Start by heating a large cast iron pan or other oven safe skillet over medium heat. Dice bacon while the pan is heating.
Once the pan is hot, add in the diced bacon to cook. Cook it for 6-7 minutes until it is just starting to get cooked around the edges and then remove it and place on a paper towel lined plate. It will cook the rest of the way in the oven.
Preheat the oven to 400° Fahrenheit.
While the bacon is cooking, cut the pear into slices and place it in a bowl. Cut the squash in half lengthwise and scoop out the seeds. Cut crosswise into 1/4-inch slices. Add squash slices to the bowl with pears.
Add in the avocado oil, rosemary, cayenne pepper and 1/2 tsp salt and 1/2 tsp pepper to the bowl. Mix everything together to coat.
Season the chicken with salt and pepper.
Once the bacon is cooked, remove it from the pan and set aside. Pour off excess bacon grease if desired, but leave some in the pan to cook the chicken in.
Place the chicken in the skillet to brown. Cook for five minutes and flip, cooking for another 5 minutes. Remove from heat.
Add in the squash and pear mixture to the skillet around and over the chicken (it will be pretty full). Sprinkle the bacon on top.
Carefully transfer the skillet to the oven.
Bake for 25-30 minutes, depending on the size of your chicken breasts, until the chicken is cooked completely through in the middle.
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