Workers from a number of the area's top firms, along with charity workers and members of the public, will be braving a starry night on a cardboard box on Friday from 6pm.
In an attempt to raise awareness and money for the charity Save the Family,
the sponsored sleep out will be taking place on Cathedral ground in Dean's Field.
Ian Oulton, Save the Family chief executive, said: "We felt staging a sleep out would be a perfect opportunity for our supporters to discover for themselves the harsh reality of having nowhere to stay, no roof over their heads, and of being at the mercy of the elements.
"It will be an exciting way to raise money and help families from throughout the area break the vicious cycle of homelessness."
The money raised will go towards the charity's developing Cotton Hall Farm centre on the outskirts of Chester.
The centre is intended to house 26 family units alongside training facilities and a children's centre to help the hundreds of young families throughout the region who are without a home.
With support from Chester's BiG Storage, participants will be provided with cardboard boxes in true homeless fashion.
Andrew Donaldson, of BiG Storage, said: "I believe it is imperative that we do all we can to support Save the Family and I urge people to dig out their sleeping bags and bed down for a good cause."
The programme has also received donations and support from the global foods industry leader, Unilever, which will be providing soup and supplies to those taking part.
Mr Oulton said: "People have been so generous in their support of Save the Family's work and we're extremely grateful.
"The more people we get to participate, the more awareness we can raise about the issue.'
With entertainment, refreshments and toilet facilities being provided, the organisers are urging members of the public to get involved with the first time invent."
For more information contact Gemma Ryder on 01244 333490.
The full article contains 365 words and appears in Evening Leader Chester newspaper.