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$155+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Apr 18 — Apr 251
Sat 4/18
Sat 4/25
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 March 19, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/212:25 pm
EYW
-
BOS
1 stop11h 34m
Spirit Airlines
Wed 4/85:45 am
BOS
-
EYW
1 stop5h 45m
Spirit Airlines
Deal found 3/16$258
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Thu 5/712:05 pm
EYW
-
BOS
1 stop21h 24m
Multiple Airlines
Sun 5/1010:25 am
BOS
-
EYW
1 stop25h 02m
Multiple Airlines
Deal found 3/18$283
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Thu 4/169:58 am
EYW
-
BOS
1 stop23h 11m
Multiple Airlines
Thu 4/238:16 pm
BOS
-
EYW
1 stop17h 19m
Multiple Airlines
Deal found 3/18$288
This Expedia deal was found by Cheapflights users on 3/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:25 pm
EYW
-
BOS
1 stop11h 34m
Spirit Airlines
Thu 4/235:55 am
BOS
-
EYW
1 stop5h 36m
Spirit Airlines
Deal found 3/15$294
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:25 pm
EYW
-
BOS
2 stops12h 48m
Multiple Airlines
Sat 4/47:14 pm
BOS
-
EYW
1 stop13h 52m
Multiple Airlines
Deal found 3/16$296
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:26 pm
EYW
-
BOS
1 stop11h 31m
Spirit Airlines
Thu 4/235:55 am
BOS
-
EYW
1 stop5h 36m
Spirit Airlines
Deal found 3/17$298
This Expedia deal was found by Cheapflights users on 3/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/212:25 pm
EYW
-
BOS
1 stop11h 34m
Spirit Airlines
Mon 4/65:45 am
BOS
-
EYW
1 stop7h 52m
Spirit Airlines
Deal found 3/18$299
This Delta deal was found by Cheapflights users on 3/18. 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 5/66:23 pm
EYW
-
BOS
1 stop6h 52m
Delta
Tue 5/192:00 pm
BOS
-
EYW
1 stop5h 49m
Delta
Deal found 3/18$307
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Thu 4/24:22 pm
EYW
-
BOS
2 stops31h 37m
Multiple Airlines
Mon 4/65:45 am
BOS
-
EYW
1 stop7h 52m
Multiple Airlines
Deal found 3/18$317
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:01 am
EYW
-
BOS
2 stops12h 58m
Multiple Airlines
Thu 4/238:16 pm
BOS
-
EYW
1 stop17h 19m
Multiple Airlines
Deal found 3/15$334

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 March 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$258
(Cheapflightsfares)

One-way from

$155
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$387

Good round-trip deal

$317 or less

Good one-way deal

$322 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. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Key West to Boston Logan Intl.
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 March 19, 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

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/9

6:22 pm-11:59 pm

1 stop5h 37m

Boston Logan Intl

Mon 4/13

7:00 am-2:51 pm

1 stop7h 51m

$458

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 4/18

3:52 pm-12:59 am

1 stop9h 07m

Boston Logan Intl

Fri 4/24

5:45 am-5:39 pm

2 stops11h 54m

$504
Quickest round-trip

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/9

12:30 pm-4:04 pm

Nonstop3h 34m

Boston Logan Intl

Mon 4/13

8:00 am-11:38 am

Nonstop3h 38m

$512
Cheapest one-way

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sun 5/10

12:05 pm-11:44 pm

2 stops35h 39m

$169

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 6/17

2:26 pm-9:53 pm

1 stop7h 27m

$174

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 9/12

7:00 am-1:54 pm

1 stop6h 54m

$174

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 7/22

6:00 pm-1:03 am

1 stop7h 03m

$174

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 9/10

6:00 pm-1:06 am

1 stop7h 06m

$174

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 6/16

6:00 pm-1:03 am

1 stop7h 03m

$194

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 7/22

1:38 pm-10:29 pm

2 stops8h 51m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 13 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 March.
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 $170). Flying from Key West to Boston in May is currently the most expensive (average of $320). 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 BOS?

Find hourly flight availability from Key West to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 19, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Key West to Boston as you normally would.

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 March 19, 2026.
Get a feel of what it's like to fly with JetBlue and American Airlines 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.
JetBlue
7.2
Good
2,909 reviews

Overall

7.2

Entertainment

7.2

Boarding

7.4

Crew

8.0

Comfort

7.5

Food

6.6

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.
JetBlue
7.2
Good
2,909 reviews
JetBlue
7.2
Good
2,909 reviews

Overall

7.2

Entertainment

7.2

Boarding

7.4

Crew

8.0

Comfort

7.5

Food

6.6

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.
American Airlines
7.1
Good
11,475 reviews
JetBlue
7.2
Good
2,909 reviews

Overall

7.2

Entertainment

7.2

Boarding

7.4

Crew

8.0

Comfort

7.5

Food

6.6

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

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.

  • What airports do I use to fly from Key West to Boston?

    To fly from Key West to Boston, you need to book a flight from Key West (EYW) to Logan Intl (BOS). Nonstop flights to Boston Logan Intl from Key West take 3h 34m on average. When it comes time to book airfare, you have a few options: there are 3 outbound flights from Key West to Logan Intl offered by 2 different airlines.

  • How long is the flight from Key West to Boston?

    United Airlines and JetBlue can get you from Key West to Boston in just under 3h 34m. Your travel time can differ by up to 2h 03m. 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. Another airline that can offer you cheap pricing is JetBlue. Users have found that American Airlines is 52% 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 $133 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 Qatar Airways (69%), JetBlue (67%) and TAP AIR PORTUGAL (65%).

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

    On average you can expect to pay $408 for a flight from Key West to Boston. The cheapest flight overall is $243 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $278.

  • 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 $170). Flying from Key West to Boston in May is currently the most expensive (average of $320). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Chelsea
Smithfield
Lincoln
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Key West to Boston

Discover the top 2 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 March 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$364FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$251Average$442FlexibilityNo cancel feeOn-time62%

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