Kenyan Abel Kirui, the 2016 champion, came in second in 2:09:48. "It's just a great day".
In a race contested in an entirely different manner, fast from the gun, Ethiopia's Tirunesh Dibaba, a three-time Olympic champion and the women's 5,000m world record holder, won in 2:18:30. "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.
Rupp made his move in the 24th mile and there was no catching him as America's wait for a first male victor of the race since Khalid Khannouchi finally ended. "I worked very hard for this".
Kenya has dominated Chicago's marathon, winning 13 of the last 14 races. Dibaba was out in front on her own, having gapped Kosgei, while Kirui, Rupp and Ethiopian Sisay Lemma were in contention duking out who would finish where on the men's podium.
McFadden, who has seven Paralympic gold medals, as well as a silver medal in the marathon in 2016, is the only racer to win all four world major marathons in a single year.
New UKIP leader is Henry Bolton from Kent
Bolton said after his unexpected victory that securing Britain's rapid exit from the European Union is the party's "core task". He had joined Ukip in 2014 having stood for the Liberal Democrats in the 2005 General Election.
"I really wanted to wait", Rupp said. Sunday marked his fourth career marathon. "When I went I knew I had to put the hammer down, be decisive and go for the finish".
But ultimately she came up slightly short of the course record.
Dibaba led after 5km in 16:08, 19 seconds under Radcliffe's course record pace, and had trimmed the field in the lead pack to only five.
Jordan Hasay finished third in 2:20:57 and became the fastest American woman in the Chicago Marathon history.
She has won several laurels for the East African country at the Olympics and in other worldwide competitions.
- Found the head of the journalist that went missing from submarines
- NBA Revamps All-Star Game Format, Captains Choose Teams
- Defense chief says U.S. should stay in nuclear deal with Iran
- Meet the Google Home Mini, a $49 Amazon Echo Dot Alternative
- State, Local Police Raise Awareness Of Breast Cancer With 'Pink Patches'
- Gareth Southgate backs Raheem Sterling to win over England fans
- Where to Celebrate National Taco Day in CT
- Equifax breach under the microscope
- 'Credible Evidence' Former UK PM Sir Edward Heath Was a Pedophile
- All But 3 Dead in Las Vegas Mass Shooting Identified