The former president was invited to be a guest speaker in a conversation moderated by Bloomberg Editor-in-Chief John Micklethwait.
Harris was also invited to attend the event. Trump was the only one to confirm his attendance.
Trump was engaging but also combative at times during the hour-long interview. IN what appeared to be a rather friendly audience at a downtown hotel, Trump stood his ground on his economic policies and immigration, getting frequent cheers.
The interview started 48 minutes late, but he still got a warm welcome and a standing ovation.
Donald Trump defends tariffs, mass deportations in Chicago interview
"I like that crowd, that's a nice group of people," Trump said as he took his seat.
He unabashedly defended his "America first" plan that calls for high tariffs on some foreign trade.
"We're going to bring the companies back with lower taxes, still further for companies that are going to make that product in the USA. We're going to protect those companies with strong tariffs because I'm a believer in tariffs," Trump said. "To me the most beautiful word in the dictionary is tariff. It's my favorite word. It needs a public relations firm."
A consensus of economists have criticized that plan, saying tariffs will increase inflation, raise the national debt and hurt consumers, but Trump dismissed those concerns. Supports hope if he is elected, he would use tariffs judiciously.
"I'm an economics major by trade. So tariffs are usually a bad thing. I like them to create some fairness and some, a level playing field, not necessarily to punish," said real estate investor Dean Kelly.
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Trump was asked whether he was OK with the economy shrinking if he follows through with his mass deportation plan for undocumented workers.
"I want a lot of people to come into our country, but I want them to come in legally," Trump said.
"I do like his policies. I like what he's talking about, is it gonna be as easy to execute as he says he it is. I don't know about that, but for the most part, that that is kind of what the crowd wanted to hear," said Cynthia Francque of Park Ridge.
Trump also again downplayed the insurrection on January 6 when asked about whether he supports a peaceful transfer of power, which he would not commit to.
"We want to have honest elections. You think the last election was honest?" he deflected.
Trump also made a cautious prediction on which states will decide the outcome of the election.
"So they say Pennsylvania I would say most, I think we're doing very well there. I think you look at Michigan too," he said.
Trump was asked if, as a businessman, he would hire a 78-year-old to be CEO and he said yes. He said cognitive tests are important he clamed Vice President Kamala Harris would not pass one.
On the issue of inflation, he advocated for presidential input on interest rates, which are current determined by the Federal Reserve.
"I think I have the right to say I think you should go up or down a little bit, I don't think I should be allowed to order it, but I think I have the right to put in comments," he said.
Sixteen Nobel Prize-winning economists signed a letter in June expressing fear that Trump's proposals would "reignite'' inflation, which has plummeted since peaking at 9.1% in 2022 and is nearly back to the Fed's 2% target.
The Nobel economists noted that they aren't alone in sounding the alarm.
"Nonpartisan researchers," they said, "predict that if Donald Trump successfully enacts his agenda, it will increase inflation."
Last month, the Peterson Institute for International Economics predicted that Trump's policies - the deportations, import taxes and efforts to erode the Fed's independence - would drive consumer prices sharply higher two years into his second term. Peterson's analysis concluded that inflation, which would otherwise register 1.9% in 2026, would instead jump to between 6% and 9.3% if Trump's economic proposals were adopted.
Trump's plans have been roundly criticized by both Illinois Governor JB Pritzker, and Chicago Mayor Brandon Johnson. Pritzker released a statement after the interview saying, in part, "Today, Donald Trump reminded voters of who he really is: a rambling, incoherent, insulting old man determined to drive our economy into the deepest ditch he can find. Donald Trump's proposed economic policies would increase costs, deepen the deficit, and kill jobs yet Trump continues to double down on them. Why? Because Trump doesn't care about American workers or American jobs, he only cares about himself and his wealthiest donors."
On Monday, vice presidential candidate JD Vance was also in the Chicago area for a private fundraising event.
Governor Pritzker issued the following statement on Trump's visit before his appearance:
"Every time he opens his mouth, Donald Trump reminds us that he is a racist, misogynist 34-time convicted felon who doesn't care about anyone but himself. On a recent visit to Chicago, he spewed insults at Kamala Harris and no doubt we'll hear it again today as he tries to peddle his economic plans that would raise costs for American families by $4,000, spike inflation, and kill jobs. But a majority of Americans reject those policies and the other disastrous, dangerous Project 2025 proposals a second Trump administration would plague this country with. On November 5th, voters will make that very clear when we send Donald Trump and his MAGA extremism packing."
Mayor Johnson also issued a statement:
"Chicagoans know Donald Trump all too well. Last time he was in our city, Trump deployed shameful dog whistle rhetoric casting doubt on Vice President Kamala Harris's heritage. Now, he's back with his 'economic plan' which is nothing more than a massive tax break for billionaires and big corporations while working people get stuck with higher prices for everyday goods because of his foolish tariff proposals. Meanwhile, Trump relentlessly attacks reproductive freedom, affordable healthcare, Social Security and Medicare, our environment, the labor movement, and the foundations of our democracy itself. Chicagoans overwhelmingly stand with Kamala Harris and Tim Walz, and in three weeks Trump and his Project 2025 agenda will be rejected once and for all."
The Associated Press contributed to this report.