Preheat oven to 450°F.
Spread tomatoes, garlic cloves and onions onto baking tray. Drizzle with ½ cup of olive oil and season with salt and pepper. Roast for 20 to 30 minutes, or until caramelized.
Remove roasted tomatoes, garlic and onion from oven and transfer to large stock pot (set aside the roasted tomatoes for later). Add 3/4 of the chicken stock, bay leaves, and butter.
Bring to a boil, reduce heat and simmer for 15 to 20 minutes or until liquid has reduced by a third.
Wash and dry basil leaves, if using, and add to the pot. Use an immersion blender to purée soup until smooth. Chill on a bowl of ice for 15 minutes or refrigerate for several hours.
Garnish with diced Pure Flavor® seedless cucumbers or sweet bell peppers for an extra touch.