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I think a lot of that would depend on the offset of the wheels you're looking at. Shove the wheel out and the wider cross section of that size tire may create some interference with your fender opening. You also need to consider your vehicle raising and lowering itself with the Quadra-Lift air suspension.
 

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A 285/70R17 would be about 2.25" larger in overall diameter than the original tire. Generally speaking you can usually get away with an increase in overall diameter of 1" without modifications but any more than that and you'll have some work to do. A better 17" size to consider with your stock suspension would be a 265/70R17. This size is just over 1" taller than the factory tire.

As far as wheels go, 17" wheels with the correct offset and width should fit fine. Here's what our system says to look for in terms of width and offset ranges. These ranges will keep the wheel and tire within the wheel wells. Offsets lower than these ranges will push your wheels and tires out beyond your fenders. Offsets higher than these can cause interference with the suspension components and/or unibody.

2014 Grand Cherokee Overland
WIDTH OFFSETS
7 +15/+65
7.5 +22/+65
8.0 +28/+65
8.5 +34/+65
9.0 +41/+65
9.5 +47/+63
 

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If you use a 1.25" wheel spacer you can put factory JK rubicon wheels/tires on the grand. It is very close to the body and I don't care for the look, but it will fit.
 
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