In a television interview with Britain's Sky News, he said al Qaeda's ideology was one of total antagonism toward democracy and other religions.
"Nobody wants to negotiate their own demise or their own surrender, so it strikes me as a kind of academic exercise," he said.
Chertoff was responding to a question about Northern Ireland police chief Hugh Orde who told Britain's Guardian newspaper last week that lawmakers should consider negotiating with al Qaeda.
Chertoff told Sky interviewer Rachel Younger he did not believe that such talks were possible.
"Their (al Qaeda's) interest is in the destruction of the West, and unless you are prepared to negotiate about how you want to be destroyed, it strikes me as a totally speculative and unrealistic exercise," he said.
He said that al Qaeda has grown stronger in Pakistan and Afghanistan in the past year but has weakened in Iraq.
Chertoff also said he believed Europe was still a target for terrorist attacks and people should be vigilant during the summer months.
"I think if you look back historically, those who are interested in carrying out terror attacks look for periods of time when there is a lot of travel, people are moving around a lot, that creates extra vulnerability in our rail systems, in our aviation systems," he said.
He stressed, however, that he was not aware of any specific plot.