otherwise mottled gray-brown face. Their upperparts are dull olive to brownish olive. Their wings are dusky with yellowish to whitish edges on the flight feathers and tips on the coverts; the latter show as two wing bars. Voice: The Caribbean elaenia's song is a "drawn-out pee-wee-reereeree". Its call is a repeated "jui-up, wit-churr".
ID text from Wikipedia, CC BY-SA 4.0
Mountain Elaenia
Elaenia frantzii
The mountain elaenia is 14 to 15 cm (5.5 to 5.9 in) long and weighs about 14 to 24 g (0.49 to 0.85 oz). It is a small to medium size elaenia with a rounded crest. The sexes have the same plumage. Adults of the nominate subspecies have a brownish olive head with lighter cheeks, a thin very pale olive eyering, and a mostly hidden white patch on the crown. Their upperparts are grayish olive. Their wings are mostly dusky with pale olive or olive-yellow edges on the flight feathers. The tips of their wing coverts are yellowish olive and show as two bars on the closed wing. Voice: The northern and southern pairs of subspecies of the mountain elaenia have somewhat different vocalizations, which is part of the evidence hinting that they are separate species. The dawn song of the northern pair is "an endless repetition of an overslurred whistle followed by a rising burry part and a higher-pitched second overslurred note, all three notes interconnected without a clear pause".
ID text from Wikipedia, CC BY-SA 4.0

Where you might meet both
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Play today's Daily BirdPhotos and recordings are credited to their authors under the licence shown. Full profiles: Caribbean Elaenia and Mountain Elaenia.