More than 150 politicians and peers have written to the prime minister calling on him to stop the deportation of 50 people to Jamaica.
The Home Office says those being deported are criminals but campaigners say some were as young as 13 when they moved to the UK.
Nottingham East Labour MP Nadia Whittome organised the letter and said deportations should be stopped until a report into the Windrush controversy is released.
She said: “The fact is that many of the individuals in question have lived in the UK since they were children and at least 41 British children are now at risk of losing their fathers through this charter flight.
“The government risks repeating the mistakes of the Windrush scandal unless it cancels this flight and others like it until the Windrush Lessons Learned Review has been published and its recommendations implemented.”
The Windrush generation were named after the ship that brought migrants to the UK from the Caribbean in 1948.
Commonwealth citizens who arrived in the UK before 1973 were automatically granted indefinite leave to remain but many of them were not given any documents to confirm their status.
In recent years, some have been denied access to services, held in detention or removed, despite living legally in the country for decades.
Reacting to Ms Whittome’s request last week, Boris Johnson said: “The people of this country will think it right to send back foreign national offenders.”
Labour shadow immigration minister Bell Ribeiro-Addy said: “Mass deportation by charter flight is the most brutal and inhumane way to remove people from this country.
“It often lacks due process, has little regard for deportees safety, and even less for their right to a family life.
“After the Windrush scandal, we expect better.
“But this government will stop at nothing to maintain its hostile environment.”
Two of the young men set to be deported were convicted of drugs offences as teenager and say they have no link to Jamaica, having left the country at a young age.
Tajay Thompson was convicted of possessing Class A drugs with intent to supply as a 17-year-old.
He served half of a 15-month sentence in 2015 and, now 23, he said: “It’s not like I’m a rapist or a murderer, I’ve made a mistake when I was 17 and it’s now going to affect my whole life.”
Mr Thompson was brought to the UK as a five-year-old and lives with his mother and younger brother in south London.
He has only been to Jamaica twice on holiday since and said: “I feel like I was born here. Jamaica is not my country.”
Akiva Heaven, 22, who served around four years for a drugs offence and was released in May 2018, said: “I’ve done my sentence already, I’ve done my crime, done my time as they would say.
“Now, I’m getting a double punishment.”
Mr Heaven said he fears for his life if he is forced to return to a place where he has no relatives and no memories.
Last year, 29 convicted criminals were deported to Jamaica on the first deportation flight since the Windrush scandal.
The Home Office previously said that under the UK Borders Act 2007, a deportation order must be made where a foreign national has been convicted of an offence and received a custodial sentence of 12 months or more.
Possible exceptions include where this would breach human rights or the UK’s obligations under the Refugee Convention.
A Home Office spokesman has previously said: “The planned charter flight to Jamaica is specifically for removing foreign criminals.
“Those detained for removal include people convicted of manslaughter, rape, violent crime and dealing Class-A drugs.”