The best way to ease the blistering pain of saying goodbye to summer? Start making plans to get out of town immediately.
Luckily, Emirates is offering flights starting at just $999 roundtrip for two people to fly Economy to Milan, Italy this winter ($3,800 for two in Business Class) -- which is pretty hard for anyone to argue with. Flights are from New York (JFK) to Milan (MXP), and must be completed between October 1st, 2015 and March 23rd, 2016. Those who reside outside of New York can connect via JetBlue to JFK, and then go on to Milan on Emirates. And to get the $999 price, tickets must be booked together.
Naturally, there are some blackout periods (which you can check out here, along with more detailed flight info), but overall, a cheap flight for two to Milan is a pretty great way to make up for the fact that you missed your anniversary last month and keep forgetting to pick up toilet paper.