Preheat the oven to 275 degrees.
Season both sides of the ribeye steaks with Chicago Steak Company seasoning and Worcestershire sauce. Lightly press seasoning into steak.
Place steaks on a metal rack on top of a baking tray and put into the oven.
Cook until steaks reach an internal temperature of 110-degress for a medium rare doneness. Depending on the thickness of the ribeye it can take between 30-60 minutes.
Remove meat from the oven and let rest for 5-10 minutes to allow the juices to disperse throughout the steak.
Add EVOO olive oil to your cast iron skillet and heat up on the stove top. Wait until the oil is scalding hot before adding the steaks.
Add the ribeyes to the skillet and allow the bottom side to brown up. This should take between 45 and 75 seconds. Flip the steaks and do the same to the other side.
Once both sides are browned, turn the steaks on their sides to allow the edges to brown up.