$135+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
May 5 — May 121
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 April 30, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $239 (American Airlines) |
One-way from | $135 (Mytrip) |
Popular in | April |
Cheapest in | September |
Average price | $591 |
Good round-trip deal | $426 or less |
Good one-way deal | $173 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 April 30, 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 April 30, 2025.
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/3010:05 amBDL - EYW
1 stop6h 35mAmerican Airlines
Tue 6/35:24 pmEYW - BDL
1 stop5h 19mAmerican Airlines
Deal found 4/28![American Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 10/18:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Mon 10/68:47 amEYW - BDL
2 stops9h 09mBreeze Airways
Deal found 4/29![Breeze Airways logo]()
$253
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/76:08 amALB - EYW
1 stop7h 41mAmerican Airlines
Wed 6/114:54 pmEYW - ALB
1 stop5h 29mAmerican Airlines
Deal found 4/29![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/28. 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 9/610:00 amBDL - EYW
1 stop7h 15mDelta
Fri 9/126:00 pmEYW - BDL
1 stop5h 46mDelta
Deal found 4/28![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 4/27. 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 9/223:25 pmORH - EYW
1 stop22h 15mAmerican Airlines
Mon 10/65:18 pmEYW - ORH
1 stop21h 35mAmerican Airlines
Deal found 4/27![American Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/105:15 amBOS - EYW
1 stop5h 35mAmerican Airlines
Fri 6/131:00 pmEYW - BOS
1 stop6h 18mAmerican Airlines
Deal found 4/29![American Airlines logo]()
$317
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Wed 5/215:45 amBOS - EYW
3 stops35h 00mMultiple Airlines
Tue 5/274:16 pmEYW - BOS
1 stop17h 54mMultiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$323
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Sat 5/1711:00 amBOS - EYW
2 stops21h 03mAllegiant Air
Wed 5/214:46 pmEYW - BOS
2 stops15h 26mAllegiant Air
Deal found 4/29![Allegiant Air logo]()
$332
This United Airlines deal was found by Cheapflights users on 4/28. 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 11/106:00 amBOS - EYW
1 stop9h 06mUnited Airlines
Fri 11/146:45 pmEYW - BOS
2 stops19h 21mUnited Airlines
Deal found 4/28![United Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Sat 9/62:57 pmBDL - EYW
2 stops23h 03mUnited Airlines
Fri 9/122:45 pmEYW - BDL
3 stops30h 55mUnited Airlines
Deal found 4/28![United Airlines logo]()
$369
This JetBlue deal was found by Cheapflights users on 4/29. 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.
Wed 10/158:15 amBOS - EYW
Nonstop3h 35mJetBlue
Wed 10/228:45 amEYW - BOS
1 stop7h 21mJetBlue
Deal found 4/29![JetBlue logo]()
$373
This Delta deal was found by Cheapflights users on 4/29. 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.
Mon 5/125:44 amALB - EYW
2 stops11h 46mDelta
Sat 5/176:25 pmEYW - ALB
1 stop5h 36mDelta
Deal found 4/29![Delta logo]()
$384
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 April 30, 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
HartfordKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Fri 5/30
10:05 am-4:40 pm
1 stop6h 35m
Key West
Tue 6/3
5:24 pm-10:43 pm
1 stop5h 19m
$239
HartfordKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Sun 5/25
2:59 pm-8:07 pm
1 stop5h 08m
Key West
Tue 6/3
6:25 pm-11:59 pm
1 stop5h 34m
$269
AlbanyKey West
ALB - EYW
ALBEYW
Albany Intl
Sat 6/7
6:08 am-1:49 pm
1 stop7h 41m
Key West
Wed 6/11
4:54 pm-10:23 pm
1 stop5h 29m
$269
WorcesterKey West
ORH - EYW
ORHEYW
Worcester
Mon 9/22
3:25 pm-1:40 pm
1 stop22h 15m
Key West
Mon 10/6
5:18 pm-2:53 pm
1 stop21h 35m
$292
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Mon 6/2
7:00 am-12:53 pm
1 stop5h 53m
Key West
Fri 6/6
2:12 pm-8:01 pm
1 stop5h 49m
$317
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Tue 6/10
5:49 am-2:08 pm
2 stops8h 19m
Key West
Tue 6/17
4:54 pm-10:43 pm
1 stop5h 49m
$322
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Wed 5/21
5:45 am-4:45 pm
3 stops35h 00m
Key West
Tue 5/27
4:16 pm-10:10 am
1 stop17h 54m
$323
BostonKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Sat 5/17
11:00 am-8:03 am
2 stops21h 03m
Key West
Wed 5/21
4:46 pm-8:12 am
2 stops15h 26m
$332
AlbanyKey West
ALB - EYW
ALBEYW
Albany Intl
Mon 5/12
5:44 am-5:30 pm
2 stops11h 46m
Key West
Sat 5/17
6:25 pm-12:01 am
1 stop5h 36m
$384
HartfordKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Wed 6/11
6:00 am-6:05 pm
2 stops12h 05m
Key West
Thu 6/12
6:45 pm-11:36 pm
2 stops28h 51m
$388
Showing 1-10 of 22 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 April 30, 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 April 30, 2025.
See what other customers who have flown with Breeze Airways, Alaska Airlines and Delta 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.
Comfort
8.2
Crew
8.8
Entertainment
6.6
Overall
8.1
Boarding
8.3
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Comfort
8.2
Crew
8.8
Entertainment
6.6
Overall
8.1
Boarding
8.3
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Comfort
8.2
Crew
8.8
Entertainment
6.6
Overall
8.1
Boarding
8.3
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Comfort
8.2
Crew
8.8
Entertainment
6.6
Overall
8.1
Boarding
8.3
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Comfort
8.2
Crew
8.8
Entertainment
6.6
Overall
8.1
Boarding
8.3
Food
6.7
Reviews
1 / 11
10.0
ExcellentDena,Dec 2024
LAS - BDL
Comfort
8.2
Crew
8.8
Entertainment
6.6
Overall
8.1
Boarding
8.3
Food
6.7
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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 April 30, 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$211 | Average$536 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$362 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$404 | FlexibilityNo cancel fee | On-time71% |