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Cheap flights from Massachusetts to Key West from $113

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 4/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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 - 9:06 am
BDL
-
EYW
17h 07m
1 stop
Breeze Airways Logo
11:46 am - 4:30 pm
EYW
-
BDL
4h 44m
1 stop
$187Breeze Airways
Sat, May 2 - Wed, May 6
Breeze Airways Logo
9:10 am - 11:11 am
BDL
-
EYW
26h 01m
1 stop
Breeze Airways Logo
1:06 pm - 4:20 pm
EYW
-
BDL
27h 14m
1 stop
$191Breeze Airways
Tue, Mar 31 - Mon, Apr 6
Multiple Airlines Logo
3:59 pm - 9:06 am
BDL
-
EYW
17h 07m
1 stop
Multiple Airlines Logo
11:46 am - 12:15 pm
EYW
-
BDL
24h 29m
2 stops
$215Multiple Airlines
Sat, May 2 - Wed, May 6
Multiple Airlines Logo
8:30 am - 5:02 pm
BDL
-
EYW
8h 32m
1 stop
Multiple Airlines Logo
4:22 pm - 10:04 pm
EYW
-
BDL
5h 42m
1 stop
$224Multiple Airlines
Mon, Mar 30 - Thu, Apr 2
Spirit Airlines Logo
5:45 am - 1:37 pm
BOS
-
EYW
7h 52m
1 stop
Spirit Airlines Logo
12:25 pm - 11:59 pm
EYW
-
BOS
11h 34m
1 stop
$235Spirit Airlines
Fri, Apr 10 - Tue, Apr 14
Delta Logo
1:55 pm - 7:45 pm
BOS
-
EYW
5h 50m
1 stop
Delta Logo
7:00 am - 1:54 pm
EYW
-
BOS
6h 54m
1 stop
$237Delta
Tue, Aug 11 - Tue, Aug 18
Spirit Airlines Logo
5:45 am - 1:37 pm
BOS
-
EYW
7h 52m
1 stop
Spirit Airlines Logo
12:25 pm - 11:59 pm
EYW
-
BOS
11h 34m
1 stop
$240Spirit Airlines
Fri, Apr 10 - Tue, Apr 14
American Airlines Logo
2:39 pm - 11:16 am
ORH
-
EYW
20h 37m
2 stops
American Airlines Logo
5:42 pm - 2:14 pm
EYW
-
ORH
20h 32m
1 stop
$242American Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
2:39 pm - 3:40 pm
ORH
-
EYW
25h 01m
2 stops
American Airlines Logo
2:01 pm - 2:14 pm
EYW
-
ORH
24h 13m
2 stops
$247American Airlines
Sun, Apr 12 - Fri, Apr 17
Delta Logo
1:12 pm - 7:41 pm
ALB
-
EYW
6h 29m
1 stop
Delta Logo
6:25 pm - 11:59 pm
EYW
-
ALB
5h 34m
1 stop
$334Delta
Wed, Mar 25 - Wed, Apr 1

Spirit Airlines flights from Massachusetts to Key West

Our best Spirit Airlines deals on Massachusetts to Key West flight tickets
Spirit Airlines
Apr 10
BOS5:45 amBoston Logan Intl
7h 52m
1 stop
EYW1:37 pmKey West
Apr 14
EYW12:25 pmKey West
11h 34m
1 stop
BOS11:59 pmBoston Logan Intl
$235
Spirit Airlines
Apr 10
BOS5:45 amBoston Logan Intl
7h 52m
1 stop
EYW1:37 pmKey West
Apr 14
EYW12:25 pmKey West
11h 34m
1 stop
BOS11:59 pmBoston Logan Intl
$240
Spirit Airlines
Apr 8
BOS5:45 amBoston Logan Intl
5h 45m
1 stop
EYW11:30 amKey West
Apr 14
EYW12:25 pmKey West
11h 34m
1 stop
BOS11:59 pmBoston Logan Intl
$242

Breeze Airways flights from Massachusetts to Key West

Our best Breeze Airways deals on Massachusetts to Key West flight tickets
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
$186
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
$187
Breeze Airways
Mar 31
BDL9:10 amHartford Bradley Intl
26h 01m
1 stop
EYW11:11 amKey West
Apr 6
EYW1:06 pmKey West
27h 14m
1 stop
BDL4:20 pmHartford Bradley Intl
$191

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 February 28, 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

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

$187

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Tue 3/31

9:10 am-11:11 am

1 stop26h 01m

Key West

Mon 4/6

1:06 pm-4:20 pm

1 stop27h 14m

$191

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-12:15 pm

2 stops24h 29m

$215

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 3/30

8:30 am-5:02 pm

1 stop8h 32m

Key West

Thu 4/2

4:22 pm-10:04 pm

1 stop5h 42m

$224

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 4/10

5:45 am-1:37 pm

1 stop7h 52m

Key West

Tue 4/14

12:25 pm-11:59 pm

1 stop11h 34m

$235

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 8/11

1:55 pm-7:45 pm

1 stop5h 50m

Key West

Tue 8/18

7:00 am-1:54 pm

1 stop6h 54m

$237

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 4/10

5:45 am-1:37 pm

1 stop7h 52m

Key West

Tue 4/14

12:25 pm-11:59 pm

1 stop11h 34m

$240

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 5/4

2:39 pm-11:16 am

2 stops20h 37m

Key West

Fri 5/8

5:42 pm-2:14 pm

1 stop20h 32m

$242

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 4/12

2:39 pm-3:40 pm

2 stops25h 01m

Key West

Fri 4/17

2:01 pm-2:14 pm

2 stops24h 13m

$247

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Wed 3/25

1:12 pm-7:41 pm

1 stop6h 29m

Key West

Wed 4/1

6:25 pm-11:59 pm

1 stop5h 34m

$334

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 July is also very affordable. Most momondo users find prices during this month for around $341.

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 $392. 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 $576.

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 $413 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 $363 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

$138

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 $138. The best round-trip flight deal from Massachusetts to Key West found on momondo in the last 72 hours is $397.
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 $95Free CancellationRating
6.3
8,490 reviews
Search Spirit Airlines flights
DeltaPriceFrom $148Free CancellationRating
7.9
8,244 reviews
Search Delta flights
United AirlinesPriceFrom $196Free CancellationRating
7.4
9,370 reviews
Search United Airlines flights
JetBluePriceFrom $221Free CancellationRating
7.2
2,895 reviews
Search JetBlue flights
American AirlinesPriceFrom $246Free CancellationRating
7.1
11,370 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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