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Cheap flights from Massachusetts to Key West from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Key West departing on 1/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Massachusetts to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Breeze Airways Logo
3:59 pm - 9:26 am
BDL
-
EYW
17h 27m1 stop
Breeze Airways Logo
10:06 am - 11:56 pm
EYW
-
BDL
13h 50m2 stops
$181Breeze Airways
Sat, Jan 24 - Thu, Jan 29
Breeze Airways Logo
3:00 pm - 9:09 am
BDL
-
EYW
18h 09m1 stop
Breeze Airways Logo
1:06 pm - 3:05 pm
EYW
-
BDL
25h 59m1 stop
$185Breeze Airways
Sun, Jan 25 - Fri, Jan 30
American Airlines Logo
1:40 pm - 1:06 pm
ORH
-
EYW
23h 26m2 stops
American Airlines Logo
5:10 pm - 1:15 pm
EYW
-
ORH
20h 05m1 stop
$202American Airlines
Wed, Feb 18 - Thu, Feb 26
American Airlines Logo
2:23 pm - 1:03 pm
ORH
-
EYW
22h 40m2 stops
American Airlines Logo
4:04 pm - 1:53 pm
EYW
-
ORH
21h 49m2 stops
$207American Airlines
Sat, Jan 31 - Wed, Feb 4
Multiple Airlines Logo
8:15 pm - 9:26 am
BDL
-
EYW
13h 11m1 stop
Multiple Airlines Logo
10:49 am - 11:56 pm
EYW
-
BDL
37h 07m2 stops
$213Multiple Airlines
Sat, Jan 17 - Wed, Jan 21
Multiple Airlines Logo
11:30 am - 10:21 am
ALB
-
EYW
22h 51m1 stop
Multiple Airlines Logo
12:15 pm - 10:32 am
EYW
-
ALB
22h 17m1 stop
$244Multiple Airlines
Sat, Feb 21 - Thu, Feb 26
Spirit Airlines Logo
5:45 am - 1:30 pm
BOS
-
EYW
7h 45m1 stop
Spirit Airlines Logo
2:25 pm - 2:38 pm
EYW
-
BOS
24h 13m3 stops
$263Spirit Airlines
Wed, Jan 7 - Fri, Jan 9
Spirit Airlines Logo
5:34 am - 11:56 am
BOS
-
EYW
6h 22m1 stop
Spirit Airlines Logo
2:25 pm - 5:44 pm
EYW
-
BOS
27h 19m3 stops
$264Spirit Airlines
Thu, Jan 8 - Mon, Jan 12
JetBlue Logo
8:09 am - 12:05 pm
BOS
-
EYW
3h 56mnonstop
JetBlue Logo
1:00 pm - 4:36 pm
EYW
-
BOS
3h 36mnonstop
$267JetBlue
Sun, Feb 1 - Thu, Feb 5
JetBlue Logo
8:09 am - 12:05 pm
BOS
-
EYW
3h 56mnonstop
JetBlue Logo
1:05 pm - 4:40 pm
EYW
-
BOS
3h 35mnonstop
$273JetBlue
Tue, Feb 3 - Fri, Feb 6

American Airlines flights from Massachusetts to Key West

Our best American Airlines deals on Massachusetts to Key West flight tickets
American Airlines
Feb 18
ORH1:40 pmWorcester
23h 26m
2 stops
EYW1:06 pmKey West
Feb 26
EYW5:10 pmKey West
20h 05m
1 stop
ORH1:15 pmWorcester
$202
Find similar
American Airlines
Jan 31
ORH2:23 pmWorcester
22h 40m
2 stops
EYW1:03 pmKey West
Feb 4
EYW4:04 pmKey West
21h 49m
2 stops
ORH1:53 pmWorcester
$207
Find similar
American Airlines
Jan 17
BDL1:24 pmHartford Bradley Intl
10h 32m
2 stops
EYW11:56 pmKey West
Jan 21
EYW7:08 amKey West
8h 39m
2 stops
BDL3:47 pmHartford Bradley Intl
$264
Find similar

Spirit Airlines flights from Massachusetts to Key West

Our best Spirit Airlines deals on Massachusetts to Key West flight tickets
Spirit Airlines
Jan 7
BOS5:45 amBoston Logan Intl
7h 45m
1 stop
EYW1:30 pmKey West
Jan 9
EYW2:25 pmKey West
24h 13m
3 stops
BOS2:38 pmBoston Logan Intl
$263
Find similar
Spirit Airlines
Jan 8
BOS5:34 amBoston Logan Intl
6h 22m
1 stop
EYW11:56 amKey West
Jan 12
EYW2:25 pmKey West
27h 19m
3 stops
BOS5:44 pmBoston Logan Intl
$264
Find similar
Spirit Airlines
Jan 16
BOS5:34 amBoston Logan Intl
7h 56m
1 stop
EYW1:30 pmKey West
Jan 18
EYW12:51 pmKey West
11h 06m
1 stop
BOS11:57 pmBoston Logan Intl
$265
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Key West 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, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Massachusetts to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 1/24

3:59 pm-9:26 am

1 stop17h 27m

Key West

Thu 1/29

10:06 am-11:56 pm

2 stops13h 50m

$181

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sun 1/25

3:00 pm-9:09 am

1 stop18h 09m

Key West

Fri 1/30

1:06 pm-3:05 pm

1 stop25h 59m

$185

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Wed 2/18

1:40 pm-1:06 pm

2 stops23h 26m

Key West

Thu 2/26

5:10 pm-1:15 pm

1 stop20h 05m

$202

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 1/31

2:23 pm-1:03 pm

2 stops22h 40m

Key West

Wed 2/4

4:04 pm-1:53 pm

2 stops21h 49m

$207

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 1/17

8:15 pm-9:26 am

1 stop13h 11m

Key West

Wed 1/21

10:49 am-11:56 pm

2 stops37h 07m

$213

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sat 2/21

11:30 am-10:21 am

1 stop22h 51m

Key West

Thu 2/26

12:15 pm-10:32 am

1 stop22h 17m

$244

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 1/7

5:45 am-1:30 pm

1 stop7h 45m

Key West

Fri 1/9

2:25 pm-2:38 pm

3 stops24h 13m

$263

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 1/8

5:34 am-11:56 am

1 stop6h 22m

Key West

Mon 1/12

2:25 pm-5:44 pm

3 stops27h 19m

$264

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sun 2/1

8:09 am-12:05 pm

Nonstop3h 56m

Key West

Thu 2/5

1:00 pm-4:36 pm

Nonstop3h 36m

$267

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 2/3

8:09 am-12:05 pm

Nonstop3h 56m

Key West

Fri 2/6

1:05 pm-4:40 pm

Nonstop3h 35m

$273

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Key West from

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

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

What is the cheapest month to fly to Key West?

In general, September is the cheapest month to fly from Massachusetts to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $316. If you are unable to visit Key West during the month of September, then departing from Massachusetts during the month August is also very affordable. Most momondo users find prices during this month for around $351.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Massachusetts is on a Sunday. momondo users have found tickets for Sunday departures for as low as $439. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Key West for around $617.

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

According to our data, the cheapest time of day to fly to Key West is at noon. momondo users have found flights departing from Massachusetts to Key West at noon for as low as $415. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the morning, with an average ticket price of $498. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Massachusetts to Key West flight route?

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

How far in advance should I book a flight to Key West?

You are more likely to see cheaper flights to Key West from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $419 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Massachusetts for as low as $369 on momondo.

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

There are 3 cabin classes available to choose from on Massachusetts to Key West 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 Massachusetts to Key West flights?

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

Cheap Massachusetts to Key West flight deals and tips

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

Best Price Found

$201

Fastest flight time

3h 38m

Direct flights

Every day

Airports in Key West

1 airport
The best one-way flight to Key West from Massachusetts in the past 72 hours is $201. The best round-trip flight deal from Massachusetts to Key West found on momondo in the last 72 hours is $332.
The fastest flight from Massachusetts to Key West takes 3h 38m
Direct flights go from Massachusetts to Key West every day.
There is 1 airport in Key West. From Massachusetts there are direct flights to Key West (EYW).
Search flight deals

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

    Prices for flights from Massachusetts to Key West Airport refresh daily.

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

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

    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 Massachusetts to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Massachusetts to Key West?

Best airlines flying from Massachusetts to Key West

Compare and see reviews for airlines that fly from Massachusetts to Key West with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $66Free CancellationRating
6.3
8,179 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
DeltaPriceFrom $168Free CancellationRating
7.9
8,008 reviews
Search Delta flights
JetBluePriceFrom $244Free CancellationRating
7.2
2,899 reviews
Search JetBlue flights
American AirlinesPriceFrom $249Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

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

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

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

Yes. momondo enables you to select and highlight flights to Key West from Massachusetts with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Key West from Massachusetts.

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

Price alerts on flights to Key West from Massachusetts are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Key West trip

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