How to Keep Chocolate Chip Cookies Soft for Days
The solution is more obvious than you might think.
Chocolate chip cookies, especially homemade ones, don't last long in my house. But if by some miracle, a batch of cookies lasts two or even three days, I still want them to taste as soft and chewy as they did when I pulled them out of the oven.
There are two tricks to keeping cookies soft, and they are so simple and obvious you might be doing them already, but hear me out: don't overbake your cookies and store them in an airtight container. That's it! Some folks swear that placing a slice of white bread (or a flour tortilla) in the container with the cookies will keep cookies softer longer. This may be true, but I haven't ever had the need to do it.
And that's because I always pull the cookies out of the oven a minute or two before they are done baking. Most cookie recipes include a range of baking times, like "8 to 10 minutes". I recommend removing the cookies from the oven at the earlier end of that range. They may look slightly underbaked when you do this, but the cookies will continue to firm up on the hot cookie sheets as they rest for a few minutes. Once they have cooled (or if they are still-warm—who can resist chocolate chip cookies at that stage?), they will have a perfectly tender texture that should last for a few days.
The key to the second trick, storing the cookies in an airtight container or ziplock bag, is to make sure the cookies have cooled to room temperature. If you seal the container when the cookies are still warm, steam will get trapped inside the container, which might soften the cookies too much. I prefer using a ziplock bag instead of a food storage container because I can press as much air out of the bag as possible, which also helps prevent stale cookies.