Combine pineapple juice, ketchup, soy sauce, brown sugar, 2 tablespoons of olive oil, rice vinegar, ground ginger, minced garlic, and sesame oil in a medium bowl and whisk until smooth.
Add salt and pepper and stir again.
Transfer cubed chicken to a large Ziploc bag and pour half of the marinade into bag.
Refrigerate for at least 1 hour and soak wood skewers in water for 1 hour as well.
Toss diced vegetables and pineapple in remaining olive oil and assemble skewers by alternating between chicken, red onion, bell pepper, and pineapple.
Brush prepared skewers with remaining marinade and grill over medium heat. Turn and baste kabobs every 5 minutes until chicken is fully cooked, about 15-20 minutes.