Treat this as a starting point rather than a closed room. Curiosity about Jamaica usually comes with curiosity about the Caribbean more broadly, and Saint Kitts and Nevis or Barbados are never more than a skip away once you get going.
Conversations from Jamaica run in English from the first line. That makes it an easy place to start if you are new to random chat and would rather not negotiate a language barrier at the same time.
Clocks in Jamaica run on UTC−5. Their evening — call it 10pm local — is 7pm in Los Angeles and 3am in London, which is worth a glance if you would rather catch people while they are relaxed than while they are getting ready for work.
Entirely free. OmegleLite runs on donations rather than subscriptions, so nobody in Jamaica — or anywhere else in the Caribbean — is asked for a card, a sign-up fee or an ad break before reaching the queue.
You stay anonymous. OmegleLite asks visitors from Jamaica for no email, no social login and no personal details — only confirmation that you are over 18, whether you arrive at 10pm local or mid-afternoon.
You will not need a translation tab for Jamaica — English is spoken day to day. Slang and pace vary far more than vocabulary does, especially across the Caribbean.
Their evening is the window that works — 10pm at UTC−5. Convert it to your own clock (7pm in Los Angeles, 3am in London) and start your session so the two overlap.