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

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

How many flights depart from Key West to Massachusetts on average per week?

As of March 2026, there are 23 flights per week flying from Key West to Massachusetts. The most common day of the week flights depart is Sat, with 22% of flights taking off on this day.

How many flights depart from Key West to Massachusetts on average per day?

The number of flights available between Key West and Massachusetts is 3 per day as of March 2026. The most frequent departure time is 12:00PM, with 100% of daily flights leaving in the afternoon.

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 March 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.

$135 Cheap Flights from Key West to Massachusetts in 2026

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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.

12:05 pm - 11:11 pm

EYW

BDL

11h 06m

2 stops

6:20 am - 10:27 am

BDL

EYW

28h 07m

1 stop

$255Breeze Airways

Thu, May 28 - Sun, May 31

12:05 pm - 11:11 pm

EYW

BDL

11h 06m

2 stops

6:20 am - 10:27 am

BDL

EYW

28h 07m

1 stop

$261Breeze Airways

Thu, May 28 - Sun, May 31

12:25 pm - 11:59 pm

EYW

BOS

11h 34m

1 stop

5:55 am - 11:31 am

BOS

EYW

5h 36m

1 stop

$269Spirit Airlines

Thu, Apr 9 - Thu, Apr 23

4:22 pm - 10:04 pm

EYW

BDL

5h 42m

1 stop

9:10 am - 11:11 am

BDL

EYW

26h 01m

1 stop

$276Breeze Airways

Thu, Apr 9 - Tue, Apr 14

12:25 pm - 11:59 pm

EYW

BOS

11h 34m

1 stop

5:45 am - 11:30 am

BOS

EYW

5h 45m

1 stop

$278Spirit Airlines

Thu, Apr 2 - Wed, Apr 8

12:05 pm - 9:29 am

EYW

BOS

21h 24m

1 stop

10:25 am - 11:27 am

BOS

EYW

25h 02m

1 stop

$283Multiple Airlines

Thu, May 7 - Sun, May 10

9:58 am - 9:09 am

EYW

BOS

23h 11m

1 stop

8:16 pm - 1:35 pm

BOS

EYW

17h 19m

1 stop

$288Multiple Airlines

Thu, Apr 16 - Thu, Apr 23

6:23 pm - 1:15 am

EYW

BOS

6h 52m

1 stop

2:00 pm - 7:49 pm

BOS

EYW

5h 49m

1 stop

$307Delta

Wed, May 6 - Tue, May 19

7:29 pm - 12:55 am

EYW

BDL

5h 26m

1 stop

5:00 am - 11:01 am

BDL

EYW

6h 01m

1 stop

$323American Airlines

Sat, May 23 - Sat, May 30

7:29 pm - 12:55 am

EYW

BDL

5h 26m

1 stop

9:26 am - 6:49 pm

BDL

EYW

9h 23m

2 stops

$328American Airlines

Sat, May 23 - Sat, May 30

Spirit Airlines flights from Key West to Massachusetts

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

Spirit Airlines

Apr 9

EYW12:25 pmKey West

11h 34m

1 stop

BOS11:59 pmBoston Logan Intl

Apr 23

BOS5:55 amBoston Logan Intl

5h 36m

1 stop

EYW11:31 amKey West

$269

Spirit Airlines

Apr 2

EYW12:25 pmKey West

11h 34m

1 stop

BOS11:59 pmBoston Logan Intl

Apr 8

BOS5:45 amBoston Logan Intl

5h 45m

1 stop

EYW11:30 amKey West

$278

Spirit Airlines

Apr 2

EYW12:25 pmKey West

11h 34m

1 stop

BOS11:59 pmBoston Logan Intl

Apr 8

BOS5:45 amBoston Logan Intl

5h 45m

1 stop

EYW11:30 amKey West

$298

United Airlines flights from Key West to Massachusetts

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

United Airlines

Apr 9

EYW6:22 pmKey West

5h 37m

1 stop

BOS11:59 pmBoston Logan Intl

Apr 23

BOS5:45 amBoston Logan Intl

11h 54m

2 stops

EYW5:39 pmKey West

$312

United Airlines

Jul 10

EYW4:00 pmKey West

9h 08m

1 stop

BOS1:08 amBoston Logan Intl

Jul 13

BOS6:00 amBoston Logan Intl

7h 30m

1 stop

EYW1:30 pmKey West

$381

United Airlines

Jul 30

EYW4:00 pmKey West

9h 08m

1 stop

BOS1:08 amBoston Logan Intl

Aug 3

BOS6:00 amBoston Logan Intl

7h 30m

1 stop

EYW1:30 pmKey West

$387

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 5/28

12:05 pm-11:11 pm

2 stops11h 06m

Hartford Bradley Intl

Sun 5/31

6:20 am-10:27 am

1 stop28h 07m

$255

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 5/28

12:05 pm-11:11 pm

2 stops11h 06m

Hartford Bradley Intl

Sun 5/31

6:20 am-10:27 am

1 stop28h 07m

$261

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/9

12:25 pm-11:59 pm

1 stop11h 34m

Boston Logan Intl

Thu 4/23

5:55 am-11:31 am

1 stop5h 36m

$269

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 4/9

4:22 pm-10:04 pm

1 stop5h 42m

Hartford Bradley Intl

Tue 4/14

9:10 am-11:11 am

1 stop26h 01m

$276

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/2

12:25 pm-11:59 pm

1 stop11h 34m

Boston Logan Intl

Wed 4/8

5:45 am-11:30 am

1 stop5h 45m

$278

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 5/7

12:05 pm-9:29 am

1 stop21h 24m

Boston Logan Intl

Sun 5/10

10:25 am-11:27 am

1 stop25h 02m

$283

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/16

9:58 am-9:09 am

1 stop23h 11m

Boston Logan Intl

Thu 4/23

8:16 pm-1:35 pm

1 stop17h 19m

$288

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 5/6

6:23 pm-1:15 am

1 stop6h 52m

Boston Logan Intl

Tue 5/19

2:00 pm-7:49 pm

1 stop5h 49m

$307

Quickest round-trip

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 5/23

7:29 pm-12:55 am

1 stop5h 26m

Hartford Bradley Intl

Sat 5/30

5:00 am-11:01 am

1 stop6h 01m

$323

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 5/23

7:29 pm-12:55 am

1 stop5h 26m

Hartford Bradley Intl

Sat 5/30

9:26 am-6:49 pm

2 stops9h 23m

$328

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

Other information

What is the cheapest month to fly to Massachusetts?

In general, November 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 $301. If you aren’t able to travel to Massachusetts during the month of November, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $314.

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

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Key West. The lowest ticket price found for a Wednesday departure recently was $292. 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 $583.

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 $408 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 are 2 cabin classes 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?

You could potentially save up to 2% on your flight if you consider stops on a Key West to Massachusetts flight.

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	$293
Fastest flight time	3h 34m
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 $293. The best round-trip flight deal from Key West to Massachusetts found on momondo in the last 72 hours is $317.

The fastest flight from Key West to Massachusetts takes 3h 34m

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

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 March 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 66.67% of all bookings. The subsequent popular models are Embraer 175 at 20.00%, Boeing 737-700 at 6.67%, and Airbus A320-100/200 at 6.67%.

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
American Airlines	PriceFrom $182	Free Cancellation	Rating 7.1 11,486 reviews		Search American Airlines flights
JetBlue	PriceFrom $251	Free Cancellation	Rating 7.2 2,908 reviews		Search JetBlue 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.