Heat a grill pan over medium-high heat. Place chicken between 2 sheets of plastic wrap, and pound to an even thickness using a meat mallet or small heavy skillet. Sprinkle both sides of chicken evenly with chili powder and salt. Lightly coat chicken with cooking spray. Add chicken to pan; cook for 3 minutes on each side or until done. Remove from pan; set aside.
Combine half of pineapple, cilantro, orange juice, vinegar, habanero, and garlic in a blender; process until smooth. With blender on, gradually add olive oil until blended.
Combine remaining pineapple, jicama, and the remaining ingredients in a large bowl. Drizzle with 3/4 cup dressing, and toss gently to coat. Divide salad evenly among 4 plates. Cut chicken across the grain into thin slices; divide chicken evenly over salads. Drizzle salads evenly with remaining 1/4 cup dressing.