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Pat steaks dry and cut into 4 equal portions. Sprinkle with 1/4 teaspoon salt and pepper. Heat 1 tablespoon oil in a large skillet over medium-high heat until very hot, but not smoking. Add the steaks and cook until browned on the bottom, 2 to 4 minutes. Turn over, reduce heat to medium-low and cook to desired doneness, 3 to 5 minutes for medium-rare. Remove the steaks from the pan and set aside, covered with foil.
Heat the remaining 1 teaspoon oil in the pan over medium-low heat. Add grapes and cook, stirring occasionally and pressing down on them with the back of a spoon, until the grapes are brown in spots and mostly broken down, 4 to 6 minutes. Add shallot and cook, stirring, until fragrant, about 1 minute. Sprinkle with flour and stir to coat. Add port, broth, thyme and the remaining 1/4 teaspoon salt. Increase the heat to medium-high and cook, stirring and scraping up any browned bits, until reduced and thickened, 2 to 3 minutes. Serve the steaks with about 3 tablespoons sauce each.