I think Chicago is a good choice for his library. It's where he built his career and started his family. I gave up a scholarship to the Chicago Art Institute when I was going to be drafted....my nephew decades later got the same scholarship and made his life in Chicago. He loves it there.
If you've ever lived in Hawaii, it's a really, really small place....not having tourists where you plan to retire might be a good thing. I think Obama will probably retire in the islands.