Daniel Leeson won the getaway during a gig for the LGBT organisation which took place onboard a tram from Chorlton to Manchester airport.
The concert was supported by Thomas Cook Airlines and Manchester airport and saw 90 guests riding the tram while being entertained by singer Shane Richie Jr, drag queen Belinda Scandal and DJ Greg Thorpe.
Thomas Cook Airlines and Manchester airport are the official sponsors of Manchester Pride’s The Big Weekend – taking place in the city over the August bank holiday.
Upon winning his trip Leeson said: “I honestly couldn’t believe that I had won when they scanned my ticket. My first thought was work of course but my manager at Manchester City Council has been amazing. She gave me the time off right away and I couldn’t be more grateful to her and my colleagues.”
Commercial director at Manchester airport, Stephen Turner, added: "It was a great event and showcased a range of partners coming together to support such a worthy cause. Everyone at Manchester airport hopes Daniel has an excellent trip to Boston with Thomas Cook Airlines and enjoys all this great city has to offer to tourists and holidaymakers."
Sharon Confue, head of sales for UK and Ireland at Thomas Cook Airlines, said: "We really value the opportunity that The Big Weekend and its warm up events offer for us to continue to build our reputation as the biggest long-haul carrier outside of Manchester airport. It’s great that individuals like Daniel can benefit with such amazing prizes along the way, as well as our cabin crew and retail staff experiencing unique events and flying to amazing destinations."
Chief executive for Manchester Pride, Mark Fletcher, added: “Boston is a brilliant city and Daniel is set for quite a weekend.”