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Bring a pot of salted water to a boil, and cook pasta according to the package directions. Drain the pasta, reserving 1 cup of the cooking water.
While the pasta is cooking, season the chicken on both sides with half of the salt and pepper.
Heat 2 tablespoons of the olive oil in a large, deep skillet over medium heat. When the oil is shimmering, add the chicken in a single layer and sear for 3 minutes per side, or until cooked through.
You may have to cook the chicken in batches. Transfer the chicken to a cutting board, and allow it to rest for 5 minutes, before slicing it into strips.
While the chicken is cooling, heat the remaining tablespoon of olive oil in the skillet, and add the asparagus and cherry tomatoes. Add in the garlic and sauté. Stirring often, for 2-3 minutes, or until the asparagus is tender-crisp.
Add 1 cup of the reserved pasta cooking water to the skillet, pesto, and the sliced chicken, and bring the liquid to a simmer.
As soon as it starts bubbling, add the cooked pasta, and toss with tongs to coat the noodles in the sauce. Remove from the heat and serve immediately.