Heat a deep pot over medium to medium-high heat. Add oil and potatoes. Cover and cook 5 minutes, stirring frequently.
Add onion, celery, red bell pepper, and bay leaves. Season with Old Bay, salt and pepper. Cover and reduce heat a bit, cook a few minutes more, stirring occasionally.
Uncover and whisk in flour. Cook a minute more. Add corn, broth, and milk. Bring soup to a boil, reduce heat, and simmer, 7 to 10 minutes, to thicken. Adjust seasonings and serve bowls of chowder with a sprinkle of chopped scallions and oyster crackers.