Prepare grill to high heat.
Combine 1 tablespoon oil, vinegar, salt, and pepper in a large bowl. Add radicchio, fennel, endive, and grapes; toss gently to coat. Set aside.
Brush remaining 1 1/2 teaspoons oil over cut sides of figs. Place figs on a grill rack coated with cooking spray; grill 1 1/2 minutes on each side or until lightly browned. Place radicchio mixture on a platter; top with grilled figs.