The President also announced hefty tax cuts for businesses and individuals which would nearly double the personal tax-free allowance to $12,000.
But critics claim his plans favour big business and the super rich, while some analysts have warned they could cost trillions in the long term.
Speaking to an enthusiastic crowd in Indianapolis last night, Mr Trump described his proposals as a “once-in-a-generation” chance.
He said: “We’re going to cut taxes for the middle class, make the tax code simpler and more fair for everyday Americans, and we are going to bring back the jobs and wealth that have left our country — and most people thought left our country for good.
“These tax cuts are significant. There’s never been tax cuts like what we’re talking about.”
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Every US citizen who earns more than $6,350 is required to file a lengthy federal tax return – similar to a self assessment in the UK – every year.
Mr Trump’s changes would reduce the number of tax brackets from seven to three and would in theory make the process of paying taxes far easier.
The real estate mogul said this would allow most American families to file their taxes on a “single sheet of paper”.
He added: “The current tax system is a colossal barrier standing in the way of America’s economic comeback because it can be far greater than it’s ever been.
“But we’re going to remove that barrier to create the tax system our people finally, finally, finally — and want and deserve.”
Mr Trump insisted his overhaul was not for the benefit of the “wealthy or well-connected”.
But a review published by Bloomberg concluded his proposed scrapping of the estate tax – similar to the UK’s inheritance tax – would result in a multi-million dollar tax cut for the President and his billionaire cabinet.
The former reality TV star has consistently refused to release his tax returns – something every President has done for more than four decades – so it is impossible to tell exactly how much his proposals would save him.
Mr Trump’s Republican party has a slim majority in Congress, and his plans will need to face several difficult votes before they become law.
Republican Senator Bob Corker told reporters earlier this week he would oppose any proposals that were funded with borrowed money.
He said: “What I can tell you is that I’m not about to vote for any bill that increases our deficit, period.”