The Grand Cherokee starts thousands higher than rivals such as the Kia Telluride and the Hyundai Palisade —consider it the Jeep-brand tax—and its higher trims are priced similarly to some luxury SUVs.

All Grand Highlanders come with a suite of driver-assistance features that Toyota calls Safety Sense 3.0. In addition to basics such as blind-spot monitoring and automated emergency braking, the ...