NFL Network Insider Ian Rapoport reported the Bears had a "positive meeting" with Jeffery's agent Saturday and that both sides are "more than open to a reunion."
Just this week, Antonio Brown became the highest-paid wide receiver in the NFL when he signed a four-year extension that moves his per-year average to $17 million. Jeffery will be looking to exceed that number with his next deal.
Jeffery has said that he wants to sign with a contender, explaining Thursday, "Whatever the next chapter is, I'm ready for it. I'm looking at the teams that obviously need a wide receiver, but also put me in the best situation to win a championship right now."
The Bears, who are coming off a 3-13 season and have major questions at quarterback and other positions, are not contenders.
But, with enough positive meetings and lucrative offers, they could change Jeffery's mind.