Chicago is a laggard in this department. It is an insanely busy airport that brings in plenty of revenue, some of which can be diverted to swallowing the cost for free public wi-fi. If dozens of other major US airports can do it, ORD sure as hell can.
In the year 2014, where internet connectivity is a necessity (especially for business travelers who might want to accomplish some work on layovers), free wi-fi is a DUH proposition.
By the way, isn't Chicago supposed to be a "progressive" or forward-thinking city? Heck, they even released llamas and goats into the airport fields to clear away the brush, so talk about being granola. Mayor Emanuel wants to make the city the most bike-friendly in the country. The city's efforts to cultivate this progressive image doesn't jive with the paywall policy.
Obviously, the city is more concerned with raising more revenue in the short-term. Withe competing pressures from other airports, I think the paywall will fall in due time.