This achievement is complete RNG, it may take you 1 attempt, or it may take you 100.
You need to have access to Fort Frolic, and be able to visit Sir Prize Games of Chance where all the machines are located (Shown above). To get the achievement you need to get 3x$ for a $250 reward. I started out with around $100 in my wallet and just saved anytime I went above my initial starting money, and loaded when I ran out.
I spent about 35min to get it, and ended on $490 when I was done. Good luck. I haven't confirmed this, but other gambling machines around the level *may* give you the achevement as well.