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Key West

$185+ Cheap flights from Worcester, MA to Key West (ORH - 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — EYW
Mar 21 — Mar 281
Sat 3/21
Sat 3/28
1 adult, Economy
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Cheap flight deals from Worcester to Key West

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

This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/122:39 pm
ORH
-
EYW
2 stops25h 01m
American Airlines
Thu 4/165:42 pm
EYW
-
ORH
1 stop20h 32m
American Airlines
Deal found 2/18$212
This American Airlines deal was found by Cheapflights users on 2/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:39 pm
ORH
-
EYW
2 stops25h 51m
American Airlines
Mon 4/203:58 pm
EYW
-
ORH
2 stops22h 16m
American Airlines
Deal found 2/17$248
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:30 pm
ORH
-
EYW
2 stops23h 45m
American Airlines
Mon 3/97:42 pm
EYW
-
ORH
2 stops17h 37m
American Airlines
Deal found 2/18$257
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:39 pm
ORH
-
EYW
2 stops8h 19m
American Airlines
Fri 4/175:42 pm
EYW
-
ORH
1 stop20h 32m
American Airlines
Deal found 2/18$282
This American Airlines deal was found by Cheapflights users on 2/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:18 pm
ORH
-
EYW
1 stop20h 23m
American Airlines
Fri 5/297:29 pm
EYW
-
ORH
2 stops21h 24m
American Airlines
Deal found 2/18$292
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:18 pm
ORH
-
EYW
2 stops25h 52m
American Airlines
Wed 6/37:40 pm
EYW
-
ORH
2 stops21h 13m
American Airlines
Deal found 2/16$297
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:44 pm
ORH
-
EYW
2 stops27h 05m
American Airlines
Sun 3/227:42 pm
EYW
-
ORH
2 stops17h 37m
American Airlines
Deal found 2/16$298
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/31:30 pm
ORH
-
EYW
2 stops23h 45m
American Airlines
Sat 3/77:36 pm
EYW
-
ORH
2 stops16h 43m
American Airlines
Deal found 2/15$307
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/122:39 pm
ORH
-
EYW
2 stops8h 19m
American Airlines
Fri 4/175:42 pm
EYW
-
ORH
1 stop20h 32m
American Airlines
Deal found 2/15$317
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:18 pm
ORH
-
EYW
2 stops19h 49m
American Airlines
Thu 5/287:40 pm
EYW
-
ORH
2 stops21h 13m
American Airlines
Deal found 2/16$337
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:30 pm
ORH
-
EYW
2 stops8h 52m
American Airlines
Sun 3/87:42 pm
EYW
-
ORH
2 stops17h 37m
American Airlines
Deal found 2/16$343

Find flight deals from Worcester to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Worcester (ORH) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$212
(American Airlines)

One-way from

$185
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$448
Provider with most accurate pricing for Worcester-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Worcester-Key West flights.
Search Deals
From Worcester to Key West
Search Deals
One-way flight from Worcester to Key West
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($89 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Worcester 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 February 19, 2026.
Use the filters below to find and compare flights from Worcester to Key West that are best for you.

Fly from

Worcester

Fly to

Key West

Route

Depart

Return

Price

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 4/12

2:39 pm-4:30 pm

2 stops25h 51m

Key West

Thu 4/16

5:42 pm-2:14 pm

1 stop20h 32m

$212

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 4/12

2:39 pm-4:30 pm

2 stops25h 51m

Key West

Fri 4/17

3:58 pm-2:14 pm

2 stops22h 16m

$217

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Wed 4/8

2:39 pm-4:30 pm

2 stops25h 51m

Key West

Mon 4/13

3:58 pm-2:14 pm

2 stops22h 16m

$217

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 4/13

2:39 pm-4:35 pm

2 stops25h 56m

Key West

Fri 4/17

2:01 pm-2:14 pm

2 stops24h 13m

$217

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Thu 4/16

2:39 pm-4:30 pm

2 stops25h 51m

Key West

Mon 4/20

3:58 pm-2:14 pm

2 stops22h 16m

$248

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Thu 3/5

1:30 pm-1:15 pm

2 stops23h 45m

Key West

Mon 3/9

7:42 pm-1:19 pm

2 stops17h 37m

$257

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 5/30

5:18 pm-1:41 pm

1 stop20h 23m

Key West

Tue 6/2

7:29 pm-4:53 pm

2 stops21h 24m

$292

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 4/19

2:39 pm-10:54 am

2 stops20h 15m

$185

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 4/20

2:39 pm-4:35 pm

2 stops25h 56m

$185

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 4/20

5:24 pm-12:40 pm

1 stop19h 16m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 11 results
1
2

Compare providers for flights from Worcester to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Worcester to Key West in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Worcester, Massachusetts-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Worcester, Massachusetts-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Worcester, Massachusetts-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Worcester, Massachusetts-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Worcester, Massachusetts-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Worcester to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Worcester 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 Worcester to Key West

What is the cheapest month to book a flight from Worcester, Massachusetts to Key West?

Currently, August is the cheapest month in which you can book a flight from Worcester, Massachusetts to Key West (average of $112). Flying from Worcester, Massachusetts to Key West in April is currently the most expensive (average of $260). 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.

Related info for your journey

Find useful and relevant information for your journey from Worcester to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Worcester, Massachusetts to Key West?

    American Airlines can get you from Worcester, Massachusetts to Key West in just under 25h 51m. Your travel time can differ by up to . Worcester, Massachusetts and Key West are separated by a distance of 1347 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Worcester 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 Worcester, Massachusetts to Key West?

    Currently, August is the cheapest month in which you can book a flight from Worcester, Massachusetts to Key West (average of $112). Flying from Worcester, Massachusetts to Key West in April is currently the most expensive (average of $260). 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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