Kaplan Kirsch & Rockwell represented the Chicago Infrastructure Trust (CIT) on behalf of the City of Chicago on its procurement of the O’Hare Express System (OES) Project. The project was conceived to provide express transportation service between Downtown Chicago (the Loop) and O’Hare International Airport. The project scope contemplated that the private partner would design, construct, finance, operate and maintain the resulting airport connection with no City funding subsidy. The CIT and the City of Chicago shortlisted two bidders, including the ultimately successful Elon Musk’s The Boring Company. Although no contract was executed, the Firm helped craft a process that allowed the CIT and the City to evaluate between widely differing proposed technical solutions, while still protecting the City’s interests and accounting for significant technology, regulatory, and right-of-way risk.