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$94+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheap 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 September 19, 2025.

Round-trip from

$222
(United Airlines)

One-way from

$94
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$300

Good round-trip deal

$158 or less

Good one-way deal

$125 or less
From Key West to Boston Logan Intl
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One-way flight from Key West to Boston Logan Intl
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Highest demand for flights based on searches. 17% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Key West to Boston Logan Intl.
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Price to beat on a one-way flight from Key West to Boston Logan Intl.
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Find 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 September 19, 2025.

This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/282:48 pmEYW - BOS
1 stop7h 59mUnited Airlines
Wed 11/56:00 amBOS - EYW
1 stop8h 04mUnited Airlines
Deal found 9/17$222
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/157:52 pmEYW - BOS
1 stop4h 42mAmerican Airlines
Tue 10/287:30 amBOS - EYW
1 stop6h 22mAmerican Airlines
Deal found 9/17$227
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/157:52 pmEYW - BOS
1 stop4h 42mAmerican Airlines
Tue 10/219:20 amBOS - EYW
2 stops7h 56mAmerican Airlines
Deal found 9/17$232
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/211:25 amEYW - BOS
2 stops7h 24mAmerican Airlines
Mon 10/67:30 amBOS - EYW
1 stop6h 22mAmerican Airlines
Deal found 9/17$269
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 10/1811:22 amEYW - BOS
2 stops8h 57mAmerican Airlines
Tue 10/219:20 amBOS - EYW
2 stops7h 56mAmerican Airlines
Deal found 9/17$274
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 9/236:17 pmEYW - BOS
1 stop5h 27mAmerican Airlines
Tue 10/76:00 amBOS - EYW
1 stop7h 52mAmerican Airlines
Deal found 9/17$282
This JetBlue deal was found by Cheapflights users on 9/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:45 pmEYW - BOS
Nonstop3h 30mJetBlue
Sun 11/28:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 9/18$287
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:31 pmEYW - BOS
1 stop5h 28mAmerican Airlines
Wed 10/87:10 amBOS - EYW
1 stop5h 48mAmerican Airlines
Deal found 9/18$297
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:47 pmEYW - BOS
1 stop6h 47mAmerican Airlines
Sat 10/1812:52 pmBOS - EYW
1 stop6h 30mAmerican Airlines
Deal found 9/18$318

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 September 19, 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

Tue 10/28

2:48 pm-10:47 pm

1 stop7h 59m

Boston Logan Intl

Wed 11/5

6:00 am-2:04 pm

1 stop8h 04m

$222

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 10/18

7:52 pm-12:34 am

1 stop4h 42m

Boston Logan Intl

Tue 10/21

6:44 am-1:11 pm

1 stop6h 27m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

7:52 pm-12:34 am

1 stop4h 42m

Boston Logan Intl

Tue 10/28

7:30 am-1:52 pm

1 stop6h 22m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

7:52 pm-12:34 am

1 stop4h 42m

Boston Logan Intl

Tue 10/21

6:44 am-1:11 pm

1 stop6h 27m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 10/21

3:20 pm-10:10 pm

2 stops6h 50m

Boston Logan Intl

Fri 10/24

7:30 am-1:52 pm

1 stop6h 22m

$232

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 10/24

2:14 pm-7:55 pm

1 stop5h 41m

Boston Logan Intl

Tue 10/28

6:00 am-12:55 pm

2 stops6h 55m

$232

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 10/14

6:17 pm-1:13 am

1 stop6h 56m

Boston Logan Intl

Tue 10/21

9:05 am-5:21 pm

1 stop8h 16m

$237

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 11/14

8:55 am-8:28 am

1 stop23h 33m

$94

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 10/18

1:04 pm-4:56 pm

Nonstop3h 52m

$114

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 10/16

6:17 pm-1:13 am

1 stop6h 56m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 17 results
1
2

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, January is the cheapest month in which you can book a flight from Key West to Boston (average of $218). Flying from Key West to Boston in July is currently the most expensive (average of $311). 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 September 19, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 32% on flights from Key West to Boston by exploring options for tickets in the afternoon.

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 September 19, 2025.
Get a feel of what it's like to fly with Delta, 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.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

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
7.2
Good
2,911 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.9

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?

    United Airlines and American Airlines can get you from Key West to Boston in just under 4h 42m. Your travel time can differ by up to 3h 17m. 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 $216. Other airlines that can offer you cheap pricing are JetBlue, from $236, and American Airlines, from $258. Users have found that Delta is 44% cheaper than the other options available to this destination.

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

    On average you can expect to pay $202 for a flight from Key West to Boston. The cheapest flight overall is $125 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $262.

  • 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, January is the cheapest month in which you can book a flight from Key West to Boston (average of $218). Flying from Key West to Boston in July is currently the most expensive (average of $311). 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
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$399FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$502FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$258Average$340FlexibilityNo cancel feeOn-time71%

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