I lifted up the hood, looked around and became a little sad...where's the trans dipstick?

No dipstick for the trans. It's a sealed unit and FCA does not want people messing with it. There is no maintenance interval. Heavy duty usage might require fluid change at some point, to be done by the dealer. However, a kit can be purchased, make sure you follow the procedure closely.

 

And if you are an export user it seems there suddenly is maintenance interval for some bizarre reason! The Aussie manual states 100,000 km fluid changes.... but still no disptick..

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The Cherokee has Lifetime fluid which I personally consider to be 10 years/100,000 miles. But again thats my opinion.
Unless you trailer tow or off road you really do not have to concern yourself with the transmission fluid unless you notice leakage.
Actually checking the level, assuming you got your hands on a service dip stick, is not recomended, only because doing that function it then becomes possible to introduce contaminents into the fluid.
I trailer tow at under 2,000 lbs and only a boat. Therefore I would guess if I change early it would be around 60k based on what I tow and how much.
Even my wife's '04 Chev. had lifetime fluid. Still I had it changed at 11 years to be safe.
My prior Jeep had a severe maintenance schedule only because it towed. Because of what and how much I towed I could stretch that mileage/time out a bit. Never had a problem. :smile: