Chicago is preparing to sell approximately $1 billion in debt owed to the city from unpaid parking tickets and other sources. Bloomberg posted on X that a senior finance official has cautioned that this unprecedented move may incur significant costs and face uncertain interest from investors. The city's decision to offload this debt comes as it seeks to manage its financial obligations and improve its fiscal health. However, the potential challenges in attracting investors could impact the success of the offering. The city aims to address its budgetary needs while navigating the complexities of the debt market.