Resentment and anger has brewed among thuggish far-right groups and powerful clerics who treat homosexuals with disdain.
Weighed down by a restrictive Soviet heritage but filled with lofty European aspirations, the crisis-torn east European country hopes to use the global spotlight to showcase its tolerance of values long-cherished in the West.
Yet beneath the liberal facade put on by the city, which wants fans at Saturday's final to celebrate "our unique differences," resentment and anger has brewed among thuggish far-right groups and powerful clerics who treat homosexuals with disdain.
And while the Kyiv Pride LGBT rights group distributes maps of gay-friendly places tucked in the shadow of Orthodox churches, beatings of homosexuals are routine and even the prime minister shudders at the thought of legalising same-sex marriage.
"God forbid!" Volodymyr Groysman exclaimed in November 2015. "We will never support this."
The most vivid display of Kiev's embrace of diversity involved plastering a giant arch in the heart of the city that symbolised the Soviet-era bond between Ukraine and Russia with the rainbow colours of the LGBT flag.
Ukraine has wanted to distinguish itself starkly from it arch-foe Russia, its eastern neighbour that has drawn global condemnation over crackdowns against the LGBT community.
Soaring 35 metres (115 feet) above the Dnipro River, Kiev said the arch would become the world's largest artificial rainbow.
Ultranationalist group Right Sektor has actively resisted the initiative.
The arch is now a jarring sight: part rainbow, part shiny grey metal, the city halted work on the project when confronted by hostile Right Sektor activists waving their ominous red and black banners.
"Kiev is not the European capital of gays," Right Sektor spokesman Artem Skoropadskiy told AFP.
Father Feodosiy of the dominant Ukrainian Orthodox Church warned that Kiev's rainbow arch could jeopardise the country's entire social value system.
"There will be inevitable consequences for the entire nation if this ideology and these sins are spread everywhere with the help of such an enormous symbol," he told AFP.
But Ukrainians like Zoryan Kis, a gay LGBT activist, called the nearly-completed rainbow arch a "perfect metaphor of 'celebrating diversity' in Ukraine".
"It basically shows that diversity is not fully achieved in Ukraine, but that we are almost there," the 34-year-old said on an optimistic note.
International rights groups have praised Ukraine for having recently introduced legislation that offers the LGBT community more protection.
Ukraine banned sexual discrimination in employment in 2015 after having been pressured by the European Union, which it has been trying to join.
But Human Rights Watch noted in 2017 that "anti-LGBT sentiment remains strong among high-level government officials and the public" in Ukraine.
Despite extra security measures taken ahead of the contest, Ukraine's social media world was shaken by the violent beating of a lesbian woman earlier this month.
Kiev resident Gala Korniyenko, 40, and her girlfriend Nataliya went fishing in the countryside and ran into a group of rowdy men who were having an alcohol-fuelled party.
When one of them learned that Nataliya was a lesbian, he pushed her to the ground and began kicking her as the others watched.
"He was screaming that he'll kill her and bury her and people like her should not exist," Korniyenko told AFP.
Nataliya suffered a concussion, but Korniyenko said there were still signs that the times were changing because the attack received broad attention and that the LGBT community was no longer afraid of speaking out.
"Two years ago we would have swallowed it," Korniyenko said.
Nevertheless, activist Kis urged gay and lesbian couples who come to Kiev for the 42-nation song contest to keep their displays of affection private.
"Ninety-five percent of the people would react normally, but there is always a risk that you will come across a crazy far-right teenager," Kis cautioned.