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Chicken Spiedie Skewers with Italian Dressing

['1 garlic clove, finely grated', '5 tablespoons white wine vinegar', '2 tablespoons chopped Peppadew peppers in brine', '1 tablespoon mayonnaise', '1 tablespoon sugar', '1 1/2 teaspoons dried oregano', '1/2 cup olive oil, plus more', 'Kosher salt, freshly ground pepper', '1 1/2 pounds skinless, boneless chicken thighs (about 6)', '1 large sweet onion, sliced 1/2 inch thick', '2 beefsteak tomatoes (about 1 pound), sliced 1/4 inch thick', 'Oregano leaves and lemon wedges (for serving)', 'Six to nine 8-inch metal skewers', 'or wooden skewers soaked 30 minutes in water']

Whisk garlic, vinegar, peppers, mayonnaise, sugar, dried oregano, and 1/2 cup oil in a medium bowl; season with salt and pepper. Transfer half of dressing to a small bowl; cover and chill until ready to serve.
Cut chicken thighs lengthwise into long strips, about 1"–1 1/2" wide (you should get 2–3 pieces per thigh). Combine chicken and remaining dressing in a large resealable plastic bag. Seal bag, pressing out any air. Turn to coat and chill at least 20 minutes and up to 1 day.
Prepare a grill for medium-high heat; oil grate. Remove chicken from dressing; discard dressing. Thread 2 pieces of chicken onto each skewer. Season chicken lightly with salt and grill, turning occasionally, until golden brown and cooked through, 8–10 minutes.
Meanwhile, drizzle onion with oil; season with salt. Grill until browned on both sides but still firm in center, about 3 minutes per side. Transfer to a large bowl and add tomatoes and a couple splashes of reserved dressing. Toss to coat; season salad with salt and pepper. Top salad and chicken with oregano leaves.
Serve chicken with salad, reserved dressing, and lemon wedges for squeezing over.

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