The last American to win the men's race was Khalid Khannouchi in 2002.The women's race was won by Ethiopian Tirunesh Dibaba in 2 hours 18 minutes and 31 seconds.
Rupp, competing in just his fourth marathon, surged clear of the rest of field in a tactical race with a 24th mile recorded in just 4min 30sec.
"It's incredible. I trained so hard, day in day out, so to win a big race like this in a special place which is where my dad grew up, words can't describe how good it feels", an overjoyed Rupp said afterwards. At the halfway point the lead group came in 1:06:06. She missed the course record but clocked her second-fastest time ever.
Jordan Hasay, a 26-year-old from Fontana, California, came close to matching the feat in the women's race.
Hasay, who trains with Rupp under Alberto Salazar, was third in the Boston Marathon to give the US its best combined male-female finish since 1985.
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The World Marathon Majors continue on November 5 with the New York City Marathon.
As Dibaba had more than a minute lead at the 40K mark, she was never in danger of finishing outside of the winner's circle.
Abel Kiri finished second in 2:09:48 with Bernard Kipyego third in 2:10:23.
Rupp, the Rio Olympics bronze medalist broke away from Kirui in the final 10kilometres of the race and ensured he finished off the year on high note with a personal best time having finished second at the Boston Marathon earlier on in the year.
Stay tuned for top Canadian results from the 2017 Chicago Marathon.