If your chatbot can be more convincing than three other finalist chatbots over four half hour dual-conversations (a human judge conversing simultaneously with one chatbot and one confederate human, but is not told which is which) then you stand to win a solid bronze medal and $4000 ($1500, $1000 and $500 to the runners-up).
A silver medal and $25,000 goes to any chatbot which fools half the judges.
To get $100,000 and a solid gold silver medal, you'll need to make a chatbot that is indistinguisable from a human over video chat, now that's a proper challenge!