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$97+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/122:25 pm
EYW
-
BOS
1 stop9h 19m
Spirit Airlines
Thu 2/195:27 am
BOS
-
EYW
1 stop8h 03m
Spirit Airlines
Deal found 1/27$189
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 2/129:46 am
EYW
-
BOS
1 stop12h 15m
Multiple Airlines
Thu 2/1911:31 am
BOS
-
EYW
2 stops21h 38m
Multiple Airlines
Deal found 1/27$217
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:06 pm
EYW
-
BOS
1 stop22h 31m
Multiple Airlines
Sun 2/159:57 am
BOS
-
EYW
2 stops27h 33m
Multiple Airlines
Deal found 1/28$278
This JetBlue deal was found by Cheapflights users on 1/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:00 pm
EYW
-
BOS
Nonstop3h 36m
JetBlue
Mon 2/98:09 am
BOS
-
EYW
Nonstop3h 56m
JetBlue
Deal found 1/26$282
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/131:06 pm
EYW
-
BOS
1 stop8h 55m
Multiple Airlines
Mon 2/166:00 am
BOS
-
EYW
2 stops30h 21m
Multiple Airlines
Deal found 1/28$284
This United Airlines deal was found by Cheapflights users on 1/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/122:15 pm
EYW
-
BOS
2 stops9h 42m
United Airlines
Thu 2/1910:30 am
BOS
-
EYW
2 stops11h 39m
United Airlines
Deal found 1/26$290
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/129:46 am
EYW
-
BOS
1 stop12h 15m
Multiple Airlines
Mon 2/166:10 pm
BOS
-
EYW
2 stops18h 11m
Multiple Airlines
Deal found 1/28$292
This United Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 2/136:40 pm
EYW
-
BOS
1 stop5h 17m
United Airlines
Mon 2/1612:05 pm
BOS
-
EYW
1 stop5h 39m
United Airlines
Deal found 1/28$317
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 3/169:49 am
EYW
-
BOS
2 stops25h 52m
Multiple Airlines
Thu 3/199:00 am
BOS
-
EYW
1 stop25h 11m
Multiple Airlines
Deal found 1/27$319

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(Mytrip)

One-way from

$97
(Priceline)

Popular in

September

Cheapest in

November

Average price

$403

Good round-trip deal

$242 or less

Good one-way deal

$213 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. 8% potential increase in price ($36 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 January 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 January 29, 2026.
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 2/12

2:25 pm-11:44 pm

1 stop9h 19m

Boston Logan Intl

Thu 2/19

5:27 am-1:30 pm

1 stop8h 03m

$189

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 2/12

9:46 am-10:01 pm

1 stop12h 15m

Boston Logan Intl

Thu 2/19

11:31 am-9:09 am

2 stops21h 38m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 2/13

1:06 pm-11:37 am

1 stop22h 31m

Boston Logan Intl

Sun 2/15

9:57 am-1:30 pm

2 stops27h 33m

$278

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 2/13

1:06 pm-10:01 pm

1 stop8h 55m

Boston Logan Intl

Mon 2/16

6:00 am-12:21 pm

2 stops30h 21m

$284

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 2/12

2:15 pm-11:57 pm

2 stops9h 42m

Boston Logan Intl

Thu 2/19

10:30 am-10:09 pm

2 stops11h 39m

$290

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 2/13

6:40 pm-11:57 pm

1 stop5h 17m

Boston Logan Intl

Mon 2/16

12:05 pm-5:44 pm

1 stop5h 39m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Mon 3/16

9:49 am-11:41 am

2 stops25h 52m

Boston Logan Intl

Thu 3/19

9:00 am-10:11 am

1 stop25h 11m

$319

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 2/12

2:15 pm-9:51 pm

1 stop7h 36m

Boston Logan Intl

Mon 2/16

12:05 pm-5:44 pm

1 stop5h 39m

$321

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 2/27

6:40 pm-11:57 pm

1 stop5h 17m

Boston Logan Intl

Mon 3/2

6:00 am-1:15 pm

1 stop7h 15m

$327

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 3/11

11:51 am-10:01 pm

1 stop10h 10m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 20 results
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 January.
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 $321). 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 January 29, 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 January 29, 2026.
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
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
JetBlue
7.2
Good
2,892 reviews
American Airlines
7.2
Good
11,205 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 is 1 outbound flight from Key West to Logan Intl offered by 2 different airlines.

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

    Spirit Airlines can get you from Key West to Boston in just under 9h 19m. Your travel time can differ by up to . The distance between Key West and Boston is about 1374 mi.

  • 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 $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 (82%), TAP AIR PORTUGAL (81%) and American Airlines (71%).

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

    On average you can expect to pay $287 for a flight from Key West to Boston. The cheapest flight overall is $109 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $258.

  • 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 $321). 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
Hampton Beach
Watertown
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$347FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$442FlexibilityNo cancel feeOn-time62%

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