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

What airlines fly to Massachusetts?

American Airlines, JetBlue and Delta are the top three most popular airlines that fly to Massachusetts from Key West according to our data. American Airlines is the first choice among our users, with 65% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 3 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

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

As of August 2026, there are 2 flights per week flying from Key West to Massachusetts. The most common day of the week flights depart is Mon, with 50% of flights taking off on this day.

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 3 operators available for flights from Key West Airport to Massachusetts as of August 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.

$115 Cheap Flights from Key West to Massachusetts in 2026

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.

11:46 am - 4:30 pm

EYW

BDL

4h 44m

1 stop

7:00 am - 12:19 pm

BDL

EYW

5h 19m

1 stop

$208Breeze Airways

Wed, Sep 2 - Mon, Sep 14

11:46 am - 4:30 pm

EYW

BDL

4h 44m

1 stop

6:00 am - 11:06 am

BDL

EYW

5h 06m

1 stop

$214Breeze Airways

Wed, Aug 12 - Wed, Aug 19

11:46 am - 4:30 pm

EYW

BDL

4h 44m

1 stop

6:00 am - 11:06 am

BDL

EYW

5h 06m

1 stop

$221Breeze Airways

Wed, Aug 12 - Wed, Aug 19

3:30 pm - 11:33 pm

EYW

BDL

8h 03m

1 stop

11:12 am - 5:39 pm

BDL

EYW

6h 27m

1 stop

$336American Airlines

Tue, Sep 15 - Fri, Oct 2

3:25 pm - 6:59 pm

EYW

BOS

3h 34mnonstop

5:50 am - 1:47 pm

BOS

EYW

7h 57m

1 stop

$337American Airlines

Tue, Dec 22 - Tue, Dec 29

3:30 pm - 11:33 pm

EYW

BDL

8h 03m

1 stop

11:12 am - 5:39 pm

BDL

EYW

6h 27m

1 stop

$346American Airlines

Tue, Sep 15 - Fri, Oct 2

12:50 pm - 4:39 pm

EYW

BOS

3h 49mnonstop

8:00 am - 11:59 am

BOS

EYW

3h 59mnonstop

$354JetBlue

Sat, Oct 10 - Sat, Oct 17

7:40 am - 2:55 pm

EYW

BOS

7h 15m

1 stop

5:30 am - 1:00 pm

BOS

EYW

7h 30m

1 stop

$484Delta

Thu, Aug 13 - Sun, Aug 16

12:45 pm - 4:15 pm

EYW

BOS

3h 30mnonstop

8:00 am - 11:53 am

BOS

EYW

3h 53mnonstop

$519JetBlue

Thu, Oct 29 - Mon, Nov 2

6:15 pm - 1:25 am

EYW

BOS

7h 10m

1 stop

2:00 pm - 7:57 pm

BOS

EYW

5h 57m

1 stop

$544Delta

Wed, Aug 12 - Sat, Aug 15

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Delta flights from Key West to Massachusetts

Our best Delta deals on Key West to Massachusetts flight tickets

Delta

Aug 13

EYW7:40 amKey West

7h 15m

1 stop

BOS2:55 pmBoston Logan Intl

Aug 16

BOS5:30 amBoston Logan Intl

7h 30m

1 stop

EYW1:00 pmKey West

$484

Delta

Aug 7

EYW7:40 amKey West

7h 15m

1 stop

BOS2:55 pmBoston Logan Intl

Aug 10

BOS8:55 amBoston Logan Intl

8h 25m

1 stop

EYW5:20 pmKey West

$538

Delta

Aug 12

EYW6:15 pmKey West

7h 10m

1 stop

BOS1:25 amBoston Logan Intl

Aug 15

BOS2:00 pmBoston Logan Intl

5h 57m

1 stop

EYW7:57 pmKey West

$544

Allegiant Air flights from Key West to Massachusetts

Our best Allegiant Air deals on Key West to Massachusetts flight tickets

Allegiant Air

Aug 7

EYW10:31 amKey West

22h 34m

1 stop

BOS9:05 amBoston Logan Intl

Aug 9

BOS10:40 amBoston Logan Intl

23h 01m

1 stop

EYW9:41 amKey West

$528

Allegiant Air

Aug 7

EYW10:31 amKey West

22h 34m

1 stop

BOS9:05 amBoston Logan Intl

Aug 9

BOS10:40 amBoston Logan Intl

23h 01m

1 stop

EYW9:41 amKey West

$530

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 9/2

11:46 am-4:30 pm

1 stop4h 44m

Hartford Bradley Intl

Mon 9/14

7:00 am-12:19 pm

1 stop5h 19m

$208

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 8/12

11:46 am-4:30 pm

1 stop4h 44m

Hartford Bradley Intl

Wed 8/19

6:00 am-11:06 am

1 stop5h 06m

$214

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 8/12

11:46 am-4:30 pm

1 stop4h 44m

Hartford Bradley Intl

Wed 8/19

6:00 am-11:06 am

1 stop5h 06m

$221

Key WestHartford

EYW - BDL

EYWBDL

Key West

Tue 9/15

3:30 pm-11:33 pm

1 stop8h 03m

Hartford Bradley Intl

Fri 10/2

11:12 am-5:39 pm

1 stop6h 27m

$336

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 12/22

3:25 pm-6:59 pm

Nonstop3h 34m

Boston Logan Intl

Tue 12/29

5:50 am-1:47 pm

1 stop7h 57m

$337

Key WestHartford

EYW - BDL

EYWBDL

Key West

Tue 9/15

3:30 pm-11:33 pm

1 stop8h 03m

Hartford Bradley Intl

Fri 10/2

11:12 am-5:39 pm

1 stop6h 27m

$346

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 10/10

12:50 pm-4:39 pm

Nonstop3h 49m

Boston Logan Intl

Sat 10/17

8:00 am-11:59 am

Nonstop3h 59m

$354

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 8/13

7:40 am-2:55 pm

1 stop7h 15m

Boston Logan Intl

Sun 8/16

5:30 am-1:00 pm

1 stop7h 30m

$484

Quickest round-trip

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 10/29

12:45 pm-4:15 pm

Nonstop3h 30m

Boston Logan Intl

Mon 11/2

8:00 am-11:53 am

Nonstop3h 53m

$519

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 8/12

6:15 pm-1:25 am

1 stop7h 10m

Boston Logan Intl

Sat 8/15

2:00 pm-7:57 pm

1 stop5h 57m

$544

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 $286. If you aren’t able to travel to Massachusetts during the month of November, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $306.

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 $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

Fastest flight time	3h 34m
Direct flights	Every day
Airports in Massachusetts	140 airports

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

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 3 operators available for flights from Key West Airport to Massachusetts as of August 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 16.67%, Embraer 175 at 16.67%, and Airbus A320-100/200 at 16.67%.

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 $226	Free Cancellation	Rating 7.1 11,846 reviews	Search American Airlines flights
Delta	PriceFrom $239	Free Cancellation	Rating 7.8 8,493 reviews	Search Delta flights
JetBlue	PriceFrom $251	Free Cancellation	Rating 7.1 3,033 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.