What is the cheapest airline that flies from Key West to Massachusetts?

Breeze Airways, Delta, and American Airlines are the most popular carriers operating from Key West to Massachusetts

When did momondo last update prices for flights from Key West Airport to Massachusetts?

Prices for flights from Key West Airport to Massachusetts are refreshed on a daily basis.

How many operators does momondo search for flights from Key West Airport to Massachusetts?

There are 2 operators available for flights from Key West Airport to Massachusetts as of September 2026.

How old do you have to be to fly from Key West Airport to Massachusetts?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Key West Airport to Massachusetts.

What documentation or ID do you need to fly to Massachusetts?

The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$113 Cheap Flights from Key West to Massachusetts in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Key West to Massachusetts

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:59 am - 12:54 pmEYW Key West-BDL Hartford Bradley Intl

25h 55m1 stop Orlando

8:10 am - 9:24 amBDL Hartford Bradley Intl-EYW Key West

25h 14m1 stop Tampa

$244Breeze Airways

Fri, Oct 2 - Tue, Oct 6

10:59 am - 10:26 pmEYW Key West-BDL Hartford Bradley Intl

11h 27m2 stops Orlando New Bern Coastal Carolina Rgnl

8:10 am - 9:24 amBDL Hartford Bradley Intl-EYW Key West

25h 14m1 stop Tampa

$267Breeze Airways

Fri, Oct 2 - Tue, Oct 6

10:45 am - 9:39 amEYW Key West-BOS Boston Logan Intl

22h 54m2 stops Tampa Fort Lauderdale

11:35 am - 1:12 pmBOS Boston Logan Intl-EYW Key West

25h 37m1 stop Knoxville McGhee Tyson

$282Multiple Airlines

Wed, Dec 2 - Sun, Dec 6

11:09 am - 10:42 amEYW Key West-BOS Boston Logan Intl

23h 33m1 stop Knoxville McGhee Tyson

9:09 am - 11:21 amBOS Boston Logan Intl-EYW Key West

26h 12m2 stops Knoxville McGhee Tyson Tampa St. Petersburg

$288Multiple Airlines

Mon, Oct 26 - Sat, Nov 7

1:55 pm - 5:37 pmEYW Key West-BOS Boston Logan Intl

3h 42mnonstop

7:00 am - 12:43 pmBOS Boston Logan Intl-EYW Key West

5h 43m1 stop Charlotte Douglas

$377American Airlines

Tue, Dec 22 - Tue, Dec 29

2:25 pm - 9:46 pmEYW Key West-BOS Boston Logan Intl

7h 21m1 stop New York LaGuardia

10:19 am - 6:25 pmBOS Boston Logan Intl-EYW Key West

8h 06m1 stop Washington, D.C. Reagan-National

$384American Airlines

Mon, Nov 2 - Wed, Nov 11

1:04 pm - 6:19 pmEYW Key West-BOS Boston Logan Intl

5h 15m1 stop Washington, D.C. Reagan-National

7:06 am - 12:37 pmBOS Boston Logan Intl-EYW Key West

5h 31m1 stop Charlotte Douglas

$387American Airlines

Sat, Nov 21 - Mon, Nov 23

12:29 pm - 4:39 pmEYW Key West-BOS Boston Logan Intl

4h 10mnonstop

8:00 am - 11:39 amBOS Boston Logan Intl-EYW Key West

3h 39mnonstop

$407JetBlue

Thu, Oct 15 - Sun, Oct 18

12:45 pm - 4:19 pmEYW Key West-BOS Boston Logan Intl

3h 34mnonstop

8:00 am - 11:55 amBOS Boston Logan Intl-EYW Key West

3h 55mnonstop

$418JetBlue

Sat, Nov 21 - Mon, Nov 23

1:14 pm - 4:47 pmEYW Key West-BOS Boston Logan Intl

3h 33mnonstop

8:25 am - 12:23 pmBOS Boston Logan Intl-EYW Key West

3h 58mnonstop

$418JetBlue

Wed, Dec 2 - Sun, Dec 6

Cheap last minute flights

Enter your travel dates to find the best prices.

6:11 pm - 10:26 pmEYW Key West-BDL Hartford Bradley Intl

28h 15m2 stops Orlando Sanford Intl New Bern Coastal Carolina Rgnl

7:00 am - 12:19 pmBDL Hartford Bradley Intl-EYW Key West

5h 19m1 stop Tampa

$429Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

7:47 pm - 12:59 amEYW Key West-BOS Boston Logan Intl

5h 12m1 stop Miami

8:10 am - 2:04 pmBOS Boston Logan Intl-EYW Key West

5h 54m1 stop Philadelphia

$473American Airlines

Mon, Sep 21 - Mon, Sep 28

7:47 pm - 12:59 amEYW Key West-BOS Boston Logan Intl

5h 12m1 stop Miami

11:15 am - 7:17 pmBOS Boston Logan Intl-EYW Key West

8h 02m2 stops Philadelphia Miami

$498American Airlines

Mon, Sep 21 - Mon, Sep 28

6:19 pm - 11:59 pmEYW Key West-BDL Hartford Bradley Intl

5h 40m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:53 pmBDL Hartford Bradley Intl-EYW Key West

6h 53m1 stop Atlanta Hartsfield-Jackson

$499Delta

Thu, Sep 24 - Mon, Sep 28

10:21 am - 6:46 pmEYW Key West-BOS Boston Logan Intl

8h 25m2 stops Miami Washington, D.C. Reagan-National

6:00 am - 1:17 pmBOS Boston Logan Intl-EYW Key West

7h 17m2 stops Washington, D.C. Reagan-National Miami

$528American Airlines

Mon, Sep 21 - Mon, Sep 28

1:47 pm - 11:33 pmEYW Key West-BDL Hartford Bradley Intl

9h 46m2 stops Miami Charlotte Douglas

5:30 am - 1:17 pmBDL Hartford Bradley Intl-EYW Key West

7h 47m2 stops Washington, D.C. Reagan-National Miami

$683American Airlines

Thu, Sep 24 - Mon, Sep 28

2:15 pm - 11:59 pmEYW Key West-BDL Hartford Bradley Intl

9h 44m2 stops Newark Washington, D.C. Dulles Intl

6:00 am - 1:29 pmBDL Hartford Bradley Intl-EYW Key West

31h 29m2 stops Washington, D.C. Dulles Intl Newark

$795United Airlines

Thu, Sep 24 - Mon, Sep 28

2:15 pm - 11:59 pmEYW Key West-BDL Hartford Bradley Intl

9h 44m2 stops Newark Washington, D.C. Dulles Intl

6:00 am - 1:29 pmBDL Hartford Bradley Intl-EYW Key West

31h 29m2 stops Washington, D.C. Dulles Intl Newark

$814United Airlines

Thu, Sep 24 - Mon, Sep 28

2:15 pm - 11:59 pmEYW Key West-BDL Hartford Bradley Intl

9h 44m2 stops Newark Washington, D.C. Dulles Intl

6:00 am - 1:29 pmBDL Hartford Bradley Intl-EYW Key West

31h 29m2 stops Washington, D.C. Dulles Intl Newark

$844United Airlines

Thu, Sep 24 - Mon, Sep 28

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American Airlines flights from Key West to Massachusetts

Our best American Airlines deals on Key West to Massachusetts flight tickets

American Airlines

Dec 22

EYW1:55 pmKey West

3h 42m

BOS5:37 pmBoston Logan Intl

Dec 29

BOS7:00 amBoston Logan Intl

5h 43m

1 stop

EYW12:43 pmKey West

$377

American Airlines

Nov 2

EYW2:25 pmKey West

7h 21m

1 stop

BOS9:46 pmBoston Logan Intl

Nov 11

BOS10:19 amBoston Logan Intl

8h 06m

1 stop

EYW6:25 pmKey West

$384

American Airlines

Nov 21

EYW7:37 pmKey West

5h 22m

1 stop

BOS12:59 amBoston Logan Intl

Nov 23

BOS6:00 amBoston Logan Intl

6h 26m

1 stop

EYW12:26 pmKey West

$387

JetBlue flights from Key West to Massachusetts

Our best JetBlue deals on Key West to Massachusetts flight tickets

JetBlue

Oct 15

EYW12:29 pmKey West

4h 10m

BOS4:39 pmBoston Logan Intl

Oct 18

BOS8:00 amBoston Logan Intl

3h 39m

EYW11:39 amKey West

$407

JetBlue

Nov 21

EYW12:45 pmKey West

3h 34m

BOS4:19 pmBoston Logan Intl

Nov 23

BOS8:00 amBoston Logan Intl

3h 55m

EYW11:55 amKey West

$418

JetBlue

Oct 31

EYW12:46 pmKey West

3h 59m

BOS4:45 pmBoston Logan Intl

Nov 2

BOS8:00 amBoston Logan Intl

3h 56m

EYW11:56 amKey West

$440

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestHartford

EYW Key West - BDL Hartford Bradley Intl

EYWBDL

Key West

Fri 10/2

10:59 am-12:54 pm

1 stop25h 55m

Hartford Bradley Intl

Tue 10/6

8:10 am-9:24 am

1 stop25h 14m

$244

Key WestHartford

EYW Key West - BDL Hartford Bradley Intl

EYWBDL

Key West

Fri 10/2

10:59 am-10:26 pm

2 stops11h 27m

Hartford Bradley Intl

Tue 10/6

8:10 am-9:24 am

1 stop25h 14m

$267

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Wed 12/2

10:45 am-9:39 am

2 stops22h 54m

Boston Logan Intl

Sun 12/6

11:35 am-1:12 pm

1 stop25h 37m

$282

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Mon 10/26

11:09 am-10:42 am

1 stop23h 33m

Boston Logan Intl

Sat 11/7

9:09 am-11:21 am

2 stops26h 12m

$288

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Tue 12/22

1:55 pm-5:37 pm

Nonstop3h 42m

Boston Logan Intl

Tue 12/29

7:00 am-12:43 pm

1 stop5h 43m

$377

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Mon 11/2

2:25 pm-9:46 pm

1 stop7h 21m

Boston Logan Intl

Wed 11/11

10:19 am-6:25 pm

1 stop8h 06m

$384

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Sat 11/21

1:04 pm-6:19 pm

1 stop5h 15m

Boston Logan Intl

Mon 11/23

7:06 am-12:37 pm

1 stop5h 31m

$387

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Thu 10/15

12:29 pm-4:39 pm

Nonstop4h 10m

Boston Logan Intl

Sun 10/18

8:00 am-11:39 am

Nonstop3h 39m

$407

Quickest round-trip

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Sat 11/21

12:45 pm-4:19 pm

Nonstop3h 34m

Boston Logan Intl

Mon 11/23

8:00 am-11:55 am

Nonstop3h 55m

$418

Key WestBoston

EYW Key West - BOS Boston Logan Intl

EYWBOS

Key West

Wed 12/2

1:14 pm-4:47 pm

Nonstop3h 33m

Boston Logan Intl

Sun 12/6

8:25 am-12:23 pm

Nonstop3h 58m

$418

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Key West to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Massachusetts?

In general, March is the cheapest month to fly from Key West to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $292. If you aren’t able to travel to Massachusetts during the month of March, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $316.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Thursday is the cheapest day to fly to Massachusetts from Key West. The lowest ticket price found for a Thursday departure recently was $388. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Key West because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $843.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Key West to Massachusetts flights are usually those with departure times in the afternoon. Our users have found flights to Massachusetts in the afternoon for as low as $332. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $497 on average. Flights to Massachusetts from Key West in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Key West to Massachusetts flight route?

Fly from Key West to Boston Logan Intl for the best Key West - Massachusetts flight prices

What cabin class options are available on Key West to Massachusetts flights?

There is only 1 cabin class available to choose from on Key West to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Key West to Massachusetts flights?

No. A direct flight is the cheapest option for a flight between Key West to Massachusetts.

Cheap Key West to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Massachusetts

Best Price Found	$113
Fastest flight time	3h 31m
Direct flights	Every day
Airports in Massachusetts	140 airports

The best one-way flight to Massachusetts from Key West in the past 72 hours is $113. The best round-trip flight deal from Key West to Massachusetts found on momondo in the last 72 hours is $244.

The fastest flight from Key West to Massachusetts takes 3h 31m

Direct flights go from Key West to Massachusetts every day.

There are 140 airports in Massachusetts. From Key West there are direct flights to Boston Logan Intl (BOS).

Search flight deals

Frequently asked questions about flying from Key West to Massachusetts

When did momondo last update prices for flights from Key West Airport to Massachusetts?
Prices for flights from Key West Airport to Massachusetts are refreshed on a daily basis.
How many operators does momondo search for flights from Key West Airport to Massachusetts?
There are 2 operators available for flights from Key West Airport to Massachusetts as of September 2026.
How old do you have to be to fly from Key West Airport to Massachusetts?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Key West Airport to Massachusetts.
What documentation or ID do you need to fly to Massachusetts?
The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Key West to Massachusetts?
momondo data reveals that the most frequently booked plane model on the route from Key West to Massachusetts is Airbus A220-300, representing 50.00% of all bookings. The subsequent popular models are Boeing 737-700 at 25.00% and Embraer 175 at 25.00%.

Best airlines flying from Key West to Massachusetts

Compare and see reviews for airlines that fly from Key West to Massachusetts with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $251	Free Cancellation	Rating 7.1 3,035 reviews		Search JetBlue flights
American Airlines	PriceFrom $289	Free Cancellation	Rating 7.1 12,076 reviews		Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Massachusetts?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Key West to Massachusetts. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Key West to Massachusetts with flexible booking policies on momondo?

Flights from Key West to Massachusetts with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Key West to Massachusetts?

Once you have performed a search for Key West to Massachusetts flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Key West to Massachusetts right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Key West to Massachusetts now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Massachusetts and let you know when they change.