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Slice chicken breasts into thinner strips. Generously season the chicken with smoked paprika, Italian seasoning, salt, and pepper.
Heat a large, high-sided, heavy-bottomed skillet over medium heat. Add 2 tablespoons of olive oil. Add chicken. Cook the chicken on medium heat for about 3 minutes per side. Remove chicken to a plate.
To the same, now empty, skillet, add 1 cup of uncooked orzo, 5 cloves of minced garlic, and 1 tablespoon of olive oil. Cook the orzo on medium heat, stirring, for about 2 minutes until browned.
Add 2 cups of chicken stock, half of the cherry tomatoes, and ¼ teaspoon of salt. Bring to a boil, then reduce to a simmer and cook for about 5 or 10 minutes, occasionally stirring to prevent the orzo from sticking to the bottom of the pan, until the orzo is cooked through.
Add spinach and the remaining cherry tomatoes. Stir everything on low-medium heat until the spinach wilts.
Add heavy cream and basil pesto to the skillet with orzo and veggies and stir to combine. Season with salt and pepper, if desired.
Return the chicken to the skillet. Allow the chicken to simmer in the sauce to heat through and until the chicken is completely cooked through.