The 31 year old is available on a free transfer after seeing out his contract at Stoke earlier this summer.
Boro boss Tony Mowbray has held talks with former Sunderland captain Whitehead and hopes he can persuade him to move to The Riverside.
"I feel he could help solidify us out of possession," Mowbray told the Evening Gazette.
"Can we do it? I think the boy has got options but he's somebody we've talked to and we'll see what develops over the next few weeks."