The subject invention is directed to a portable entertainment system that includes a housing unit and an audio system supported by the housing unit. A transport structure is coupled to the housing unit such that the housing unit is portable. The audio system includes electronic audio equipment and at least a first pair of speakers coupled to the electronic audio equipment. The housing unit contains a speaker enclosure and a support panel is disposed between and substantially parallel to the front and rear panels and the support panel divides the speaker enclosure to form a front air-filled section and a rear air-filled section. A first audio port extends through the housing unit into a front air-filled section of the speaker enclosure and a second audio port extends through the housing unit at least into a rear air-filled section of the speaker enclosure. When a first pair of speakers moves towards the rear panel in response to electrical signals from the electronic equipment, compressed air within the rear air-filled section flows out of a second audio port and when the first pair of speakers moves towards the front panel in response to electrical signals from the electronic equipment, compressed air within the front air-filled section flows out of a first audio port.