In a large dutch oven, add the olive oil and heat over medium high heat. Add the carrots, onions, garlic and 1/2 teaspoon kosher salt and stir to combine. Saute the vegetables until the carrots are softened and the onions start to take on a translucent look, about 8-10 minutes.
Add the tomatoes, chicken broth, basil, red pepper flakes and sugar. With a wooden spoon crush the tomatoes to break them apart. Heat to boiling, then reduce heat to a low simmer and place the lid on the pot loosely so that the steam can escape. Simmer for 20 minutes.
Remove from heat. Working in batches, transfer the soup to a blender and puree until smooth.
Return the soup to the pot. Stir in the half and half and orzo. Add additional 1/2 teaspoon kosher salt and black pepper. Check the seasoning and adjust as necessary.