Brush both sides of the pineapple slices with olive oil and sprinkle with salt and pepper. Grill the pineapple until caramelized on both sides, about 4-5 minutes per side, rotating once. Remove from grill and dice into bite-sized pieces.
In a large bowl, toss together diced grilled pineapple with onion, cilantro, jalepeño and lime juice. Check for seasoning and add salt and pepper to taste. Serve with tortilla chips.