$248 Cheap Flights from New Haven (HVN) to Key West (EYW)

View $248 flight on Sun, Nov 16, 2025Opens in a new window

Popular airlines from New Haven, CT (HVN-Tweed - New Haven Regional) to Key West Intl. Airport (EYW)

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Cheap Flights from New Haven to Key West (HVN-EYW)

Prices were available within the past 7 days and start at $248 for one-way flights and $478 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Sun, Dec 14 - Thu, Dec 18
HVN
New Haven
EYW
Key West
$478 Roundtrip, found 3 hours ago
$478
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sun, Dec 14 from New Haven to Key West, returning Thu, Dec 18, priced at $478 found 3 hours ago
Breeze Airways
Sun, Mar 8 - Thu, Mar 19
HVN
New Haven
EYW
Key West
$487 Roundtrip, found 5 hours ago
$487
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sun, Mar 8 from New Haven to Key West, returning Thu, Mar 19, priced at $487 found 5 hours ago
Breeze Airways
Sun, Dec 14 - Fri, Dec 19
HVN
New Haven
EYW
Key West
$492 Roundtrip, found 3 hours ago
$492
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sun, Dec 14 from New Haven to Key West, returning Fri, Dec 19, priced at $492 found 3 hours ago
Breeze Airways
Thu, Mar 12 - Mon, Mar 23
HVN
New Haven
EYW
Key West
$497 Roundtrip, found 5 hours ago
$497
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Mar 12 from New Haven to Key West, returning Mon, Mar 23, priced at $497 found 5 hours ago
Breeze Airways
Thu, Dec 11 - Fri, Dec 12
HVN
New Haven
EYW
Key West
$501 Roundtrip, found 1 day ago
$501
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 11 from New Haven to Key West, returning Fri, Dec 12, priced at $501 found 1 day ago
Breeze Airways
Thu, Mar 12 - Thu, Mar 19
HVN
New Haven
EYW
Key West
$506 Roundtrip, found 5 hours ago
$506
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Mar 12 from New Haven to Key West, returning Thu, Mar 19, priced at $506 found 5 hours ago
Breeze Airways
Thu, Dec 18 - Mon, Dec 29
HVN
New Haven
EYW
Key West
$511 Roundtrip, found 3 days ago
$511
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Dec 18 from New Haven to Key West, returning Mon, Dec 29, priced at $511 found 3 days ago
Breeze Airways
Sun, Mar 15 - Thu, Mar 19
HVN
New Haven
EYW
Key West
$515 Roundtrip, found 5 hours ago
$515
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sun, Mar 15 from New Haven to Key West, returning Thu, Mar 19, priced at $515 found 5 hours ago
Breeze Airways
Sun, Nov 9 - Thu, Nov 27
HVN
New Haven
EYW
Key West
$517 Roundtrip, found 5 days ago
$517
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Nov 9 from New Haven to Key West, returning Thu, Nov 27, priced at $517 found 5 days ago
Breeze Airways
Thu, Dec 4 - Thu, Dec 18
HVN
New Haven
EYW
Key West
$519 Roundtrip, found 21 hours ago
$519
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Thu, Dec 4 from New Haven to Key West, returning Thu, Dec 18, priced at $519 found 21 hours ago

Alternative airports near Key West

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Key West Intl. EYW. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $517
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $517

Frequently asked questions

How much does a flight from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW) cost?
Lock in a cheap one-way flight from $248 or cheap return flight from $478 from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW)?
The cheapest month to fly from HVN to EYW is December, when there's less demand. Off-peak season is often when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW)?
To find the cheapest airline flying from HVN to EYW, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW)?
You'll have to take a flight with a layover when traveling from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from HVN to EYW?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW)?
To reach Key West Intl. Airport (EYW) without delays, book a flight that leaves from Tweed - New Haven Regional Airport (HVN) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW) last-minute?
Last-minute fares from HVN to EYW are generally more expensive. To secure the lowest prices, start searching for flights early. That said, if you can play around with your travel dates, it's possible to land a cheap ticket just before your departure.
Is it cheaper to book a HVN to EYW flight and hotel package?
Compared with arranging flights and hotels separately, booking a HVN to EYW flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one place will take the stress out of travel planning. Just pick your flights and select from our wide range of stays, then customize your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Tweed - New Haven Regional Airport (HVN) to Key West Intl. Airport (EYW)?
If you booked your HVN to EYW flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Origin airport
Tweed - New Haven Regional
Destination airport
Key West Intl.
Airlines serving
Breeze Airways
Roundtrip price
$478
Distance
1262 mi

Book with confidence

New Haven to Key West Flights

The cheapest times to fly from New Haven to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from New Haven to Key West are during the month of December. You can find some of the cheapest flights from New Haven to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from New Haven to Key West

Sunday is one of the best days to book for cheap flights from New Haven to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from New Haven to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from New Haven to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $248 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap New Haven to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your New Haven to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

New Haven to Key West Flights

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*Available to One Key members.