Rupp, who is a former track star and three-time Olympian, finished the Boston Marathon in second place previous year and became the first American since 1964 to win a medal in the 10,000 meters at the 2012 London Olympics.
Rupp, born four years after Meyer's victory, won a 10,000 metres silver medal behind his British training partner Sir Mo Farah at the London 2012 Olympics. She missed the course record but clocked her second-fastest time ever. Only Deena Kastor's 2:19:36 at the 2006 London Marathon is the fastest marathon by an American woman. The women pushed it from the gun, splitting 2:16-2:17 projected pace through the downtown core of Chicago.
It made Rupp the first home victor since Moroccan-born Khalid Khannouchi in 2002 and the first American-born champion since Greg Meyer in 1982.
The men split 1:05:49 through the halfway point while the women were not far back in 1:08:48.
Meanwhile, the women were on course-record pace through 10K, clocking 32:28, including Dibaba, Hasay and Florence Kiplagat, the two-time defending champion. Last year's victor Abel Kirui of Kenya was placed second while marathon record holder Dennis Kimetto did not finish.
The World Marathon Majors continue on November 5 with the New York City Marathon.
By 35K in both races, the lead packs had dwindled. He won the Olympic Trials Marathon in February 2016 in his debut, then claimed Olympic bronze in Rio de Janeiro and finished second in the 2017 Boston Marathon in April.
Kenya has dominated Chicago's marathon, winning 13 of the last 14 races.
Rupp posted the two best miles of the race on Miles 23 and 24, finishing them in 4:35 and 4:31. She finished third again on Sunday in 2:20:57.