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$247+ Cheap flights from Worcester, MA to Key West (ORH - EYW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — EYW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find 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 November 20, 2025.

This American Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 12/53:30 pmORH - EYW
2 stops24h 16mAmerican Airlines
Tue 12/96:33 pmEYW - ORH
2 stops20h 32mAmerican Airlines
Deal found 11/20$247
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:45 pmORH - EYW
2 stops24h 29mAmerican Airlines
Fri 1/95:24 pmEYW - ORH
1 stop20h 34mAmerican Airlines
Deal found 11/19$249
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:34 pmORH - EYW
2 stops19h 04mAmerican Airlines
Mon 12/88:05 pmEYW - ORH
2 stops19h 04mAmerican Airlines
Deal found 11/19$307
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/63:37 pmORH - EYW
1 stop20h 35mAmerican Airlines
Tue 12/96:33 pmEYW - ORH
2 stops20h 32mAmerican Airlines
Deal found 11/18$354
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/63:37 pmORH - EYW
1 stop20h 35mAmerican Airlines
Mon 12/88:05 pmEYW - ORH
2 stops19h 04mAmerican Airlines
Deal found 11/18$382
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Fri 12/53:30 pmORH - EYW
2 stops22h 11mAmerican Airlines
Mon 12/88:05 pmEYW - ORH
2 stops19h 04mAmerican Airlines
Deal found 11/18$387
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/63:37 pmORH - EYW
2 stops19h 01mAmerican Airlines
Sun 12/78:05 pmEYW - ORH
2 stops18h 57mAmerican Airlines
Deal found 11/18$514
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/281:45 pmORH - EYW
2 stops22h 23mAmerican Airlines
Sat 1/38:09 pmEYW - ORH
2 stops17h 08mAmerican Airlines
Deal found 11/18$577
This Delta deal was found by Cheapflights users on 11/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:05 pmORH - EYW
1 stop20h 55mDelta
Mon 12/87:40 amEYW - ORH
2 stops7h 45mDelta
Deal found 11/18$622

Cheap 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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$394
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
Highest demand for flights based on searches. 18% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 20, 2025.
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

Fri 12/5

3:30 pm-3:46 pm

2 stops24h 16m

Key West

Tue 12/9

6:33 pm-3:05 pm

2 stops20h 32m

$247

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Tue 12/30

1:45 pm-2:14 pm

2 stops24h 29m

Key West

Fri 1/9

5:24 pm-1:58 pm

1 stop20h 34m

$249

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 4/20

4:26 pm-1:37 pm

1 stop21h 11m

Key West

Fri 4/24

5:14 pm-2:53 pm

1 stop21h 39m

$272

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 1/24

2:23 pm-1:16 pm

1 stop22h 53m

Key West

Wed 1/28

4:37 pm-1:53 pm

2 stops21h 16m

$282

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Fri 2/27

1:44 pm-11:23 am

2 stops21h 39m

Key West

Mon 3/2

11:47 am-1:19 pm

2 stops25h 32m

$287

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Thu 12/4

3:34 pm-10:38 am

2 stops19h 04m

Key West

Mon 12/8

8:05 pm-3:09 pm

2 stops19h 04m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Worcester, Massachusetts-Key West flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, June is the cheapest month in which you can book a flight from Worcester, Massachusetts to Key West (average of $137). Flying from Worcester, Massachusetts to Key West in April is currently the most expensive (average of $263). 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 24h 16m. 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, June is the cheapest month in which you can book a flight from Worcester, Massachusetts to Key West (average of $137). Flying from Worcester, Massachusetts to Key West in April is currently the most expensive (average of $263). 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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