The Bears' next game is at Minnesota on Sunday, and coach Marc Trestman said he expects Cutler to remain sidelined because of a high left ankle sprain.
Chicago then hosts Dallas on Dec. 9. If he's not ready for that Monday night game against the Cowboys, Cutler expects to return at Cleveland on Dec. 15.
"I will be playing either that Monday game or wherever we play after that," Cutler said Monday during his weekly appearance on WMVP-AM 1000 in Chicago. "Let's lean toward the Monday game, though."
Cutler said that he won't need surgery and there's "zero chance" he's finished for the season.
Trestman is also confident that his quarterback will return in December. But Cutler will likely sit out his third straight game when the Bears visit the Vikings.
"I'm totally confident he'll play again this season," Trestman said. "I don't have any reason based on what I've been told. It's still week-to-week. I'm confident. I think Jay is confident. You have to leave yourself an opening, but there is no underlying information here."
As for Cutler, the past month has been a rough one.
Cutler tore his left groin muscle against Washington on Oct. 20 and missed the next game at Green Bay two weeks later. He returned earlier than expected against Detroit on Nov. 10, only to injure his ankle. Josh McCown has played well in his place.
The injuries cast another layer of questions surrounding Cutler's future in Chicago. He has an expiring contract and could be hit with the franchise-player tag after this season.
If that happens, Cutler told the radio station he would be fine with it and that he wants to stay in Chicago.
"I'm not going to take anything personally," Cutler said. "If they want to franchise me, I'm going to feel good about the situation we're in. We're going to be in our second year of the offense with these guys. We're going to be better, I'm going to be better, so it's not personal. It's business."
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