Rupp beat out fierce competition, including defending champion Abel Kirui, to take an historic victory and become the first USA victor since Khalid Khannouci won in 2002.
Before the race, Dibaba told reporters that her plan was to break Paula Radcliffe's 2:17:18 course record from 2002. "It's just a great day". Rupp was expected to contend after finishing second in April's Boston Marathon with a time of 2:09:58.
The women's race was won by Ethiopian Tirunesh Dibaba in 2:18:31. "This was very special for me, this was my third marathon and I am pleased because I have learnt a lot", she said after the race. I made the mistake in the past of going out a little too hard too soon and you still have a long ways to go for several miles.
Dibaba and Rupp each took a $100,000 top prize at the 40th anniversary edition of the classic, which saw more than 40,000 runners compete on the streets of the US Midwestern metropolis. It was Dibaba's first career marathon win despite being the third-fastest woman in history, having run 2:17:56 at the 2017 London Marathon.
Kenya has dominated Chicago's marathon, winning 13 of the last 14 races.
The win is also a bounce back for McFadden, who finished fourth at this year's Boston Marathon following surgery for blood clots in February. I really wanted to wait. "When I went I knew I had to put the hammer down, be decisive and go for the finish".
"I just tried to relax and when I make the move be decisive".
But ultimately she came up slightly short of the course record.
Without the use of pacemakers - athletes who are paid to lead portions of the race in hopes of encouraging fast times - the opening splits of the men's race were slow, 2:11 pace to be exact through the first few kilometres.
Dibaba hit the front before the halfway mark and although Kosgei stuck with her for around six miles, the treble Olympic champion opened up a significant lead at the 19-mile stage and there was only going to be one victor. The Kenyan fell back with 10km remaining, leaving Dibaba alone to the end.
Rupp is a three-time U.S. Olympian.
She has won several laurels for the East African country at the Olympics and in other worldwide competitions. A year ago in Rio, Dibaba was third in the 10,000.
The Ethiopian had set her sights on the course record of 2:17:18 and although that proved to be beyond her, Dibaba eased to victory nearly two minutes ahead of Brigid Kosgei of Kenya, while home favourite Jordan Hasay was third.
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