Retirement tax questions

The game show will send you a 1099-MISC.  The 1099-MISC would be entered under "Other Income"  On the main screen, under Federal Taxes, select Wages & Income.  On the next screen you can click "I'll Choose What I work on"

That will take you to the Income Summary screen.  Scroll down and look for "1099-MISC and Other Common Income".  Your prize money should be entered there.  Note that the trip value may be overinflated.

You may wish to make estimated tax payments.