A gaming machine with interactive pop-up windows providing enhanced game play schemes, including side-bet schemes, is described herein. Placing a side-bet utilizing interactive pop-up windows enables the player to make an additional wager to "purchase" one of any number of game enhancements, or to "side-bet" that the game outcome will include a particular symbol or symbol combination, depending on the side-bet scheme enabled for a particular gaming machine. In an embodiment, the player has an option to select one or more side-bet(s) via a pop-up window(s) prior to game play initiation. In another embodiment, the player has an option to select one or more side-bet(s) via a pop-up window(s) after a partial game outcome is displayed.