Key West

$88+ Cheap flights from Connecticut to Key West (EYW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — EYW
Jun 18 — Jun 251
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Cheap flight deals from Connecticut to Key West

Cheapest flights from Connecticut to Key West
Explore the most affordable flight options available from Connecticut to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:25 am
BDL
-
EYW
1 stop5h 06m
Breeze Airways
Fri 8/281:11 pm
EYW
-
BDL
1 stop4h 44m
Breeze Airways
Deal found 5/16$166
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BDL
-
EYW
1 stop5h 06m
Breeze Airways
Tue 6/91:14 pm
EYW
-
BDL
1 stop27h 16m
Breeze Airways
Deal found 5/16$223
This Breeze Airways deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:25 am
BDL
-
EYW
1 stop5h 06m
Breeze Airways
Thu 6/412:05 pm
EYW
-
BDL
2 stops11h 06m
Breeze Airways
Deal found 5/19$226
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:25 am
BDL
-
EYW
1 stop5h 06m
Multiple Airlines
Thu 6/412:05 pm
EYW
-
BDL
1 stop28h 40m
Multiple Airlines
Deal found 5/17$235
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:55 am
EWR
-
EYW
1 stop23h 10m
Allegiant Air
Fri 7/2410:31 am
EYW
-
EWR
1 stop22h 34m
Allegiant Air
Deal found 5/18$238
This Breeze Airways deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:25 am
BDL
-
EYW
1 stop5h 06m
Breeze Airways
Mon 6/812:07 pm
EYW
-
BDL
2 stops29h 20m
Breeze Airways
Deal found 5/18$238
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:10 am
BDL
-
EYW
2 stops26h 56m
Breeze Airways
Tue 9/11:14 pm
EYW
-
BDL
1 stop27h 16m
Breeze Airways
Deal found 5/15$239
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:30 am
PVD
-
EYW
1 stop4h 57m
Breeze Airways
Wed 5/2711:46 am
EYW
-
PVD
1 stop11h 11m
Breeze Airways
Deal found 5/16$244
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:05 am
PVD
-
EYW
1 stop6h 26m
Breeze Airways
Thu 8/2712:05 pm
EYW
-
PVD
1 stop4h 53m
Breeze Airways
Deal found 5/16$248
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:30 am
EWR
-
EYW
1 stop22h 49m
Multiple Airlines
Fri 9/2510:59 am
EYW
-
EWR
1 stop23h 28m
Multiple Airlines
Deal found 5/19$265
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:30 am
PVD
-
EYW
1 stop4h 57m
Breeze Airways
Thu 7/3012:05 pm
EYW
-
PVD
1 stop4h 53m
Breeze Airways
Deal found 5/19$268
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:00 am
EWR
-
EYW
1 stop7h 21m
Multiple Airlines
Mon 9/1410:59 am
EYW
-
EWR
1 stop23h 28m
Multiple Airlines
Deal found 5/15$269

Find flight deals from Connecticut to Key West

Keep the following information in mind while searching for Connecticut to Key West flight deals. Data was last updated May 19, 2026.

Round-trip from

$166
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$395
From Connecticut to Key West
One-way flight from Connecticut to Key West
Highest demand for flights based on searches. 15% potential increase in price ($80 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in May 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 19, 2026.
Use the filters below to find and compare flights from Connecticut to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 6/1

7:25 am-12:31 pm

1 stop5h 06m

Key West

Thu 6/4

12:05 pm-11:11 pm

2 stops11h 06m

$226

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 6/3

6:00 am-11:06 am

1 stop5h 06m

Key West

Tue 6/9

1:14 pm-4:30 pm

1 stop27h 16m

$236

ProvidenceKey West

PVD - EYW

PVDEYW

Providence-TFGreen

Sun 8/23

6:15 am-10:27 am

1 stop28h 12m

Key West

Sun 8/30

7:53 pm-1:06 pm

1 stop17h 13m

$302

ProvidenceKey West

PVD - EYW

PVDEYW

Providence-TFGreen

Fri 8/21

1:38 pm-7:54 pm

1 stop6h 16m

Key West

Fri 8/28

6:15 pm-11:59 pm

1 stop5h 44m

$337

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 5/25

7:25 am-12:31 pm

1 stop5h 06m

Key West

Thu 5/28

12:05 pm-11:11 pm

2 stops11h 06m

$343

ProvidenceKey West

PVD - EYW

PVDEYW

Providence-TFGreen

Sun 9/20

4:42 pm-12:19 pm

1 stop19h 37m

Key West

Thu 9/24

12:01 pm-11:40 pm

1 stop11h 39m

$355

ProvidenceKey West

PVD - EYW

PVDEYW

Providence-TFGreen

Thu 9/10

1:33 pm-7:45 pm

1 stop6h 12m

Key West

Sun 9/13

6:00 pm-11:41 pm

1 stop5h 41m

$356

New YorkKey West

LGA - EYW

LGAEYW

New York LaGuardia

Sat 8/15

12:00 pm-7:54 pm

1 stop7h 54m

Key West

Sat 8/22

1:31 pm-9:28 pm

1 stop7h 57m

$357

NewarkKey West

EWR - EYW

EWREYW

Newark

Sat 9/26

6:00 am-10:58 am

1 stop4h 58m

Key West

Sat 10/3

2:35 pm-8:54 pm

1 stop6h 19m

$359

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sun 8/9

6:20 am-10:27 am

1 stop28h 07m

Key West

Sun 8/16

7:53 pm-5:55 pm

1 stop22h 02m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Connecticut to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Connecticut with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Connecticut to Key West

What is the cheapest month to book a flight from Connecticut to Key West?

Currently, December is the cheapest month in which you can book a flight from Connecticut to Key West (average of $132). Flying from Connecticut to Key West in November is currently the most expensive (average of $315). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Connecticut to Key West?

How far ahead should I book a flight from Connecticut to Key West?

The best time to book flights from Connecticut to Key West is 70 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Key West from Connecticut?

    If you book a flight to Key West from Connecticut, you will be flying to Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West.

  • How long is the flight from Connecticut to Key West?

    For as low as $226, Breeze Airways can have you in Key West from Connecticut in 5h 06m. Airlines will cover a distance of 1308 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Connecticut to Key West one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $96. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Connecticut to Key West for a low price.

  • What are the most popular routes from Connecticut to Key West?

  • Can I find deals for flights from Connecticut to Key West that include hotel bookings?

    Yes. In addition to deals on Connecticut to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Key West.

  • Can I find deals for business class flights from Connecticut to Key West?

    Yes. Cheapflights offers flight deals from Connecticut to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to Key West?

    Currently, December is the cheapest month in which you can book a flight from Connecticut to Key West (average of $132). Flying from Connecticut to Key West in November is currently the most expensive (average of $315). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Connecticut to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Connecticut to Key West

Discover the top 5 airlines that operate flights from Connecticut to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$153Average$214FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$172Average$314FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$268Average$442FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$282Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$452FlexibilityNo cancel feeOn-time69%

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