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$108+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

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.
Thu 5/287:40 pm
EYW
-
BOS
1 stop5h 19m
American Airlines
Wed 6/38:00 am
BOS
-
EYW
1 stop5h 41m
American Airlines
Deal found 4/28$197
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.
Thu 5/213:55 pm
EYW
-
BOS
1 stop9h 19m
United Airlines
Tue 5/267:19 am
BOS
-
EYW
1 stop7h 48m
United Airlines
Deal found 4/28$265
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 5/225:37 pm
EYW
-
BOS
1 stop6h 12m
American Airlines
Mon 5/257:00 am
BOS
-
EYW
1 stop5h 16m
American Airlines
Deal found 4/28$278
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:14 pm
EYW
-
BOS
2 stops36h 10m
Multiple Airlines
Sat 5/167:00 am
BOS
-
EYW
1 stop28h 25m
Multiple Airlines
Deal found 4/27$286
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2210:31 am
EYW
-
BOS
1 stop22h 24m
Multiple Airlines
Mon 5/2512:01 pm
BOS
-
EYW
2 stops47h 05m
Multiple Airlines
Deal found 4/27$301
This United Airlines deal was found by Cheapflights users on 4/24. 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 5/14:05 pm
EYW
-
BOS
1 stop7h 30m
United Airlines
Fri 5/87:30 am
BOS
-
EYW
1 stop7h 37m
United Airlines
Deal found 4/24$302
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.
Thu 7/305:34 pm
EYW
-
BOS
1 stop6h 15m
American Airlines
Mon 8/38:05 am
BOS
-
EYW
1 stop8h 03m
American Airlines
Deal found 4/28$307
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2210:31 am
EYW
-
BOS
1 stop22h 24m
Multiple Airlines
Fri 5/298:44 am
BOS
-
EYW
2 stops29h 14m
Multiple Airlines
Deal found 4/27$312
This American Airlines deal was found by Cheapflights users on 4/24. 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 9/301:59 pm
EYW
-
BOS
2 stops8h 29m
American Airlines
Wed 10/711:00 am
BOS
-
EYW
2 stops7h 24m
American Airlines
Deal found 4/24$317
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 7/910:55 am
EYW
-
BOS
1 stop22h 19m
Multiple Airlines
Tue 7/146:00 am
BOS
-
EYW
2 stops29h 06m
Multiple Airlines
Deal found 4/26$327

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$265
(United Airlines)

One-way from

$108
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$627

Good round-trip deal

$627 or less

Good one-way deal

$312 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. 13% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 28, 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 5/21

3:55 pm-1:14 am

1 stop9h 19m

Boston Logan Intl

Tue 5/26

7:19 am-3:07 pm

1 stop7h 48m

$265

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 5/29

12:07 pm-9:42 pm

1 stop9h 35m

Boston Logan Intl

Sun 5/31

7:00 am-11:27 am

1 stop28h 27m

$303

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 9/11

6:00 pm-1:06 am

1 stop7h 06m

Boston Logan Intl

Tue 9/15

9:05 am-5:14 pm

1 stop8h 09m

$307

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 5/21

7:40 pm-12:59 am

1 stop5h 19m

Boston Logan Intl

Tue 5/26

6:00 am-1:41 pm

1 stop7h 41m

$307

Key WestBoston

EYW - BOS

EYWBOS

Key West

Mon 8/3

7:29 pm-12:36 am

1 stop5h 07m

Boston Logan Intl

Tue 8/4

8:03 am-1:40 pm

1 stop5h 37m

$347

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 9/10

6:00 pm-1:06 am

1 stop7h 06m

Boston Logan Intl

Tue 9/15

7:30 am-7:45 pm

2 stops12h 15m

$366

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 5/9

4:05 pm-12:59 am

1 stop8h 54m

Boston Logan Intl

Wed 5/13

6:00 am-1:45 pm

1 stop7h 45m

$373

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 9/5

3:10 pm-10:49 pm

1 stop7h 39m

Boston Logan Intl

Mon 9/14

5:45 am-1:09 pm

1 stop7h 24m

$393

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sun 8/16

2:30 pm-11:07 pm

1 stop8h 37m

Boston Logan Intl

Sun 8/23

5:41 am-12:11 pm

1 stop6h 30m

$393

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 9/5

4:05 pm-1:05 am

1 stop9h 00m

Boston Logan Intl

Sat 9/12

9:30 am-10:11 pm

2 stops12h 41m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 April.
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 $627). 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 April 28, 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.

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 April 28, 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
2,968 reviews

Boarding

7.3

Food

6.6

Crew

7.9

Comfort

7.5

Entertainment

7.2

Overall

7.2

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
2,968 reviews
JetBlue
7.2
Good
2,968 reviews

Boarding

7.3

Food

6.6

Crew

7.9

Comfort

7.5

Entertainment

7.2

Overall

7.2

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
11,680 reviews
JetBlue
7.2
Good
2,968 reviews

Boarding

7.3

Food

6.6

Crew

7.9

Comfort

7.5

Entertainment

7.2

Overall

7.2

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.

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

    United Airlines, Delta, and American Airlines can get you from Key West to Boston in just under 5h 19m. Your travel time can differ by up to 4h. 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 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 JetBlue (75%), TAP AIR PORTUGAL (75%) and Qatar Airways (54%).

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

    On average you can expect to pay $603 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 $286.

  • 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 $627). 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
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

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 April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$364FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$251Average$440FlexibilityNo cancel feeOn-time62%

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