Heat a deep skillet or Dutch oven with a tight-fitting lid over medium-high heat. Add 1 tablespoon oil.
Once the oil is hot, add in the chicken, 1 teaspoon Italian seasoning, 1 teaspoon paprika, and 1/2 teaspoon salt. Saute, stirring occasionally, until the chicken is golden on all sides and cooked through, 4 to 6 minutes. Remove to a plate.
Reduce the heat to low. Add 1 tablespoon oil and the shallot. Cook, stirring often, until the shallot is softened, about 3 minutes. Add the garlic, black pepper, and the remaining 1 teaspoon Italian seasoning, 1 teaspoon paprika, and 3/4 teaspoon kosher salt. Cook and stir for 30 seconds, until the garlic is fragrant.
Stir in the orzo and tomato. Cook 1 minute, stirring constantly, to coating the orzo with the oil and spices and toast it slightly.
Stir in the broth. Increase the heat to bring it to a gentle boil, stirring very frequently with a wooden spoon and scraping the spoon along the bottom of the pot to prevent the orzo from sticking. Cover the pot and reduce the heat to medium. Cook the orzo, lifting the lid occasionally to stir and run the spoon along the bottom to prevent sticking, until most of the liquid is absorbed and the orzo is al dente, 12 to 14 minutes. During the last several minutes, scrape along the bottom very frequently.
When the lid is on, you should hear the water boiling steadily underneath it (but you don’t want it boiling so hard, you start to wonder if the lid is going to lift off). If the orzo looks dry at any point, add several splashes of broth as needed to loosen it.
Stir in the Parmesan, then the spinach, red pepper flakes, half of the basil, and the reserved chicken. Continue stirring until the spinach has just wilted, about 1 minute. Taste and season with additional salt, pepper, and red pepper flakes as desired (I add another pinch or two of salt; the amount you need will vary based on your chicken broth). Serve hot, sprinkled with remaining basil and additional Parmesan.
