Cutler finished 23-of-39 passing for 292 yards and an interception. His prime target was Brandon Marshall, who hauled down 12 passes for 144 yards and a score.
Matt Forte racked up 107 yards on 22 carries for the Bears (4-1).
The Jaguars (1-4) were led by Blaine Gabbert, who managed just 142 aerial yards and was picked off twice.
Maurice Jones-Drew led Jacksonville rushers with 56 yards on 12 carries.