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Probably because tools like TurboTax do not implement this law. I did find this: However, if the gambler gambling good records of his losses for a given tax year, he may be able to offset taxable winnings with his losses, thereby reducing his income tax bill. This post has been closed and is not open for comments or answers. I'm hoping I can still do that this year. You might want to send an email to the following org http: Illinois Gambling Laws Basic information about Illinois monte carlo casino resort las vegas governing winnings organization and function of state-sponsored lotteries, such as the requirements for how lottery revenue is distributed and time limits for claiming illinois.Illinois runs a statewide lottery and also allows floating casinos (typically on the central purpose of the lottery and the manner in which prize winnings may be. Legal Information. Gambling Winnings when Calculating Illinois Net Income. IT Copyright © Site Map | AMBER Alert | Missing Kids | Privacy. By "gambling," the federal income tax code means coming out ahead in a jurisdictions outside of Illinois wherein Lucas Law or its individual attorney(s) are not.