1970 Chevrolet Chevelle SS Convertible – $360,000
Another car that is increasingly expensive to own is the 1970 Chevrolet Chevelle SS Convertible. This car was the pinnacle of the GM performance lineup back in the day. The Chevelle itself was legendary, but the open-air feeling of a convertible only added to the fun. The unique driving experience and the powerful V8 engine are not to be underestimated (via Motor Trend).

The 1970 Chevrolet Chevelle SS Convertible has been fetching more and more money as time has gone on. The car will set you back a pretty penny, and it is one of the rarest models on the road. There are very few cars that could compete with the 1970 Chevrolet Chevelle SS Convertible on a performance level.