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Cucumber and Charred Onion Salad

['1 Fresno chile, thinly sliced into rings, seeded if desired', '4 tablespoons red wine vinegar, divided', '2 medium red onions, sliced into 1/4" rounds', '4 tablespoons olive oil, divided, plus more for serving', 'Kosher salt, freshly ground pepper', '1 medium English hothouse cucumber, sliced into rounds', '1/4 teaspoon dried oregano']

Prepare grill for medium-high heat. Combine chile and 2 tablespoons vinegar in a small bowl; set aside.
Place onions on a rimmed baking sheet and drizzle with 2 tablespoons oil; season with salt and pepper. Turn to coat. Grill onions directly on grate until lightly charred and softened, about 2 minutes per side. Transfer to a large bowl and toss with remaining 2 tablespoons vinegar; let cool.
Coarsely chop 1/2 cup grilled onion and return to bowl. Add chile and soaking liquid, cucumber, dried oregano, and 2 tablespoons oil and toss to combine; season with salt and pepper. Serve drizzled with more oil.

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