Amazing Heists: Dillinger is a hidden object game with a plot based on the true story of John Herbert Dillinger, a career criminal that robbed several banks in the early 1930s. As Dillinger and his accomplices, the objective is to search and find all the items from a list at the left side of the screen within a time limit, on banks and other related locations. The time limit is optional and can be turned off at the beginning of the game. One of the list items is a riddle displayed in green about a object, for example “shelled reptile” for a turtle. The hint button highlights the position of one of the required objects. The player receives extra hints after picking up all the five multi-colored keys or the riddle object.

Besides the list objects, there are eighteen bonus items scattered throughout the scenery that can be collected and stored on separate slots. They are nine coins spelling “DILLINGER”, and nine wanted posters. When collected, they give a $5000 cash bonus. Stacks of money and coins can also be clicked for some bonus cash, while safes give extra time.

Most chapters take place on banks, with a few featuring other locations. At the start of each stage, the player has to select two accomplices from the available roster. Each gang member has a different skill, helping the player by giving extra time and speed to finish the mini-games. At the end of each chapter, two mini-games appear that must be solved to complete the robbery. In the first one, the gang members have to be positioned on the bank exits, to stop any bank patron trying escape the premises. In later stages, there are more exits than gang members available, and the player has to keep moving the criminals around to block all the escape routes. The final mini-game is the safe puzzle, where the previously collected keys have to be used on five locks to open the safe door. The correct combination has to be discovered by trial-and-error, with the player memorizing the correct sequences after each mistake.