Place the chicken in a large freezer bag along with two tablespoons of Italian dressing. Seal tightly and turn each breast until coated on both sides. Place in the refrigerator for at least 30 minutes, turning once halfway through.
Add the removable rack to the Instant Pot® cooking container and place the marinated breasts on top. Add water and sprinkle each breast with the garlic and onion powder. Season with salt and black pepper, to taste.
Add the lid and lock it into place. Position the vent to “Sealing” and set the “Manual” setting to 8 minutes.
While the chicken is cooking, prepare the tortellini according to package instructions. (Add olive oil to the cooking water as instructed on the package to prevent sticking). Rinse and drain well, and transfer to a large mixing bowl.
When cook time is complete on the Instant Pot®, allow pressure to release naturally for 10 minutes, then manually release any remaining pressure. Remove the lid and transfer the chicken to a non-permeable cutting board.
.When the chicken is cool enough to handle, cut into one-inch cubes and transfer to the bowl with the tortellini.
Add the olives and tomatoes to the bowl, along with two tablespoons of Italian dressing. Lightly season with salt and black pepper, to taste. Gently fold the ingredients with a spoon until thoroughly coated in the dressing.
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Using 10-12” wooden skewers, thread 1 black olive, 1 grape tomato half, 1 chicken cube, 1 tortellini, 1 chicken cube, 1 tortellini, 1 tomato half, and 1 black olive. Repeat this process until all skewers are complete.
Note: The order listed above is just a suggestion. It looks nice if you begin and end each skewer with the same ingredients, but your preferences may vary.
Tip: When finished assembling the skewers, toss any remaining ingredients in a medium bowl with a little Italian dressing to serve on the side.
To serve, transfer the finished skewers to a platter and offer the remaining Italian dressing on the side. Enjoy!