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In a food processor pulse basil, garlic, parmesan cheese, salt and pepper until smooth. Slowly add the olive oil while pulsing.
Combine the raw chicken with pesto and marinate a few hours in a bowl.
Soak wooden skewers in water at least 30 minutes (or use metal ones to avoid this step).
Beginning and ending with chicken, thread chicken and tomatoes onto 8 pairs of parallel skewers to make 8 kebabs total.
Heat the outdoor grill or indoor grill pan over medium heat until hot. Be sure the grates are clean and spray lightly with oil.
Place the chicken on the hot grill and cook about 3-4 minutes; turn and continue cooking until chicken is cooked through, about 2 to 3 minutes.