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Preheat the oven to 375°F / 190°C.
If using large chicken breasts, cut them in half, lengthwise. Working one by one, cover with cling film and pound each cutlet to a 1/5'' (0.5cm) thickness. Season both sides with salt and pepper.
Place 2 slices of bacon on your working surface, then add one piece of thin chicken on top.
Add about 1 Tbsp of pesto sauce in the center, spread it, and sprinkle with shredded cheese.
Roll up the chicken tightly and seal the ends through the bacon with a toothpick. Repeat with the remaining chicken cutlets.
Heat oil in an ovenproof skillet over medium heat. Add the chicken roll-ups and sear on all sides until golden, about 6-8 minutes.
Add cherry tomatoes, then take the skillet from the stove and place it into the oven. Continue to cook for 13-15 minutes, or until the chicken is cooked through (internal temp of chicken should read 165°F / 75°C on a cooking thermometer).
Garnish with fresh chopped herbs and enjoy while hot!