Investment Firm Selling Airline Amid Chicago Parking Meter Deal

A New York-based investment firm, Stonepeak Partners, which is set to acquire Chicago’s parking meters, announced on September 28, 2026, that it has sold Omni Air International, an airline involved in deportation flights for the Trump administration. The sale to OAI Holdings, LLC follows Stonepeak's request for the City Council's approval of a $2.53 billion deal for the parking meters, which has faced significant opposition from progressive council members. These members indicated they would not support the parking meter sale unless Omni Air was sold. Stonepeak, which leased the parking meters for 75 years in 2008, has been under pressure to divest from Omni Air due to its contract with the Department of Homeland Security. ATSG CEO Greg Mays stated that the sale aligns with the company's strategy to focus on air cargo services. A deal negotiated by a group of alderpeople requires Stonepeak to sell Omni Air, pay the city $75 million, and share 5% of its profits, potentially yielding $376.2 million for the city over 57 years. Stonepeak's senior managing director, James Wyper, expressed that the firm's stance on the Trump administration's deportation efforts was negative. The City Council is expected to vote on the parking meter sale soon, with some members raising concerns about the details of the agreement and the potential for Stonepeak to not fulfill the sale of Omni Air.