Dice the onion into 1/2-inch pieces and the carrot into 1/4-inch pieces, then mince the garlic. This prep work ensures everything is ready when you need it and prevents scrambling once cooking begins. Heat 2 tablespoons of olive oil in a large pot over medium heat. Once shimmering, add the diced onion and carrot, stirring occasionally for about 4-5 minutes until they begin to soften and the onion becomes translucent. This early cooking time allows the vegetables to release their natural sugars and develop a sweeter, more complex flavor base.

Add the minced garlic to the softened vegetables and cook for just 30 seconds until fragrant—this brief cooking time releases the garlic's flavor without allowing it to burn or become bitter. Sprinkle the flour over the vegetables and stir constantly for about 1-2 minutes to create a light roux that coats all the vegetables. This flour will act as a thickening agent and add body to the soup. Pour in the canned tomatoes (crushing them by hand as you add them if they're not already crushed) and stir well to combine everything thoroughly.

Pour in the chicken broth and add the dried oregano, stirring to combine. Increase the heat to medium-high and bring the soup to a gentle boil, then immediately reduce the heat to medium-low and simmer for 8-10 minutes. This simmering time allows the tomatoes to break down further, the flour to fully incorporate and thicken the soup, and all the flavors to meld together beautifully. I find that letting it bubble gently rather than rapidly boiling keeps the flavors more vibrant and prevents the soup from becoming too thick too quickly.

Carefully transfer the soup to a blender in batches, filling it no more than halfway each time to prevent splashing and burning yourself—hot soup expands when blended. Blend each batch until completely smooth and creamy, about 1-2 minutes per batch. Pour the pureed soup back into the pot as you finish each batch. This blending step transforms the chunky tomato mixture into a silky, restaurant-quality soup where all the vegetables are incorporated into the broth itself, creating a luxurious mouthfeel.

Return the pot to medium heat and stir in the heavy cream and kosher salt, then add the shredded cooked chicken. Stir frequently and heat through for 2-3 minutes until the soup is steaming and the chicken is warmed throughout. Taste a spoonful and adjust the seasoning with additional salt and freshly cracked black pepper as needed—the cream will mellow the acidity of the tomatoes, so you may need a touch more salt than you'd expect. I recommend adding the salt in two stages (some upfront, then adjusting at the end) because the cream changes how the salt is perceived on your palate.

Ladle the soup into bowls and serve immediately. The soup is now ready to eat, with all the comforting flavors of chicken and tomato coming together in a creamy, satisfying bowl.