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$73+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:10 pmEYW - BOS
1 stop6h 44mUnited Airlines
Sun 1/410:25 amBOS - EYW
1 stop6h 48mUnited Airlines
Deal found 12/15$217
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:25 pmEYW - BOS
Nonstop3h 34mAmerican Airlines
Wed 12/3110:44 amBOS - EYW
Nonstop4h 11mAmerican Airlines
Deal found 12/16$247
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/314:03 pmEYW - BOS
1 stop7h 30mAmerican Airlines
Sun 1/410:44 amBOS - EYW
Nonstop4h 11mAmerican Airlines
Deal found 12/15$248
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:22 pmEYW - BOS
1 stop9h 22mUnited Airlines
Wed 12/315:20 amBOS - EYW
1 stop6h 21mUnited Airlines
Deal found 12/16$259
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/288:09 pmEYW - BOS
1 stop4h 50mAmerican Airlines
Mon 12/2910:44 amBOS - EYW
Nonstop4h 11mAmerican Airlines
Deal found 12/16$309
This JetBlue deal was found by Cheapflights users on 12/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/191:12 pmEYW - BOS
Nonstop3h 36mJetBlue
Sun 12/288:24 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 12/17$320
This JetBlue deal was found by Cheapflights users on 12/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:12 pmEYW - BOS
Nonstop3h 36mJetBlue
Mon 12/298:24 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 12/16$442
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:10 pmEYW - BOS
1 stop6h 44mUnited Airlines
Mon 12/295:20 amBOS - EYW
1 stop6h 21mUnited Airlines
Deal found 12/16$468

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$175
(Kiwi.com)

One-way from

$73
(Super.com)

Popular in

September

Cheapest in

November

Average price

$410

Good one-way deal

$201 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. 6% potential increase in price ($27 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 December 2025
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 December 18, 2025.
Use the filters below to find and compare flights from Key West to Boston that are best for you.

Fly from

Key West

Fly to

Boston

Route

Depart

Return

Price

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/15

10:06 am-11:19 pm

1 stop13h 13m

Boston Logan Intl

Sat 1/17

5:27 pm-9:26 am

2 stops15h 59m

$197

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 3/4

6:07 pm-1:09 am

1 stop7h 02m

Boston Logan Intl

Tue 3/10

2:00 pm-7:41 pm

1 stop5h 41m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 12/31

5:10 pm-11:54 pm

1 stop6h 44m

Boston Logan Intl

Sun 1/4

10:25 am-5:13 pm

1 stop6h 48m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/8

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

Sun 1/11

6:00 am-3:17 pm

1 stop9h 17m

$277

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 4/15

12:15 pm-11:59 pm

1 stop11h 44m

Boston Logan Intl

Sat 4/25

7:55 pm-11:17 am

1 stop15h 22m

$294

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 4/15

12:15 pm-11:59 pm

1 stop11h 44m

Boston Logan Intl

Sat 4/25

6:29 pm-8:29 pm

2 stops26h 00m

$308

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sun 12/28

8:09 pm-12:59 am

1 stop4h 50m

Boston Logan Intl

Mon 12/29

10:44 am-2:55 pm

Nonstop4h 11m

$309

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 1/3

10:35 pm-8:46 am

2 stops34h 11m

Boston Logan Intl

Wed 1/7

12:29 pm-9:26 am

1 stop20h 57m

$310

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/8

1:00 pm-4:36 pm

Nonstop3h 36m

Boston Logan Intl

Sun 1/11

8:09 am-12:05 pm

Nonstop3h 56m

$326

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/15

5:21 pm-11:43 pm

1 stop6h 22m

Boston Logan Intl

Sat 1/17

8:15 am-12:32 pm

Nonstop4h 17m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 22 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Key West-Boston flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 July is currently the most expensive (average of $316). 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 December 18, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 30% on flights from Key West to Boston by exploring options for tickets in the afternoon.

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 December 18, 2025.
Get a feel of what it's like to fly with American Airlines and JetBlue 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.
American Airlines
7.2
Good
11,054 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
JetBlue
7.2
Good
2,896 reviews
American Airlines
7.2
Good
11,054 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 and United Airlines can get you from Key West to Boston in just under 6h 44m. Your travel time can differ by up to 18m. 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 United Airlines. According to our data, you can fly for as low as $118. Users have also found prices from $128 and $134 on American Airlines and Delta, 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 (76%), TAP AIR PORTUGAL (74%) and Qatar Airways (63%).

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

    On average you can expect to pay $282 for a flight from Key West to Boston. The cheapest flight overall is $177 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $175.

  • 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 July is currently the most expensive (average of $316). 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
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Brockton
Cranston
Lincoln
Lowell
Smithfield
Peabody
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
Waltham
Chelsea

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$347FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$474FlexibilityNo cancel feeOn-time62%

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