Put the fingerling potatoes into a medium size pot and cover with filtered water. Boil until fork tender, drain, and set aside.
While the potatoes are boiling, cut the chicken thighs into 3-4 strips each.
Place the chicken thigh strips into a large bowl. Drizzle with the olive oil and add a few generous pinches of sea salt and some freshly ground black pepper. (Yes. Freshly ground black pepper matters. At least to me.) Use your hands to toss the chicken so that it is coated evenly with the oil and seasoning. Place the chicken in a large cast iron skillet or dutch oven or a large baking dish of your choice.
Puncture each cherry tomato with a small knife and combine all the punctured cherry tomatoes in a bowl. Cover with boiling water and allow them to sit for 1 or 2 minutes. Drain the hot water off and carefully pinch the skin off of each tomato.
Add the fingerling potatoes and the skinned cherry tomatoes in with the chicken and gently stir in.
Lastly, combine the fresh oregano, olive oil, and cider vinegar together in a blender or food processor. Blend until just combined – about 15 seconds. Pour this oregano oil over the chicken dish.
Bake in a preheated 400 degree oven for 45 minutes, or until just gently browned on top. Garnish with sea salt, fresh pepper, and some more oregano.