I have both. They each do what the other can't. You really can't replace the Wrangler for being a true jeep. It takes a special breed to drive one which I think is why we all wave to each other as we drive past. I do really also like my Cherokee. It has a lot more room (secure room) tows better and is warmer in the winter. It is also very capable off road.
If you are really looking for practicality, the Cherokee is your best bet. If you want a Jeep, buy a Wrangler. There is nothing else like it.
With the amount of information you've provided, you'd probably be better off throwing a dart at a dartboard.
Do you have a family? Kids? Dogs? Do you do more highway driving than city? How important is taking the top off to you? Do you plan to modify it after the initial purchase? Whats you're budget? How important are the conveniences of the Cherokee? Do you need to tow larger trailers?
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