In a small bowl, combine the smoked paprika, Italian seasoning, salt, and black pepper. Pat the chicken chunks dry with paper towels, then toss them with the spice mixture until evenly coated. Heat 2 tablespoons of olive oil in a large skillet over medium-high heat until shimmering. Working in batches if needed to avoid crowding, sear the chicken for 3 minutes per side until golden brown (the chicken won't be fully cooked yet, which is fine). Transfer the seared chicken to a clean plate and set aside.

In the same skillet, add 1 tablespoon of olive oil and the orzo. Toast the orzo for 2 minutes, stirring constantly, until it becomes fragrant and lightly golden—this step adds a subtle nutty flavor. Add the minced garlic and stir for about 30 seconds until fragrant. I've found that toasting orzo before adding liquid gives it much better texture and prevents it from becoming mushy.

Pour in the chicken stock and add half of the halved cherry tomatoes along with 1/2 teaspoon of salt. Bring the mixture to a boil, then reduce heat to medium and simmer for 5-10 minutes, stirring occasionally, until the orzo is tender and most of the liquid is absorbed but the mixture still has a slight sauciness. The orzo should have a creamy consistency naturally from its starches releasing into the liquid.

Stir the spinach into the orzo mixture along with the remaining halved cherry tomatoes. Continue stirring for 1-2 minutes until the spinach is fully wilted and the tomatoes have warmed through. The residual heat will be enough to cook the spinach without losing its bright color.

Reduce the heat to low and stir in the heavy cream and basil pesto until fully incorporated and the sauce is smooth and velvety. The pesto adds incredible herbaceous depth—I've noticed this really transforms the dish from simple comfort food to something more restaurant-quality. Let it warm through for about 1 minute, stirring gently.

Return the seared chicken from Step 1 to the skillet and gently fold it into the creamy orzo mixture. Simmer everything together on low heat for 2-3 minutes, stirring gently, until the chicken is heated through and all flavors are melded. The chicken will finish cooking in the residual heat of the sauce. Taste and adjust seasoning if needed before serving warm.