Some airports are just terrible and it doesn't make any sense with the traffic they receive why they don't just spend the money. Ohare has semi permanent buckets to catch leaks from that notorious roof. We welcome people into the U.S. at these airports and that's the first thing they see off the plane, the ceiling pissing water in Ohare even on a sunny day.
Terminal 5 (International arrivals) doesn't have the leaking Helmut Jahn ceilings like T1, but it also has absolutely zero amenities between the gates and customs.
And, when you do exit, there is a single shitty McDonald's with no room to sit down and eat. There might be a Starbucks too now.
Why would the airport CEO spend money to fix O'Hare that could go to his bonus? What are you going to do about it? To transition to a new airport entirely (like Atlanta's Hartsfield-Jackson did to O'Hare) will take long enough for it to be the next CEO's bonus that will be affected.
US airports do not operate at the whims of the CEO. Most infrastructure investments are either championed by the airlines or by whatever government entity oversees the airport authority.