chromebook won't download apps?

I am in a pilot program at our school, where were all given Dell chromebooks, and my chromebook recently download apps from the webstore. The school doesn't block the apps I try to download, and the issue is that I will attempt to download an app, It ask permission and I give it consent to download the app. Then it gets stuck on the checking phase. I have literally left this stupid machine running all night and it won't download apps. Help?