Before becoming Honolulu Harry's Waikiki, this location was the Barrel O' Fun Tavern, John Dillinger's favorite hangout.
From its opening in 1949 (putting it squarely in the pre-tiki category), Honolulu Harry’s Waikiki provided “entertainment direct from Hawaii” and “dancing under Hawaiian skies.”
By 1959, its owner escalated the restaurant to an “authentic Hawaiian theatre restaurant.” Souvenir photos dated as late as 1960 have popped up (see below).
It stood on the corner of Clarendon and Wilson in uptown Chicago. “There were fresh pineapples on the tables, paper leis and ti leaves hanging all around”.
It appears in later years before it closed that the name might have just been shortened to "Club Waikiki". Matchbooks with the same address point in that direction. Alternately, it's possible this club was just a section of the larger complex like Don the Beachcomber's had its Dagger Bar, for instance.
Today, the site is home to The Covington Luxury Apartments, which were built in 1965, so Harry's must have closed some time between 1960 and 1965.