Methods, systems and media for facilitating compression over a metered data connection are provided. In some embodiments, the methods comprise: detecting a new wireless network connection; determining that the new connection is metered; sending, via a proxy server, requests for content to a content server using the metered data connection; receiving, via the proxy server, content from the content server compressed by the proxy server using the metered data connection; detecting a second new wireless network connection; determining that the second new wireless network connection is not a metered data connection; causing the proxy server to inhibit compression of content sent to the user device in response to determining that the second new wireless network connection is not a metered data connection.