The 31-year-old Oregon native, who finished second at the 2017 Boston Marathon, completed the course in 2 hours, 9 minutes and 20 seconds on Sunday, 28 seconds ahead of the defending champion, Kenyan runner Abel Kirui, reports Efe news agency.
The last time a US male competitor won in Chicago was in 2002, when Khalid Khannouchi took the trophy.
Rupp, who won the bronze medal in the men's marathon at the 2016 Rio de Janeiro Olympics, surpassed Kirui and the other favourites with roughly 7 kilometres (4.3 miles) left in the race.
At the 2012 London Olympics, Rupp made history as the first US runner to win a medal -- he took the silver -- in the men's 10,000m race since 1964.
"It's just incredible. You train so hard year in and year out, day in and day out and to have a race like this where it all comes together and be able to win in a city that really is such a special place to me, given that my dad grew up here -- words can't express the feeling of crossing the line," he said after winning Sunday's race.
Dibaba, a 2008 Olympic gold medallist, triumphed in the women's race with a time of 2.18:31.
Kenya's Brigid Kosgei was second, trailing Dibaba by more than two minutes. Third place went to American Jordan Hasay, who set a new US record with a time of 2.20:57.
This year's 40th Chicago Marathon attracted 44,000 participants, the most ever.
(This story has not been edited by Social News XYZ staff and is auto-generated from a syndicated feed.)
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