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Cheap flights from Massachusetts to Key West from $69

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 5/2. 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
8:05 am - 9:06 am
BDL
-
EYW
25h 01m
1 stop
Breeze Airways Logo
11:46 am - 4:30 pm
EYW
-
BDL
4h 44m
1 stop
$166Breeze Airways
Sat, May 2 - Wed, May 6
Breeze Airways Logo
3:59 pm - 9:06 am
BDL
-
EYW
17h 07m
1 stop
Breeze Airways Logo
11:46 am - 4:30 pm
EYW
-
BDL
4h 44m
1 stop
$175Breeze Airways
Sat, May 2 - Wed, May 6
Breeze Airways Logo
3:59 pm - 9:06 am
BDL
-
EYW
17h 07m
1 stop
Breeze Airways Logo
11:46 am - 4:30 pm
EYW
-
BDL
4h 44m
1 stop
$181Breeze Airways
Sat, May 2 - Wed, May 6
Breeze Airways Logo
3:59 pm - 9:06 am
BDL
-
EYW
17h 07m
1 stop
Breeze Airways Logo
11:46 am - 4:30 pm
EYW
-
BDL
4h 44m
1 stop
$202Breeze Airways
Sat, May 2 - Wed, May 6
Multiple Airlines Logo
7:43 pm - 11:25 am
BDL
-
EYW
15h 42m
1 stop
Multiple Airlines Logo
12:05 pm - 4:45 pm
EYW
-
BDL
28h 40m
1 stop
$215Multiple Airlines
Sat, May 16 - Thu, May 28
American Airlines Logo
2:39 pm - 4:30 pm
ORH
-
EYW
25h 51m
2 stops
American Airlines Logo
11:24 am - 2:14 pm
EYW
-
ORH
26h 50m
2 stops
$247American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
2:39 pm - 10:54 am
ORH
-
EYW
20h 15m
2 stops
American Airlines Logo
5:42 pm - 2:14 pm
EYW
-
ORH
20h 32m
1 stop
$252American Airlines
Sat, May 2 - Wed, May 6
Multiple Airlines Logo
8:02 pm - 12:34 pm
ALB
-
EYW
16h 32m
2 stops
Multiple Airlines Logo
11:07 am - 7:37 pm
EYW
-
ALB
8h 30m
1 stop
$307Multiple Airlines
Mon, Aug 17 - Mon, Aug 24
Allegiant Air Logo
11:28 am - 10:11 am
ALB
-
EYW
22h 43m
2 stops
Allegiant Air Logo
3:08 pm - 11:22 am
EYW
-
ALB
20h 14m
1 stop
$317Allegiant Air
Sun, May 10 - Thu, May 14
Allegiant Air Logo
11:28 am - 10:11 am
ALB
-
EYW
22h 43m
2 stops
Allegiant Air Logo
3:08 pm - 11:22 am
EYW
-
ALB
20h 14m
1 stop
$342Allegiant Air
Sun, May 10 - Thu, May 14

Breeze Airways flights from Massachusetts to Key West

Our best Breeze Airways deals on Massachusetts to Key West flight tickets
Breeze Airways
May 2
BDL8:05 amHartford Bradley Intl
25h 01m
1 stop
EYW9:06 amKey West
May 6
EYW11:46 amKey West
4h 44m
1 stop
BDL4:30 pmHartford Bradley Intl
$166
Breeze Airways
May 2
BDL3:59 pmHartford Bradley Intl
17h 07m
1 stop
EYW9:06 amKey West
May 6
EYW11:46 amKey West
4h 44m
1 stop
BDL4:30 pmHartford Bradley Intl
$175
Breeze Airways
May 2
BDL3:59 pmHartford Bradley Intl
17h 07m
1 stop
EYW9:06 amKey West
May 6
EYW11:46 amKey West
4h 44m
1 stop
BDL4:30 pmHartford Bradley Intl
$181

American Airlines flights from Massachusetts to Key West

Our best American Airlines deals on Massachusetts to Key West flight tickets
American Airlines
May 25
ORH5:18 pmWorcester
20h 23m
1 stop
EYW1:41 pmKey West
May 28
EYW4:44 pmKey West
24h 09m
2 stops
ORH4:53 pmWorcester
$242
American Airlines
May 14
ORH2:39 pmWorcester
25h 51m
2 stops
EYW4:30 pmKey West
May 18
EYW11:24 amKey West
26h 50m
2 stops
ORH2:14 pmWorcester
$247
American Airlines
May 2
ORH2:39 pmWorcester
20h 15m
2 stops
EYW10:54 amKey West
May 6
EYW5:42 pmKey West
20h 32m
1 stop
ORH2:14 pmWorcester
$252

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 April 21, 2026.
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

Cheapest round-trip

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 5/2

8:05 am-9:06 am

1 stop25h 01m

Key West

Wed 5/6

11:46 am-4:30 pm

1 stop4h 44m

$166
Quickest round-trip

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 5/2

3:59 pm-9:06 am

1 stop17h 07m

Key West

Wed 5/6

11:46 am-4:30 pm

1 stop4h 44m

$175

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 5/2

3:59 pm-9:06 am

1 stop17h 07m

Key West

Wed 5/6

11:46 am-4:30 pm

1 stop4h 44m

$181

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 5/2

3:59 pm-9:06 am

1 stop17h 07m

Key West

Wed 5/6

11:46 am-4:30 pm

1 stop4h 44m

$202

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 5/16

7:43 pm-11:25 am

1 stop15h 42m

Key West

Thu 5/28

12:05 pm-4:45 pm

1 stop28h 40m

$215

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Thu 5/14

2:39 pm-4:30 pm

2 stops25h 51m

Key West

Mon 5/18

11:24 am-2:14 pm

2 stops26h 50m

$247

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 5/2

2:39 pm-10:54 am

2 stops20h 15m

Key West

Wed 5/6

5:42 pm-2:14 pm

1 stop20h 32m

$252

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Mon 8/17

8:02 pm-12:34 pm

2 stops16h 32m

Key West

Mon 8/24

11:07 am-7:37 pm

1 stop8h 30m

$307

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sun 5/10

11:28 am-10:11 am

2 stops22h 43m

Key West

Thu 5/14

3:08 pm-11:22 am

1 stop20h 14m

$317

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sun 5/10

11:28 am-10:11 am

2 stops22h 43m

Key West

Thu 5/14

3:08 pm-11:22 am

1 stop20h 14m

$342

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 October is also very affordable. Most momondo users find prices during this month for around $332.

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 Monday. momondo users have found tickets for Monday departures for as low as $380. 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 $556.

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 $409 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 $347 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

$203

Fastest flight time

3h 38m

Direct flights

Mon, Tue, Fri and Sun

Airports in Key West

1 airport
The best one-way flight to Key West from Massachusetts in the past 72 hours is $203. The best round-trip flight deal from Massachusetts to Key West found on momondo in the last 72 hours is $462.
The fastest flight from Massachusetts to Key West takes 3h 38m
Direct flights go from Massachusetts to Key West on Monday, Tuesday, Friday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Key West. From Massachusetts there are direct flights to Key West (EYW).
Search flight deals

Frequently asked questions about flying from Massachusetts to Key West

  • 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 $123Free CancellationRating
6.3
8,629 reviews
Search Spirit Airlines flights
DeltaPriceFrom $148Free CancellationRating
7.9
8,434 reviews
Search Delta flights
United AirlinesPriceFrom $196Free CancellationRating
7.4
9,613 reviews
Search United Airlines flights
JetBluePriceFrom $214Free CancellationRating
7.2
2,949 reviews
Search JetBlue flights
American AirlinesPriceFrom $246Free CancellationRating
7.1
11,645 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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