United grew to daily services but soon pulled back to seasonal flying.
As part of the Chicago deal, United will return to a year-round flying.
The agreement was also brokered before the retirement of an enthusiastic supporter of links to New Zealand, United's senior vice-president of worldwide sales Dave Hilfman.
Air New Zealand also needed to have sufficient fleet flexibility but now has that with new Dreamliners joining the fleet and by the time of launch of the route in November its Rolls-Royce engine issues will be behind it.
There is another peripheral personal link to the Windy City. While Christopher Luxon was working at Unilever he was based in the wider Chicago area and is fond of the area, something he recalled while introducing one-time Illinois State Senator Barack Obama at the big private dinner function last week.
But this is purely a commercial decision and a smart one. More than 200,000 Kiwis a year fly to the United States and many now go way beyond traditional Californian favourite spots.
Houston worked as an entry into the southern and eastern states and Chicago is a much more attractive destination in itself, but also a great launch pad for Kiwis heading for Canada and the northeast of the US with popular cities Washington and New York.
They are around a two-hour flight from Chicago's O'Hare International Airport, by all accounts a much more pleasant place to enter the US than Los Angeles.
New Zealand will also seem a lot closer for wealthy keen travellers who live along the US east coast. These tourists tend to travel further and wider when they reach a destination.
Air New Zealand says the new route could be worth $70 million to this country's economy and, as it cops flak for retreating from some regional destinations, it makes the point half of this will be spent outside the main centres.
Whether a new non-stop service to Chicago will do much to assuage anger in affected regions is another matter, but Kiwis planning a US trip, and the tourist industry, will be smiling.