Trade-in or Sell to 3rd Party?
 

I have a 2008 red Wrangler Unlimted X with 46K miles. I am thinking about getting a new car, but always struggle with whether to sell it on my own or trade it in. The benefits of selling it on my own is that I think I could net an extra $2-$3K, however this will be offset by about $1500 since you don't get the sales tax benefit of trading in a car in Illinois. The benefits of trading it in is that I can truly "walk away" from it and don't have to worry about meeting strangers in parking lots, dealing with cashiers checks, and worrying about whether a major problem will happen one week after they buy the car from me. I also will see what CarMax will offer me too.

KBB (good condition) has my car listed at $21.9K in 3rd party sale and $19.1K in trade-in. What is everyone else's opinion/experience on selling your Wranglers?

I always have had good luck with trading in my Jeeps, you also need to consider the sales tax savings if you live in a state that charges sales tax. For example Texas charges 6.25% every time a vehicle is sold, but when you have a trade they only charge you for the difference of your new vehicle and the trade in value. Which most of the time will out weigh the additional money that you would get selling it outright.