The Greek legend of Icarus was just a myth from an engineering point of view; clearly with wax and feathers one cannot get very far.
Leonardo Da Vinci left several construction drawings about flying devices and, according to Girolamo Cardano in his De Subtilitate he tried but failed to get airborne in Milan, then he tried second time at Mt Ceceri at Peretola, near Florence. The pilot in both cases could have been Tommaso Masini, nicknamed Zoroaster, a native of Peretola, so much so the people of Peretola put a commemorative slab about such first successful human flight, even if there are no proofs about it.
What seems certain is that the Chinese were flying long before the time of Leonardo and we have an extraordinary witness testifying it: Marco Polo (1254–1324). In China, giant kites were built since the third century BC, which were capable of lifting men off the ground. Joseph Needham in his monumental work on Science and Civilization in China elaborate this point: see Needham, Science and Civilization in China, vol. IV, pp. 576–80. There is overwhelming evidence proving that the Chinese were the first to having a man airborne.
First let us explain why so few people, even Chinese, know about Marco Polo’s description of human flight. When Marco Polo dictated his memoirs, while a captive of the Genoese, to Rustichello da Pisa who noted them down in a sort of French, they were a great success and were copied and passed around. But when the first edition of il Milione of Marco Polo went into print in 1496 as the Livre que est appellé le Divisement dou monde de Marc Pol the editor had to decide which manuscript was trustable and which was not, choosing among several. The point about men flying in China was thus left out for unknown reasons.
This passage was later inserted into it for the first time with the book Marco Polo The Description of the World, Moule and Palliot, vol. I, 1938. pp. 356 ff. This edition is today considered the most complete and most authoritative translation of the book of Marco Polo and it include also a manuscript that was found by Sir Percival David (1892–1964) in the Cathedral de Toledo, in Spain.
That manuscript was a Latin copy written in 1795 based on a manuscript dating to about 1400. Arthur Christopher Moule transcribed it and complete with the Latin text was published in 1935. A. C. Moule combined seventeen different versions of the Marco Polo manuscripts into one document and put all words that are not found in the other versions into italics, an extraordinary scholarly achievement!
Here is the passage of Chinese flying men as Marco Polo had seen them in China:
And so we will tell you how when any ship must go on a voyage, they prove whether her business will go well or ill. The men of the ship will have a hurdle, that is a grating, of withers, and at each corner and side of this framework will be tied a cord, so that there be eight cords, and they will all be tied at the other end to a long rope.
Next they will find some fool or drunkard and they will bind him on the hurdle, since no one in his right mind or with his wits about him would expose himself to that peril. And this is done when a strong wind prevails.
Then the framework being set up opposite the wind, the wind lifts it and carries it up into the sky, while the men hold on by the long rope. And if, while it is in the air, the hurdle leans towards the way of the wind, they pull the rope to them a little so that it is set again upright, after which they let out some more rope and it rises higher. And if again it tips, once more they pull in the rope until the frame is upright and climbing, and then they yield rope again, so that in this manner it would rise so high that it could not be seen, if only the rope were long enough.
The augury they interpret thus: if the hurdle going straight up makes for the sky, they say that the ship for which the test has been made will have a quick and prosperous voyage, whereupon all the merchants run together for the sake of sailing and going with her. But if the hurdle has not been able to go up, no merchant will be willing to enter the ship for which the test has been made, because they say that she could not finish her voyage and would be oppressed by many ills. And so that ship stays in port that year.
Chinese were using kites, perhaps train of kites or, as we call them today, power-kites.