Cheap flights from Hartford to Key West from $140

In general, September is the cheapest month to fly from Hartford to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $345. If you are unable to visit Key West during the month of September, then departing from Hartford during the month June is also very affordable. Most momondo users find prices during this month for around $377.

You are more likely to see cheaper flights to Key West from Hartford when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $479 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Hartford for as low as $438 on momondo.

You could potentially save up to 55% on your flight if you consider stops on a Hartford to Key West flight.

As of October 2026, prices for Hartford to Key West flights are approximately 215% more expensive when compared to flights at the same time last year.

Breeze Airways is the most popular carrier operating from Hartford Bradley Intl to Key West

American Airlines, Breeze Airways and Delta are the top three most popular airlines that fly to Key West from Hartford according to our data. American Airlines is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 4 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.

Tampa (TPA) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

Flights via Miami (MIA) offer the lowest average round-trip price of $769.

Flights connecting via Miami (MIA) have the shortest average one-way travel time: 4h 42m.

Tampa (TPA) has the shortest average layover time for this route: 0h 40m.