$117+ Cheap flights from Key West to Boston (EYW - BOS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Boston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to Boston
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Cheapest flights from Key West to BostonExplore 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 11, 2026.
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 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2611:09 am -
1 stop23h 33m
Wed 11/412:39 pm -
2 stops21h 40m
Deal found 9/9![Multiple Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/214:58 pm -
1 stop7h 01m
Mon 11/2312:39 pm -
1 stop5h 53m
Deal found 9/10![American Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/7. 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 12/312:41 pm -
1 stop9h 17m
Tue 12/86:00 am -
2 stops9h 26m
Deal found 9/7![United Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/1910:48 am -
1 stop22h 58m
Sat 11/2111:06 am -
1 stop24h 12m
Deal found 9/8![Multiple Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/9. 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 12/222:30 pm -
1 stop6h 24m
Tue 12/297:00 am -
1 stop5h 43m
Deal found 9/9![American Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Sat 9/264:20 pm -
1 stop8h 34m
Mon 9/286:00 am -
1 stop7h 29m
Deal found 9/6![United Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/8. 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 11/192:30 pm -
1 stop7h 13m
Fri 11/207:00 am -
1 stop7h 00m
Deal found 9/8![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/252:15 pm -
1 stop6h 01m
Tue 9/295:40 am -
1 stop7h 37m
Deal found 9/9![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/37:47 pm -
1 stop5h 12m
Sat 10/1011:08 am -
1 stop8h 25m
Deal found 9/10![American Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/151:43 pm -
2 stops8h 50m
Thu 10/227:55 am -
1 stop5h 59m
Deal found 9/10![American Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 9/217:47 pm -
1 stop5h 12m
Fri 9/255:00 am -
1 stop8h 17m
Deal found 9/6![American Airlines logo]()
$417
Best flights from Key West to BostonDiscover carefully curated flight deals from Key West to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
Discover carefully curated flight deals from Key West to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/161:43 pm -
2 stops8h 50m
Sun 10/185:00 am -
1 stop8h 03m
Deal found 9/10![American Airlines logo]()
$407
This Cheapflightsfares deal was found by Cheapflights users on 9/6. 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.
Fri 10/1612:29 pm -
Nonstop4h 10m
Sun 10/188:00 am -
Nonstop3h 39m
Deal found 9/6![JetBlue logo]()
$423
This United Airlines deal was found by Cheapflights users on 9/7. 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 12/312:41 pm -
2 stops11h 08m
Tue 12/85:45 am -
2 stops8h 51m
Deal found 9/7![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 9/9. 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 11/52:50 pm -
1 stop7h 09m
Sun 11/86:00 am -
1 stop7h 52m
Deal found 9/9![United Airlines logo]()
$457
This JetBlue deal was found by Cheapflights users on 9/10. 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 11/512:46 pm -
Nonstop3h 59m
Sun 11/88:00 am -
Nonstop3h 56m
Deal found 9/10![JetBlue logo]()
$472
Last-minute flights from Key West to BostonDiscover last-minute flight deals from Key West to Boston. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Boston. Data last updated September 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 9/217:47 pm -
1 stop5h 12m
Fri 9/255:00 am -
1 stop8h 17m
Deal found 9/6![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/252:15 pm -
1 stop6h 01m
Tue 9/295:40 am -
1 stop7h 37m
Deal found 9/9![American Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Sat 9/264:20 pm -
1 stop8h 34m
Mon 9/286:00 am -
1 stop7h 29m
Deal found 9/6![United Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/37:47 pm -
1 stop5h 12m
Sat 10/1011:08 am -
1 stop8h 25m
Deal found 9/10![American Airlines logo]()
$402
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/141:43 pm -
1 stop8h 14m
Mon 10/1911:08 am -
1 stop8h 25m
Deal found 9/9![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/151:43 pm -
2 stops8h 50m
Thu 10/227:55 am -
1 stop5h 59m
Deal found 9/10![American Airlines logo]()
$407
This Cheapflightsfares deal was found by Cheapflights users on 9/6. 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.
Fri 10/1612:29 pm -
Nonstop4h 10m
Sun 10/188:00 am -
Nonstop3h 39m
Deal found 9/6![JetBlue logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2611:09 am -
1 stop23h 33m
Wed 11/412:39 pm -
2 stops21h 40m
Deal found 9/9![Multiple Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Mon 10/268:03 pm -
1 stop4h 56m
Wed 11/410:19 am -
1 stop8h 06m
Deal found 9/9![American Airlines logo]()
$448
One-way flights from Key West to BostonSearch for one-way flight options from Key West to Boston. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
Search for one-way flight options from Key West to Boston. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/211:09 am -
1 stop23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/610:14 am -
1 stop22h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Allegiant Air logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/612:59 pm -
2 stops20h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/2611:09 am -
1 stop23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 12/1011:01 am -
1 stop23h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Allegiant Air logo]()
$139
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $349 (Kiwi.com) |
One-way from | $117 (Kiwi.com) |
Popular in | April |
Cheapest in | March |
Average price | $356 |
Good one-way deal | $258 or less |
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 7,457,451 searches. Data last updated September 11, 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
Cheapest round-trip
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Sun 2/21
9:18 am-9:07 am
1 stop23h 49m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$191
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Sat 11/7
2:00 pm-9:08 pm
1 stop7h 08m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Sat 10/17
6:11 pm-1:20 am
1 stop7h 09m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Tue 10/27
6:10 pm-1:20 am
1 stop7h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Wed 11/11
6:05 pm-1:13 am
1 stop7h 08m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Wed 11/4
7:40 am-2:54 pm
1 stop7h 14m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Wed 10/7
6:10 pm-1:20 am
1 stop7h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Tue 10/6
6:10 pm-1:20 am
1 stop7h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Wed 3/3
6:00 pm-12:58 am
1 stop6h 58m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Quickest round-trip
Key WestBoston
EYW Key West - BOS Boston Logan Intl
EYWBOS
Key West
Wed 3/10
7:00 am-12:39 pm
1 stop5h 39m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
Showing 1-10 of 15 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
EYW-BOS
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, March is the cheapest month in which you can book a flight from Key West to Boston (average of $292). 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.
How much does it cost to fly round-trip from Key West to Boston?
Airfare is typical for this route at the moment.
Key West to Boston flights typically cost between $336 and $571 in October.The cheapest round-trip price found within the last 5 days was $349 on Multiple Airlines (Oct 26-Nov 4).
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 11, 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.
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.8
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.8
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Boarding
7.5
Comfort
7.2
Crew
7.9
Food
6.4
Entertainment
6.8
Overall
7.1
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
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.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Seekonk
Dedham
Cranston
Warwick
Pawtucket
Peabody
Auburn
Revere
York Beach
Londonderry
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 11, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
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Key West and Boston flights
Browse other Key West and Boston flight options. Last updated on September 11, 2026.
Other flights from Key West
Browse through other flights departing from Key West. Flights are based on user searches made on Cheapflights and were last updated on September 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$251 | Average$440 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$289 | Average$383 | FlexibilityNo cancel fee | On-time71% |