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$175+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — EYW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$237
(American Airlines)

One-way from

$175
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$316
From Worcester to Key West
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One-way flight from Worcester to Key West
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Highest demand for flights based on searches. 18% potential increase in price ($92 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/44:24 pmORH - EYW
2 stops21h 05mAmerican Airlines
Sat 10/255:10 pmEYW - ORH
2 stops22h 40mAmerican Airlines
Deal found 9/15$237
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/154:17 pmORH - EYW
2 stops27h 05mAmerican Airlines
Wed 10/227:52 pmEYW - ORH
2 stops19h 58mAmerican Airlines
Deal found 9/15$281
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 11/213:17 pmORH - EYW
2 stops21h 46mAmerican Airlines
Sun 11/231:33 pmEYW - ORH
2 stops25h 18mAmerican Airlines
Deal found 9/17$312
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 12/221:45 pmORH - EYW
1 stop21h 49mAmerican Airlines
Mon 12/298:09 pmEYW - ORH
2 stops17h 08mAmerican Airlines
Deal found 9/16$342
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 9/194:23 pmORH - EYW
2 stops26h 36mAmerican Airlines
Sun 9/217:31 pmEYW - ORH
2 stops20h 25mAmerican Airlines
Deal found 9/15$347
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/14:24 pmORH - EYW
2 stops19h 25mAmerican Airlines
Sun 10/511:25 amEYW - ORH
2 stops28h 25mAmerican Airlines
Deal found 9/16$351
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/104:17 pmORH - EYW
2 stops22h 09mAmerican Airlines
Fri 10/174:57 pmEYW - ORH
2 stops22h 42mAmerican Airlines
Deal found 9/15$383
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/204:24 pmORH - EYW
1 stop21h 36mAmerican Airlines
Wed 9/243:45 pmEYW - ORH
2 stops24h 13mAmerican Airlines
Deal found 9/14$387

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 September 17, 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

Tue 10/7

4:17 pm-12:58 pm

2 stops20h 41m

Key West

Tue 10/28

5:47 pm-3:50 pm

2 stops22h 03m

$237

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 10/4

4:24 pm-1:29 pm

2 stops21h 05m

Key West

Sat 10/25

5:10 pm-3:50 pm

2 stops22h 40m

$237

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Wed 10/15

4:17 pm-7:22 pm

2 stops27h 05m

Key West

Wed 10/22

7:52 pm-3:50 pm

2 stops19h 58m

$281

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Fri 11/21

3:17 pm-1:03 pm

2 stops21h 46m

Key West

Sun 11/23

1:33 pm-2:51 pm

2 stops25h 18m

$312

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 12/22

1:45 pm-11:34 am

1 stop21h 49m

Key West

Mon 12/29

8:09 pm-1:17 pm

2 stops17h 08m

$342

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Wed 10/1

4:24 pm-11:49 am

2 stops19h 25m

Key West

Sun 10/5

11:25 am-3:50 pm

2 stops28h 25m

$351

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 2/15

3:25 pm-1:50 pm

1 stop22h 25m

Key West

Fri 2/20

5:20 pm-2:53 pm

2 stops21h 33m

$352

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 2/15

3:25 pm-1:50 pm

1 stop22h 25m

Key West

Sat 2/21

5:20 pm-2:53 pm

2 stops21h 33m

$352

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 2/15

3:25 pm-11:44 am

1 stop20h 19m

$175

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 2/14

3:25 pm-11:06 am

2 stops19h 41m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 11 results
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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 $328). Flying from Worcester, Massachusetts to Key West in March is currently the most expensive (average of $491). 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 20h 41m. 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 $328). Flying from Worcester, Massachusetts to Key West in March is currently the most expensive (average of $491). 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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