I have a 2003 Grand Cherokee I tow behind a 2015 Vegas.
Use Blue Ox and SMI Stay n Play.
went to Alaska and back to Florida (13,500 miles) in 2015 without any problems.
Also, I don't know what year your Cherokee is, but if it is a newer one, make sure it has all the updates for the computers. One of the other's on the tour had a new Cherokee that locked up while being towed. The Jeep dealer in Anchorage fixed it by updating the computer.
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