Hello, I'm Darin. I know, you were hoping to find a web site that listed the cheapest available flight from your location to Key West. Unfortunately, that kind of web site doesn't yet exist. There are some that come close, but they only provide flight options from a few connected airlines.
Don't despair just yet. The content I have put together here should help you minimize your search time and zero in on most Key West cheap flights. These tips and tricks can be found in various places around the web. I just brought them together for your convenience.
The beauty of these tips is that they can apply to any location you are interested in, so although I am using Key West as my example here, you can substitute any city of your choice and simply follow the same process.
Finding cheap flights requires some work as I mentioned above, but how do you know when you have truly found a cheap flight and not just a price that seems to be the lowest of the ones that you are seeing?

The first thing you need to do is to establish a base price. This would be the average price that most airlines and travel agencies are charging on the days that you want to travel (to and from).
If you are searching months ahead of your planned travel dates, then the prices you are looking at are most likely already discounted. To set your base price you need to look at prices for flights that are no more than two weeks from the date you are searching. This would be a better approximation of the normal flight costs.
Make sure that you have researched at least three local travel agencies, three online travel agencies and three airline web sites that offer travel to Key West.
Please note that as Key West is a small island with a small airport, most flights that you find will have a U.S. stop over, typically in Miami. Unless you are flying from a location in the Eastern U.S., you will not likely find any direct flights.
Great, now you have a base price to work from. This will help you get a much better feel for Key West cheap flights compared to regular priced flights. If you end up finding something that is 50% of this base price, then you have truly done well.
The very first place to look is for package deals. These package deals come in various forms, so you will need to check each one out to see what may be available.
Often when we use the term "flight package deal", we are talking about vacation packages. After all, Key West is a tourist destination for fun and sun. If you were planning to stay in Key West for any length of time, whether you were looking for a single destination spot or just a place to use as a base for your excursions, often an all inclusive hotel package can offer the cheapest overall costs.
Key West is a small island, so most hotels will offer everything you are hoping for. One way to look for cheap flights is to look at it from the hotel perspective. Quite often hotels will subsidize airlines as long as the traveler ends up at their hotel.
Looking for Key West cheap flights in this manner requires that you are quite flexible as to your hotel destination and the airline that takes you to Key West (requires changing airlines at a connecting location). The cheapest flight and hotel combinations are often found this way, so you may need to consider giving up on the absolute cheapest price, to get a better hotel.
When using this approach you will need to do extensive research on the potential hotels to make sure you find the best combination to suit your needs.
This is one technique that very few people utilize, and yet it can result in significant price reductions. We know that the vast majority of flights to Key West will require a stop over somewhere, so what difference is it to you where that stop over occurs (as long as it doesn't extend your trip duration by too much)?
Most flights to Key West will stop over in Miami, however there are a few other Florida airports with direct flights to Key West.
Tampa
Fort Myers
Fort Lauderdale
You should do some research to see whether a stop over in these other Florida locations might offer reduced prices.
The biggest opportunity for Key West cheap flights is found in stop overs at U.S. eastern hub airports. Direct flights to Key West from these hub airports are often cheaper because these airports are designed to maximize passenger volumes on each outgoing flight. The more passengers on average, the cheaper the cost per passenger.
The other important advantage is that flights from your home location to these hub airports are often cheaper as well.
Two of these large hub airports are the Charlotte, South Carolina airport and the Atlanta, Georgia airport.
Don't be afraid to change airlines at these hub airports. Take a major airline to the hub airport and then a commuter flight to Key West.
Several techniques for finding Key West cheap flights have been outlined above, let's summarize.
First use our techniques for setting the base price so that you can be certain that you have found a flight combination that can truly be categorized as cheap. Remember that the lowest price shown at a travel agency doesn't necessarily qualify as a cheap price. It could easily be the lowest of the most costly fares.
Next you need to check out vacation packages and hotel subsidized packages. When using this technique you need to analyze your total trip costs to see whether the savings are worthwhile. Remember that Key West is a small island, so most hotel locations will be fine.
Stop over locations are next on your research list. Search for flights from your home airport to these other specified locations in Florida or eastern hub airports. Then check the costs of the flights from these locations to Key West. Add up the total flight costs to find the winner.
To find your Key West cheap flights you must remember that flexibility on your part can have significant rewards in regards to price reductions. Here are a few of the areas where flexibility must be considered
extending your travel days to a few days on either side of your initial planned travel days
book early or try for the last minute deals
find commuter flights where possible
book each way separately
book on low travel days
check the airfares directly with each airline
I hope these tips and tricks help you find Key West cheap flights from your home location wherever it may be.