$113+ Cheap flights from Massachusetts 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Jun 17 — Jun 241
1 adult, Economy
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Find cheap flights from Massachusetts to Key West with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Key West
Keep the following information in mind while searching for Massachusetts to Key West flight deals. Data was last updated June 12, 2025.
Round-trip from | $237 (American Airlines) |
|---|---|
One-way from | $113 (Mytrip) |
Popular in | April |
Cheapest in | September |
Average price | $454 |
Good round-trip deal | $327 or less |
Good one-way deal | $193 or less |
Find flight deals from Massachusetts to Key West
Cheapest flights from Massachusetts to Key WestExplore the most affordable flight options available from Massachusetts to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Massachusetts to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:15 amBOS - EYW
Nonstop3h 38mJetBlue
Sat 11/112:07 pmEYW - BOS
Nonstop3h 31mJetBlue
Deal found 6/10![JetBlue logo]()
$217
This American Airlines deal was found by Cheapflights users on 6/12. 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 7/95:55 amBOS - EYW
1 stop7h 56mAmerican Airlines
Wed 7/164:58 pmEYW - BOS
1 stop6h 03mAmerican Airlines
Deal found 6/12![American Airlines logo]()
$237
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/311:31 amBOS - EYW
2 stops27h 45mAllegiant Air
Sun 8/104:20 pmEYW - BOS
1 stop15h 51mAllegiant Air
Deal found 6/11![Allegiant Air logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/76:00 amBDL - EYW
1 stop27h 22mBreeze Airways
Thu 7/1010:02 amEYW - BDL
2 stops7h 07mBreeze Airways
Deal found 6/10![Breeze Airways logo]()
$257
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 10/2512:25 pmBOS - EYW
1 stop7h 19mDelta
Thu 10/306:00 pmEYW - BOS
1 stop7h 00mDelta
Deal found 6/10![Delta logo]()
$277
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:15 amBOS - EYW
3 stops32h 50mMultiple Airlines
Sun 8/34:20 pmEYW - BOS
1 stop15h 51mMultiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 9/206:00 amALB - EYW
1 stop7h 08mDelta
Tue 9/307:00 amEYW - ALB
1 stop4h 57mDelta
Deal found 6/10![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 7/156:00 amBDL - EYW
1 stop7h 08mDelta
Tue 7/227:00 amEYW - BDL
1 stop6h 21mDelta
Deal found 6/10![Delta logo]()
$283
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/235:44 amBDL - EYW
1 stop5h 09mAmerican Airlines
Sat 9/2711:25 amEYW - BDL
2 stops12h 04mAmerican Airlines
Deal found 6/10![American Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 6/11. 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 11/73:25 pmORH - EYW
1 stop20h 15mAmerican Airlines
Tue 11/112:00 pmEYW - ORH
2 stops24h 53mAmerican Airlines
Deal found 6/11![American Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/2012:00 pmALB - EYW
2 stops6h 59mAmerican Airlines
Tue 9/3011:25 amEYW - ALB
2 stops10h 34mAmerican Airlines
Deal found 6/10![American Airlines logo]()
$293
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/76:05 amBOS - EYW
1 stop7h 07mUnited Airlines
Sat 7/122:08 pmEYW - BOS
1 stop7h 10mUnited Airlines
Deal found 6/10![United Airlines logo]()
$308
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts 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 June 12, 2025.
Use the filters below to find and compare flights from Massachusetts to Key West that are best for you.
Fly from
Massachusetts
Fly to
Key West
Route
Depart
Return
Price
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Wed 7/9
5:55 am-1:51 pm
1 stop7h 56m
Key West
Wed 7/16
4:58 pm-11:01 pm
1 stop6h 03m
$237
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Sun 8/3
11:31 am-3:16 pm
2 stops27h 45m
Key West
Sun 8/10
4:20 pm-8:11 am
1 stop15h 51m
$256
HartfordKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Mon 7/7
6:00 am-9:22 am
1 stop27h 22m
Key West
Thu 7/10
10:02 am-5:09 pm
2 stops7h 07m
$257
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Tue 7/29
6:15 am-3:05 pm
3 stops32h 50m
Key West
Sun 8/3
4:20 pm-8:11 am
1 stop15h 51m
$278
AlbanyKey West
ALB - EYW
ALBEYW
Albany Intl
Sat 9/20
6:00 am-1:08 pm
1 stop7h 08m
Key West
Tue 9/30
7:00 am-11:57 am
1 stop4h 57m
$283
HartfordKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Tue 7/15
6:00 am-1:08 pm
1 stop7h 08m
Key West
Tue 7/22
7:00 am-1:21 pm
1 stop6h 21m
$283
HartfordKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Tue 7/15
5:36 am-10:48 am
1 stop5h 12m
Key West
Tue 7/22
1:25 pm-10:40 pm
2 stops9h 15m
$288
WorcesterKey West
ORH - EYW
ORHEYW
Worcester
Fri 11/7
3:25 pm-11:40 am
1 stop20h 15m
Key West
Tue 11/11
2:00 pm-2:53 pm
2 stops24h 53m
$292
AlbanyKey West
ALB - EYW
ALBEYW
Albany Intl
Sat 9/20
12:00 pm-6:59 pm
2 stops6h 59m
Key West
Tue 9/30
11:25 am-9:59 pm
2 stops10h 34m
$293
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Wed 7/9
5:35 am-10:51 am
1 stop5h 16m
Key West
Sat 7/12
6:27 pm-1:39 am
1 stop7h 12m
$299
Showing 1-10 of 28 results
Best time to book a flight from Massachusetts to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Massachusetts 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 Massachusetts to Key West
What is the cheapest month to book a flight from Massachusetts to Key West?
Currently, August is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $328). Flying from Massachusetts to Key West in March is currently the most expensive (average of $493). 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.
What is the cheapest time of day to fly from MA to EYW?
Find hourly flight availability from Massachusetts to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
When flying from Massachusetts to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Rainfall in Key West by month
Plan your trip to Key West by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.
Temperature in Key West by month
Plan your trip to Key West by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).
Reviews of airlines servicing Key West
Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated June 12, 2025.
See what other customers who have flown with Breeze Airways, Delta and United Airlines from Massachusetts to Key West have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Boarding
8.3
Entertainment
6.6
Overall
8.1
Comfort
8.2
Crew
8.8
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Food
6.7
Boarding
8.3
Entertainment
6.6
Overall
8.1
Comfort
8.2
Crew
8.8
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Food
6.7
Boarding
8.3
Entertainment
6.6
Overall
8.1
Comfort
8.2
Crew
8.8
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Food
6.7
Boarding
8.3
Entertainment
6.6
Overall
8.1
Comfort
8.2
Crew
8.8
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Food
6.7
Boarding
8.3
Entertainment
6.6
Overall
8.1
Comfort
8.2
Crew
8.8
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Food
6.7
Boarding
8.3
Entertainment
6.6
Overall
8.1
Comfort
8.2
Crew
8.8
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Massachusetts to Key West
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Massachusetts to Key West
Discover the top 5 airlines that operate flights from Massachusetts 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$100 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$145 | Average$378 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$213 | Average$532 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$410 | FlexibilityNo cancel fee | On-time71% |