Line a baking sheet with parchment paper and set aside. Next, slice the Cara Cara Oranges into 1/4" slices removing any seeds.
In a wide, large skillet combine granulated sugar and water. Bring the skillet to a boil and continue continue to whisk until the sugar has dissolved. Next, add the orange slices to the skillet and lay in an even layer. Bring the skillet to a simmer. Let the orange slices simmer for about 1 hour uncovered or until they become transparent.
Once the orange slices have become transparent, place the slices on the baking sheet lined with parchment paper. Let the orange slices dry for at least 24 hours uncovered. They will still feel a bit sticky but that's okay.
Next, place the chocolate chips in a microwave safe bowl and melt on high for 10 to 15 second intervals. Once melted, dip half an orange slice into the chocolate and place back on the parchment paper to set. Sprinkle with sea salt if desired. Repeat process until all orange slices have been dipped. Wait for about 15 minutes until the chocolate hardens to serve.