If cookies are made with enough sugar, will they just be chewy caramel?

There are no similarities between the process of making caramel and making cookies.

Pure caramel has one ingredient, sugar. This sugar is cooked on the stove and brought to a high temperature until it changes color.

The process of caramelization consists of heating sugar slowly to around 340 °F (170 °C). As the sugar heats, the molecules break down and re-form into compounds with a characteristic color and flavor.

There are two products you may be talking about instead that are called caramel - caramel sauce and caramels, or milk caramels, a wrapped candy product.

Both of these are made in a similar fashion - heat sugar and other ingredients on the stove to a specific temperature point. These added ingredients include corn syrup, cream/half & half/milk, and butter.

While these ingredients share similarities to some degree with cookies, cookies rarely ever include liquids like milk as you need to keep the dough thick so that it doesn't spread, and will always include some sort of flour and (usually) eggs, which are not a standard ingredients in caramel recipes (and probably never ingredients).

The process for cooking is similar to pure caramel, they are cooked in a saucepan on the stove until they reach a specific temperature, something around 250F. At this temperature, the chocolate chips would be completely melted.

You can certainly make chocolate caramels, if that is what you wish, but you could not convert a recipe for chocolate chip cookies to a caramel recipe.

Adding more sugar to the cookies would make them spread quite a bit more (remember that sugar is considered a liquid in baking cookies) and eventually you'd get something like a lace cookie, which is probably the closest you'd ever get to caramel in a cookie recipe. Lace cookies contain flour but significantly less flour than sugar.

As an example, this recipe for Oatmeal Lace Cookies has only 3 tbsp of flour (and 2-1/4 c oats) but has a whopping 2-1/4 cup of sugar along with two sticks of butter. The method is also similar to caramel, in that it's a boiled batter that is heated in a pot on the stove and then baked.

This is probably the closest crossover you're going to get between the two. And, as a bonus, if you want chocolate, lace cookies are often dipped in or drizzled with chocolate.

Honey-Almond Lace Cookies from Food Network:

Yes and no.

There isn't a point at which they will ever be pure caramel - the flour would alter the texture enough to prevent it from being "pure", not to mention the chocolate would burn before that point.

It is possible to have enough sugar in the cookies that it can become caramelized, but this would happen with very flat cookies, in a thin batter, being cooked at high temperatures - you can see this with brandy snaps, or Florentines, or whatever else this style of cookie may be called.

Cookies made this way have a pitted, crunchy texture, and are extremely brittle. They are thin because the sugar has to melt and run before it gets to the heat where it caramelizes and sets - a cookie intended to be thicker might only caramelize on the bottom, or run all over the place when the sugar melts, or somehow otherwise not cook properly. The temperature won't get high enough to caramelize the sugar without drying all the water out of the cookie. The pitted texture is from the bubbling that takes place, because the caramel will set hard and preserve this texture.

And, again, any chocolate chips will melt, and burn, long before the sugar caramelizes. Your cookies might withstand a local caramelization, browning on the top or bottom - but often the chocolate chips on the surface of well browned cookies are hard and dry, so I don't think this kind of cookie will do better. You might sprinkle a few choc chips on a Florentine as it comes out of the oven, and let them melt with the residual heat. Or you might make some other filling (usually Florentine are paired a creamy filling, look at brandy snaps, so perhaps a cookie-dough-dip filling would work well)

As others have pointed out you won't get "caramel". What you do get can be pretty good though.

I once messed up a cookie recipe by copying it down wrong. I inverted the sugar and Flour. I added 3/4 cup of flour and 1 1/4 cup of sugar. Followed the rest of the recipe exactly.

Now what come out of the oven, was neither cookie or "caramel". It was like a super chewy, gooie wad of sugar goodness. They had to be stored individually (or they would stick together) and they pulled apart a bit like warm silly putty, but we chilled them in the fridge for a few hours and they made really good "candies".

The chocolate chips had melted into the "candies" pretty well but they were still distinct.

The flavor was not "caramel" though. It was more like eating raw cookie dough, except that it had that finished cookie taste. Obviously they were very sweet, but it still tasted like a cookie.

Go ahead and try it. Worse case you loose the ingredients.