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$112+ Cheap flights from Key West to Boston (EYW - BOS)

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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Jun 16 — Jun 231
Tue 6/16
Tue 6/23
1 adult, Economy
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Cheap flight deals from Key West to Boston

Cheapest flights from Key West to Boston
Explore the most affordable flight options available from Key West to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:07 am
EYW
-
BOS
1 stop23h 59m
Multiple Airlines
Tue 6/99:10 am
BOS
-
EYW
2 stops25h 56m
Multiple Airlines
Deal found 5/14$270
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:31 am
EYW
-
BOS
1 stop22h 34m
Allegiant Air
Sat 8/1510:59 am
BOS
-
EYW
2 stops24h 28m
Allegiant Air
Deal found 5/14$298
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2911:07 am
EYW
-
BOS
1 stop23h 59m
Multiple Airlines
Thu 6/410:38 am
BOS
-
EYW
1 stop21h 33m
Multiple Airlines
Deal found 5/14$316
This Delta deal was found by Cheapflights users on 5/13. 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 7/216:18 pm
EYW
-
BOS
1 stop7h 02m
Delta
Tue 8/181:56 pm
BOS
-
EYW
1 stop5h 58m
Delta
Deal found 5/13$317
This American Airlines deal was found by Cheapflights users on 5/13. 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 7/2112:18 pm
EYW
-
BOS
1 stop6h 29m
American Airlines
Tue 8/185:27 am
BOS
-
EYW
2 stops7h 38m
American Airlines
Deal found 5/13$322
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Thu 6/257:40 pm
EYW
-
BOS
1 stop5h 19m
American Airlines
Sun 6/285:31 am
BOS
-
EYW
1 stop8h 10m
American Airlines
Deal found 5/17$327
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:19 pm
EYW
-
BOS
1 stop7h 09m
Delta
Tue 6/95:30 am
BOS
-
EYW
1 stop5h 32m
Delta
Deal found 5/14$332
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Wed 6/31:39 pm
EYW
-
BOS
2 stops8h 56m
American Airlines
Tue 6/98:14 am
BOS
-
EYW
1 stop5h 27m
American Airlines
Deal found 5/17$337
This American Airlines deal was found by Cheapflights users on 5/15. 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 9/231:59 pm
EYW
-
BOS
2 stops7h 46m
American Airlines
Sun 9/276:00 am
BOS
-
EYW
2 stops6h 57m
American Airlines
Deal found 5/15$338
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:31 am
EYW
-
BOS
1 stop22h 34m
Multiple Airlines
Fri 8/1412:04 pm
BOS
-
EYW
2 stops46h 20m
Multiple Airlines
Deal found 5/12$341
This Kiwi.com deal was found by Cheapflights users on 5/13. 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.
Fri 5/2911:07 am
EYW
-
BOS
1 stop23h 59m
Multiple Airlines
Sun 5/3110:30 am
BOS
-
EYW
1 stop23h 11m
Multiple Airlines
Deal found 5/13$342
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Mon 6/157:29 pm
EYW
-
BOS
1 stop5h 11m
American Airlines
Sun 6/218:00 am
BOS
-
EYW
1 stop8h 07m
American Airlines
Deal found 5/17$347

Find flight deals from Key West to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Boston (BOS). 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 May 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$270
(Kiwi.com)

One-way from

$112
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$399

Good one-way deal

$373 or less
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
Search Deals
From Key West to Boston Logan Intl
Search Deals
One-way flight from Key West to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a one-way flight from Key West to Boston Logan Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Boston 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 May 17, 2026.
Use the filters below to find and compare flights from Key West to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 7/21

6:18 pm-1:20 am

1 stop7h 02m

Boston Logan Intl

Tue 8/18

1:56 pm-7:54 pm

1 stop5h 58m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 7/30

1:47 pm-9:45 pm

1 stop7h 58m

Boston Logan Intl

Mon 8/3

6:00 am-1:40 pm

1 stop7h 40m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 7/29

4:00 pm-11:21 pm

1 stop7h 21m

Boston Logan Intl

Tue 8/4

7:19 am-3:19 pm

1 stop8h 00m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 7/21

1:47 pm-9:45 pm

1 stop7h 58m

Boston Logan Intl

Fri 7/24

11:19 am-6:48 pm

1 stop7h 29m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 6/2

6:19 pm-1:28 am

1 stop7h 09m

Boston Logan Intl

Tue 6/9

6:50 am-1:28 pm

1 stop6h 38m

$332

Key WestBoston

EYW - BOS

EYWBOS

Key West

Mon 8/3

6:15 pm-1:25 am

1 stop7h 10m

Boston Logan Intl

Tue 8/4

9:55 am-5:20 pm

1 stop7h 25m

$357

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 8/4

2:26 pm-9:55 pm

1 stop7h 29m

Boston Logan Intl

Thu 8/6

7:19 am-3:19 pm

1 stop8h 00m

$377

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 6/17

11:46 am-1:27 am

2 stops13h 41m

Boston Logan Intl

Sat 6/20

12:03 pm-10:06 am

1 stop22h 03m

$411
Cheapest one-way

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 6/10

6:24 pm-1:31 am

1 stop7h 07m

$179

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 8/11

6:15 pm-1:25 am

1 stop7h 10m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/17

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Compare providers for flights from Key West to Boston

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 Key West to Boston in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Key West-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Boston flights, Cheapflights users trust FlightHub the most. FlightHub 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 Key West-Boston 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 Key West to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston 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.

Cheapflights Insights

Everything you need to know about your flight from Key West to Boston

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

Currently, November is the cheapest month in which you can book a flight from Key West to Boston (average of $301). Flying from Key West to Boston in April is currently the most expensive (average of $609). 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.

How much does it cost to fly round-trip from Key West to Boston?

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated May 17, 2026.
Get a feel of what it's like to fly with Delta,American Airlines, andJetBlue from Key West to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,449 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,449 reviews
Delta
7.9
Good
8,449 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.1
Good
11,654 reviews
Delta
7.9
Good
8,449 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.1
Good
2,976 reviews
Delta
7.9
Good
8,449 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.8

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Key West to Boston. 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 Key West to Boston?

    Delta, American Airlines, and United Airlines can get you from Key West to Boston in just under 7h 02m. Your travel time can differ by up to 56m. The distance between Key West and Boston is about 1374 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Key West to Boston round-trip?

    Cheapflights users have booked flights from Key West to Boston round-trip from $182. Other airlines that can offer you cheap pricing are Delta, from $239, and JetBlue, from $251. Users have found that American Airlines is 53% cheaper than the other options available to this destination.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $109. Users have also found prices from $128 and $148 on American Airlines and United Airlines, respectively.

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

    The top 3 most reliable airlines when flying from Key West to Boston are Republic Airways (100%), Qatar Airways (88%) and American Airlines (83%).

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

    On average you can expect to pay $378 for a flight from Key West to Boston. The cheapest flight overall is $283 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $298.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Key West to Boston (average of $301). Flying from Key West to Boston in April is currently the most expensive (average of $609). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Waltham
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
York Beach
Seabrook
Londonderry
Swansea
Old Orchard Beach
Auburn
Quincy
Lowell

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Key West to Boston

Discover the top 3 airlines that operate flights from Key West to Boston. 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 May 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$347FlexibilityNo cancel feeOn-time71%
DeltaCheapest$239Average$316FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$251Average$440FlexibilityNo cancel feeOn-time62%

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