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$111+ Cheap flights from Key West (EYW) to Massachusetts

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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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Cheap flight deals from Key West to Massachusetts

Keep the following information in mind while searching for Key West to Massachusetts flight deals. Data was last updated February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Mytrip)

One-way from

$111
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$421

Good round-trip deal

$312 or less

Good one-way deal

$219 or less
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
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From Key West to Massachusetts
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One-way flight from Key West to Massachusetts
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Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Key West to Massachusetts.
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Price to beat on a one-way flight from Key West to Massachusetts.
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Find flight deals from Key West to Massachusetts

Cheapest flights from Key West to Massachusetts
Explore the most affordable flight options available from Key West to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2025.

This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:00 pmEYW - BDL
1 stop5h 51mDelta
Wed 6/46:00 amBDL - EYW
1 stop5h 49mDelta
Deal found 2/19$269
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Fri 5/305:30 pmEYW - BDL
2 stops6h 44mAmerican Airlines
Wed 6/46:05 amBDL - EYW
1 stop7h 34mAmerican Airlines
Deal found 2/19$299
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/77:00 amEYW - BOS
1 stop6h 44mDelta
Tue 3/117:00 amBOS - EYW
1 stop5h 50mDelta
Deal found 2/20$327
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/71:54 pmEYW - BOS
2 stops9h 56mUnited Airlines
Tue 3/1111:01 amBOS - EYW
1 stop10h 02mUnited Airlines
Deal found 2/20$333
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/275:27 pmEYW - BDL
2 stops29h 13mMultiple Airlines
Sat 3/12:52 pmBDL - EYW
2 stops25h 45mMultiple Airlines
Deal found 2/20$358
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/142:15 pmEYW - BOS
1 stop6h 51mAmerican Airlines
Fri 3/218:39 amBOS - EYW
1 stop8h 46mAmerican Airlines
Deal found 2/20$423
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/72:00 pmEYW - BOS
1 stop8h 52mJetBlue
Tue 3/118:00 amBOS - EYW
Nonstop3h 56mJetBlue
Deal found 2/20$431
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2710:55 amEYW - BDL
2 stops13h 04mUnited Airlines
Fri 2/287:55 pmBDL - EYW
2 stops14h 15mUnited Airlines
Deal found 2/20$476
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/276:00 pmEYW - BDL
1 stop5h 47mJetBlue
Fri 2/286:00 amBDL - EYW
1 stop8h 20mJetBlue
Deal found 2/20$523

Find flights from Key West to Massachusetts within your budget

Customize your flight search to find flights from Key West to Massachusetts 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 21, 2025.

Fly from

Key West

Fly to

Massachusetts

Route

Depart

Return

Price

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 3/6

4:23 pm-8:37 am

1 stop16h 14m

Boston Logan Intl

Mon 3/10

9:27 am-1:44 pm

1 stop28h 17m

$239

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 5/30

6:00 pm-11:51 pm

1 stop5h 51m

Hartford Bradley Intl

Wed 6/4

6:00 am-11:49 am

1 stop5h 49m

$269

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 3/6

4:23 pm-8:37 am

1 stop16h 14m

Boston Logan Intl

Mon 3/10

1:56 pm-1:44 pm

2 stops23h 48m

$278

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 6/4

2:12 pm-10:24 pm

1 stop8h 12m

Boston Logan Intl

Wed 6/11

6:00 am-12:53 pm

1 stop6h 53m

$297

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 5/30

5:30 pm-12:14 am

2 stops6h 44m

Hartford Bradley Intl

Wed 6/4

6:05 am-1:39 pm

1 stop7h 34m

$299

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 3/7

7:00 am-1:44 pm

1 stop6h 44m

Boston Logan Intl

Tue 3/11

7:00 am-12:50 pm

1 stop5h 50m

$327

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 6/4

5:30 pm-12:16 am

1 stop6h 46m

Boston Logan Intl

Wed 6/11

6:00 am-12:58 pm

2 stops6h 58m

$332

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 5/30

10:55 am-2:17 pm

2 stops27h 22m

Hartford Bradley Intl

Wed 6/4

2:57 pm-6:55 pm

2 stops27h 58m

$394

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 3/6

2:00 pm-10:52 pm

1 stop8h 52m

Boston Logan Intl

Mon 3/10

8:00 am-11:56 am

Nonstop3h 56m

$421

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 3/25

10:07 am-9:59 am

3 stops23h 52m

$111

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 19 results
1
2

Best time to book a flight from Key West to Massachusetts

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

Travel insights for flights from Key West to Massachusetts

Get recent, data-driven insights about flights from Key West to Massachusetts including ideal travel times, pricing trends, and more.

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

Currently, January is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $218). Flying from Key West to Massachusetts in July is currently the most expensive (average of $311). 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 EYW to MA?

Find hourly flight availability from Key West to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 21, 2025.

When flying from Key West to Massachusetts, 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 Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated February 21, 2025.
See what other customers who have flown with Alaska Airlines, Delta and JetBlue from Key West to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,692 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,692 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,220 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

JetBlue
7.4
Good
3,070 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,766 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Allegiant Air
7.3
Good
765 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Food

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

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

  • What airport do you fly from for flights from Key West to Massachusetts?

    If you book a flight to Massachusetts from Key West, you will be flying from Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West.

  • What are the cheapest airlines to fly from Key West to Massachusetts one-way?

    One-way options have recently been found by users for as low as $120 on Allegiant Air. Other airlines that offer cheap prices include JetBlue from $139 and American Airlines from $148 one-way.

  • What are the most popular routes from Key West to Massachusetts?

    The most popular flight routes from Key West to Massachusetts are Key West - Boston Logan Intl, Key West - Hartford Bradley Intl and Key West - Worcester.

  • What are the most reliable airlines from Key West to Massachusetts?

    Consider American Airlines (67%), Republic Airways (67%) or Qatar Airways (66%) when booking your flight. These represent the most reliable airlines when flying from Key West to Massachusetts.

  • What are the cheapest flights from Key West to Massachusetts?

    On average you can expect to pay $507 for a flight from Key West to Massachusetts. The cheapest flight overall is $165 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $239.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $218). Flying from Key West to Massachusetts in July is currently the most expensive (average of $311). 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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Alternative routes for Key West to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Key West to Massachusetts

Discover the top 3 airlines that operate flights from Key West to Massachusetts. 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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$209Average$577FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$371FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$246Average$328FlexibilityNo cancel feeOn-time71%
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