This august 14th Im going on vacation and Im taking a b737-900, What are the possibilitys that Ill get 1 with winglets? 
You mean you’re NOT flying a 737-800? Which means you’re NOT flying American?? TRAITOR!!!
Actually, I’d say your chances are pretty good that you’ll have winglets. Every -900 I’ve ever seen here (Alaska & Continental) has had them.
Well its not my fault I dont pick the airline im going in