After the final ballot was cast, the Second City found itself in fourth place.
In a surprising first round defeat that may have negative implications for President Obama's worldwide clout and Daley's mayoralship here at home, Chicago found its hopes for hosting the Games of the XXXI Olympiad irrevocably dashed.
Rio was pronounced the winner in the final round, besting Madrid in a head-to-head matchup.
Tokyo had been eliminated shortly after Chicago, leaving the two Latin cities in the running.
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"It wasn't our day," said Olympic 2016 CEO Pat Ryan, adding that even though Chicago lost, the city gains a much higher profile on the world stage.
"So Chicagoans can hold their heads high. We're sorry we didn't bring home a victory."
Mayor Daley, speaking three hours after Chicago was eliminated, said he was dissapointed but that he didn't think another bid would be feasible for 2020.
"It's already in this hemisphere, with Rio, and it would not make sense for an American city to try again in 2020," he said. "It's in this hemisphere and they have to move somewhere else."
Daley also mentioned the media for other bid cities were much more behind the bid. Of Oprah, President Obama, and the First Lady, he had nothing but praise.
The voting broke Madrid's way early, with the Spaniards earning 28 votes in the first round to lead Rio (26), Tokyo (22), and Chicago (18).
But in the second round Rio surged ahead, earning 46 votes to Madrid's 29. Tokyo was ejected with only 20 votes.
In the final round, Rio earned 66 votes to win the contract.
Chicago, despite possessing a formidable fundraising machine and impressive bid plan, had in the last week pinned its hopes on Obama's international star power.
Obama's failure to sway the bid in Chicago's favor, some say, weakens his standing both internationally and at home, where he's already facing a difficult health care battle with Congress.
Meanwhile Daley, who's governed for 22 years with nary a defeat so large as this, may find the city's aldermen more obstreperous than usual.
He's has had a rocky year, from Chicagoans upset with expensive parking meters to worries about city layoffs. Then, in the final bid process days, the video of the brutal beating of a Chicago high school honor student.
In Chicago, thousands of people cast their eyes downward in Daley Plaza, where news of the defeat was broadcast on several large video screens.
"It's their loss," said one woman who only gave her name as Ashley. "We would have made a great host."
Another dejected rally attendee, a local student, echoed her sentiment and added "failure is always a lesson."
Chicago has never hosted an Olympiad, despite winning the privilege for the 1904 games. Those games were relinquished to St. Louis in deference to the Gateway City's Louisiana Purchase Exhibition.
Chicagoans seemed at once resigned and incredulous. The city has harbored high hopes but modest expectations, with many spectators hoping their delegation's star power -- Obama, the First Lady, and Oprah -- would win the day.
Each city's presentation highlighted its particular strengths.
Tokyo touted its eco-friendly plans to host a "carbon-minus" games.
Tokyo was followed by Rio, which argued for the first-ever South American games, and tried to assure delegates that the city was ready to play host to the world.
Chicago, which went first, touted its spectacular lakefront game plan and intra-urban centricity. Obama made an emotional but reasoned plea to bring the Olympics to his adopted home, calling Chicago "the most American of American cities."
But in the end, Obama's accolades weren't enough.