Cheap flights to
Key West (EYW)

We’re always asked about the best day of the week to book flights, and the truth is: There isn't one. However, there is a timeframe when flights tend to be cheaper. It’s about 1–3 months before a domestic flight and 2–8 months before an international flight. We call this sweet spot the Goldilocks Window because it’s not too far ahead but also not too close to your departure date.

For anyone booking a flight during peak travel season, or if your trip requires specific travel dates rather than flexibility, we recommend planning even further in advance. If, for example, you’re hoping to visit Key West in December, you’d be wise to start looking at fares in July. Last-minute deals are few and far between during busy travel seasons. In fact, we see fare jumps happen pretty regularly at the 21-, 14-, and 7-day points before a trip, so it’s best to book before those dates if at all possible.

One of our favorite tips for getting to the Greek Islands during pricey travel periods is to look for the cheapest flight to another European city—like London, Paris, or Milan—then find a budget airline flight from there. The Greek Islands Trick can work all over the world. Just look for the least expensive flight to get you as close as possible to your destination, then find another mode of transit for your last leg.

To reach Key West, that likely looks like finding a flight to Miami and renting a car. You could also look at other airports in Florida. From Orlando or Miami, you can try to find a cheap flight to Key West or spend a few hours on the road south (which happens to be a pretty drive anyway!) It requires a bit more work and time, but it could save you a bunch of money on a winter Key West getaway.

This is like the Greek Islands Trick but in reverse. If you live in Milwaukee, flights to Key West can be very expensive during peak season. Check for flights out of Chicago instead. Similarly, if you live anywhere in the Northeast, it might be worth searching for flights from New York. The extra drive or train trip isn’t ideal, but it could save you a few hundred bucks and, because you’d likely have to make a layover anyway, it might not even take much more time.

The simplest way to save money on flights is to fly during the off season. In Key West, that’s September to November, which also happens to be a beautiful time to visit. August is also fairly cheap.

The more flexible you can be with your travel dates, the better your chances of finding cheaper flights. Even if you are planning to travel from December to April, the busy season, try playing around with different dates; if you can fly during the week, you’ll likely save money. Tuesdays, Wednesdays and Saturdays are typically the cheapest days to fly, while Fridays and Sundays are the most expensive.

Another easy way to save is to set fare alerts and let technology do the work of searching cheap flights for you. Set up alerts for any specific itinerary you’re looking at, and you’ll get an email when the fare drops into your target price range or by a noteworthy amount. We recommend doing this before the Goldilocks Window we talked about before so you can see the deals during that time. If your dates or departure and arrival airports are flexible, set a few alerts.

Key West is a small airport with direct flights from 11 states and Washington, DC. It’s not the easiest to reach, but it is very close to Miami, which is a large airport with hundreds of flight options from around the US and the world. You can reach Key West from almost anywhere in the US, the Caribbean, or Europe with just one stop.