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This sheet-pan dinner has it all: jammy roasted tomatoes, crispy chickpeas, warm and melty feta cheese, and minimal dirty dishes. Pita makes a great vessel for scooping up the flavorful mixture, but you could also pile it atop a bowl of quick-cooking bulgur, quinoa, or couscous, or eat it straight from the pan—we’ve been there.
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Place racks in middle and top positions of oven; preheat to 425°. Arrange 2 lb. heirloom or other large tomatoes, cored, cut into 1½"-thick wedges, on a rimmed baking sheet. Drizzle with extra-virgin olive oil and season generously with kosher salt and freshly ground pepper; toss to coat. Roast on middle rack until collapsed and slightly jammy, 25–30 minutes. Remove from oven and heat broiler.
Meanwhile, combine two 15.5-oz. cans chickpeas, rinsed, patted dry, 1 tsp. ground cumin, ½ tsp. smoked paprika, and 1½ tsp. Diamond Crystal or 1 tsp. Morton salt in a medium bowl. Drizzle lightly with oil and toss to coat.
Spoon chickpea mixture over and around tomatoes. Break 1 lb. feta, cut into ½"-thick slabs, into large pieces and tuck around. Broil on top rack until tomatoes and feta are blistered, 8–10 minutes. Let tomato-chickpea mixture cool 5 minutes.
Scatter 1 large handful arugula and ½ cup torn, pitted green olives over tomato-chickpea mixture. Drizzle some sherry vinegar or red wine vinegar and more oil over; season with pepper. Serve with pita.
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