Please tell friend of mine why. Waikiki reminds him of Chicago but with a beach. He loves Chicago and returns there often but he would never want to return to Waikiki. It was the first time I heard someone doesn't wish to return to Honolulu.

I am not sure what cultural attractions outside of the small annex of the Bishop Museum are in Waikiki. Honolulu proper is a different story though. My point is that you can?t really compare a section of Honolulu to the entirety of a city somewhere else.

Dimes to donuts though anyone who describes Honolulu as Waikiki does not know anything about cultural attractions anywhere , so I am not sure if your friend would understand my point.
So does it matter? I would not venture to Chicago unless I needed to go. Just too many more options in this country and beyond. Everyone has different expectations of a vacation, to each his/her own.

I've been to both places and don't get the comparison, however, in January I am headed back to Waikiki and will give it some thought...over a Mai Tai

If your friends visit to Oahu ONLY included Waikiki then I can understand his disappointment. Anyone who actually explores Oahu will tell you it is one of the more diverse islands with the best beaches of all the Hawaiian islands.

Thank you for your comments. We just told him he should go back to Oahu and check out what's beyond Waikiki