President Donald Trump has publicly blasted Chicago, including dispatching immigration agents to the city in 2025 to track down immigrants without legal status. But his own financial disclosures tell a different story about his relationship with the region: he holds private investments spanning local government bonds and some of the biggest publicly traded companies headquartered in the Chicago area.
Trump's holdings in the Chicago metro area include investments in local government bonds and stock in companies based in the city and elsewhere in Illinois, according to a Chicago Sun-Times review of his economic disclosure statements. Among his reported investments are stakes in McDonald's Corp., which is based in Chicago's West Loop, and Kraft Heinz Co., which has a significant presence in the city. He's also reported investments in Northern Trust, which is based in downtown Chicago, and in United Airlines, headquartered in Chicago as well.
Trump's overall wealth is reportedly believed to be in the billions of dollars, and his portfolio spans financial services, pharmaceuticals, defense, energy, entertainment and health care, per the Sun-Times report. His 2015 financial disclosure, filed when he was running for president, showed he also held investments in Illinois-based firms including Boeing, Caterpillar, Kraft Foods Group and McDonald's, according to the Chicago Tribune.
Bonds Tied to Chicago's Water and Sewer Agency
According to economic disclosure statements, Trump held investments in two Metropolitan Water Reclamation District of Greater Chicago bond issues in 2025. One was valued between $500,001 and $1 million, while the other was valued between $1,000,001 and $5 million, the disclosures show. Both bonds carried a 5 percent interest rate, the Sun-Times reports — one matures in 2028 and the other in 2032.
The water district treats sewage and combats flooding across much of the Chicago region, spanning all of Cook County. It is governed by an elected board of nine members who are all Democrats, and it maintains its own police force. The district borrows money through the bond market to fund capital improvements and sometimes refinance debt.
Officials told the Sun-Times that four MWRD bonds due in 2028 ranged in borrowing amount from $880,000 to $6.9 million, while three bonds due in 2032 ranged from $10 million to more than $48 million — though disclosure records do not identify exactly which bond series Trump invested in. A district spokesman said the agency's credit ratings look strong and indicate a stable financial condition, and added that the district does not know who invests in its bonds. The district's 2026 bond offering of $391.285 million carried ratings of AAA with a stable outlook from Fitch and AA+ with a stable outlook from S&P Global Ratings, and those bonds are direct and general obligations of the district backed by its full faith and credit. The district's 2025 General Corporate Fund posted revenue of $419.781 million against expenditures of $495.334 million, a $75.553 million shortfall before other financing sources, and it carried $2.723 billion in total direct debt as of August 25, 2026, per the same bond filing.
Millions Tied to O'Hare and Midway Airport Debt
Trump had invested in at least five bonds tied to the Chicago Department of Aviation as of 2025, according to disclosure reports cited by the Sun-Times — three linked to O'Hare and two to Midway. The agency oversees both airports. Altogether, his investments in Chicago airport bonds were valued between $250,001 and $5 million, disclosure statements show, with returns of at least 5 percent and maturity dates stretching from 2036 to 2053.
A city official told the Sun-Times that the Midway bonds could have been issued in 2023 or 2025, while the O'Hare bonds could correspond to issuances dating from 2017 through 2025. Airport revenue bonds typically finance capital improvements at O'Hare or Midway — including runway and terminal projects tied to the O'Hare Modernization Program, which revamped the airport's runway system — and sometimes refinance prior airport debt, the official said. Potential bond series matching Trump's holdings ranged in total borrowing from about $2 million to more than $146 million, according to the same city official.
Chicago's own bond records show the scale of its airport borrowing: the city issued $1.10157 billion in O'Hare Series 2025E bonds and $21.725 million in Series 2025G refunding bonds last November, a combined $1.123295 billion, according to the bond offering document. Those bonds are limited obligations of the city, payable from and secured by revenues generated at O'Hare rather than by the city's taxing power, and they carried A+ stable ratings from S&P, Fitch and Kroll, with insured 2025E bonds rated AA stable by S&P. The city's investor relations site lists O'Hare bond issuances dating back to at least 2017.
A Tower on the Chicago River and a Trail of Corporate Stock
Trump also derives significant income from Trump Tower along the Chicago River, which includes condominium units, a hotel and retail space, the Sun-Times reports. His 2015 disclosure, filed through 401 North Wabash Venture LLC — for which he served as member and president — reported the tower generated about $43.3 million in condo sales and more than $5 million in rent since the start of 2014, according to the Tribune's review of that filing.
Beyond Chicago proper, Trump reported an investment in AbbVie Inc., based in North Chicago, valued between $1,000,001 and $5 million. He also reported stakes in ADM, headquartered in Chicago's Loop, valued between $15,001 and $50,000; Conagra Brands, based in Chicago, valued between $50,001 and $100,000; Deere & Co., the farm machinery maker, valued between $500,001 and $1 million; and Exelon Corp., the parent company of ComEd, valued between $100,001 and $250,000. He additionally reported holdings in Illinois Tool Works, based in Glenview, valued between $500,001 and $1 million.
Separately, Trump's most recent annual financial disclosure — received by the Office of Government Ethics on June 29, 2026, after a 45-day filing extension — lists Illinois Tool Works stock valued between $1,001 and $15,000, McDonald's stock between $100,001 and $250,000, Kraft Heinz stock between $15,001 and $50,000, and an Illinois Finance Authority university bond valued between $500,001 and $1 million.
No Comment From the White House or Trump Organization
Trump also reported an investment in a loan benefiting the Wisconsin Dells, a destination that draws many Chicago-area families, valued between $15,001 and $50,000, per the Sun-Times. Before becoming president, Trump used a jetliner bearing his last name for travel and once owned the Trump Shuttle airline.
Both the White House and the Trump Organization declined to comment on the investments when asked by the Sun-Times. Trump and his aides have said that third-party institutions conduct securities trading on his behalf to avoid potential conflicts of interest.
