34-year-old Windass spent 4 years at Boothferry Park under Terry Dolan's reign in the early 90s before moving on, and had been linked with a return to City after leaving Sheffield United.
However, Peter Taylor turned down the chance to bring 'Deano' back to Hull, and he will instead sign a two-year deal at Bradford.
He said: "I'm not going back to Bradford for the comfort zone. If I'd wanted to do that, I could have gone somewhere else and earned a lot more money.
"I could have stayed at Sheffield United for that but this is not about money. All I want to do is play and I'm delighted that Nicky Law is going to give me that chance.
"I don't want to get in any bother but I love proving people wrong and I want to show Neil Warnock he made a mistake. I've had a lot of good vibes from Nicky about the club and he really sold it to me."
Meanwhile, Paul Fewings - who came through City's youth system and was briefly a team-mate of Windass - has signed for Kettering Town. The 25-year-old forward scored just 3 times in the black and amber between 1995-98, and then had spells at Hereford, Boston, Chesham and Billericay. Carlin Intonga - who had a trial spell with City during pre-season last year - is another ex-Tiger at Rockingham Road.