Slice the ends off of the Brussels Sprouts and then cut in half. Drizzle a tablespoon of olive oil on a large rimmed baking sheet. Place the Brussels sprouts on one side of the pan. Then, place the butternut squash on the other side of the pan. Drizzle the vegetables with one tablespoon olive oil and mix.
Then place the chicken breast in parchment paper and flatten with a meat mallet until even in size. Sprinkle with salt, pepper, and garlic powder. Flip over and repeat and then sprinkle on one teaspoon of Italian seasoning between the two chicken breasts. Place the chicken breast in the empty part of the baking sheet and then drizzle with remaining one tablespoon olive oil. Place the sheet pan in the oven.
While the chicken and vegetables are baking. Place the balsamic vinegar, honey, and the remaining Italian seasoning in a sauce pan. Mix well, and simmer on medium-low heat for 5 minutes. Then remove from the heat and let it thicken.
Next, place the ¼ cup of dried cranberries in a bowl and fill the bowl with water until just covered. Drain, and sprinkle over the brussels sprouts during the last 2 minutes of baking. Carefully remove the baking sheet, divide evenly among two plates and drizzle balsamic honey reduction on top of the chicken and vegetables and enjoy.