
Grilled Balsamic Chicken with Basil Mashed Potatoes is the perfect transitional meal from summer to fall. Featuring creamy, garlicky mashed potatoes hinted with fresh basil, juicy balsamic grilled chicken, roasted tomatoes, and balsamic glaze to top it all off. It's comforting, yet still feels fresh and jam-packed with flavor. Simple enough for a weeknight dinner but also lovely to serve to guests! Everyone goes nuts for this one.
Begin by marinating the chicken. In a gallon sized bag or large bowl, whisk together the balsamic vinegar, olive oil, garlic, honey, dijon, Italian seasoning, salt, pepper, and red pepper flakes. Add the chicken and marinate overnight or for at least 4 hours.
Once chicken has marinated, make the mashed potatoes. Add the potatoes to a large pot and cover with water. Season the water liberally with a couple of big pinches of salt. Bring to a boil and cook for 20 minutes or so, or until potatoes are fork tender.
While potatoes are boiling, heat the milk and one of the garlic cloves in a small saucepan over medium-high heat until it comes to a simmer (watch carefully, the milk can burn quickly!). Once simmering, reduce heat to medium-low, and let the milk and garlic steep for 15-20 minutes, while the potatoes are cooking. Once finished, discard the garlic cloves.
Heat the butter in a medium saucepan over medium heat and add the remaining 3 garlic cloves (finely chopped). Sauté for a minute or so, until fragrant. Set aside.
Make the garlic roasted tomatoes. Preheat oven to 400℉. Place tomatoes and smashed garlic cloves on a rimmed baking sheet and toss with olive oil, salt, and pepper. Roast for 15 minutes, until tomatoes have become burst, shriveled, and slightly caramelized on the edges. Discard the garlic cloves (or save for another use!).
Once potatoes are finished cooking, drain. Add back into the pot with the steeped milk, garlic butter mixture, sour cream, salt, and pepper. Mash until desired consistency has been reached. Stir in the basil. Season to taste with additional salt and pepper, if needed.
Preheat your grill to medium - high heat. Grill the chicken for 4-5 minutes per side, depending on the size until cooked through. Let rest for 10 minutes before slicing.
To serve, arrange the sliced grilled chicken on a pile of mashed potatoes. Scatter with a spoonful of the garlicky roasted tomatoes. Finish with fresh basil leaves, a drizzle of balsamic glaze, a sprinkle of flaky salt, and freshly cracked black pepper to taste. Enjoy!