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Cheap flights from Massachusetts to Key West from $128

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 8/22. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
8:10 am - 11:06 am
BDL
-
EYW
26h 56m
2 stops
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$239Breeze Airways
Tue, Aug 18 - Tue, Aug 25
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
$245Breeze Airways
Mon, Aug 17 - Tue, Aug 25
Multiple Airlines Logo
10:04 am - 11:35 am
BOS
-
EYW
25h 31m
1 stop
Multiple Airlines Logo
11:46 am - 11:50 am
EYW
-
BOS
24h 04m
2 stops
$263Multiple Airlines
Sat, Aug 29 - Wed, Sep 2
Multiple Airlines Logo
11:05 am - 1:38 pm
BOS
-
EYW
26h 33m
1 stop
Multiple Airlines Logo
10:14 am - 8:19 am
EYW
-
BOS
22h 05m
1 stop
$267Multiple Airlines
Sat, Oct 31 - Fri, Nov 6
Allegiant Air Logo
10:32 am - 9:04 am
BOS
-
EYW
22h 32m
1 stop
Allegiant Air Logo
11:09 am - 10:42 am
EYW
-
BOS
23h 33m
1 stop
$278Allegiant Air
Thu, Oct 29 - Mon, Nov 2
Delta Logo
6:15 am - 1:00 pm
ALB
-
EYW
6h 45m
1 stop
Delta Logo
6:15 pm - 11:57 pm
EYW
-
ALB
5h 42m
1 stop
$323Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
2:33 pm - 8:01 pm
ALB
-
EYW
5h 28m
1 stop
Delta Logo
6:19 pm - 11:55 pm
EYW
-
ALB
5h 36m
1 stop
$326Delta
Sat, Sep 26 - Fri, Oct 2
American Airlines Logo
5:23 pm - 1:45 pm
ORH
-
EYW
20h 22m
1 stop
American Airlines Logo
8:09 pm - 4:58 pm
EYW
-
ORH
20h 49m
2 stops
$332American Airlines
Tue, Aug 11 - Mon, Aug 17
American Airlines Logo
5:23 pm - 4:18 pm
ORH
-
EYW
22h 55m
2 stops
American Airlines Logo
8:09 pm - 4:58 pm
EYW
-
ORH
20h 49m
2 stops
$337American Airlines
Tue, Aug 11 - Mon, Aug 17
Allegiant Air Logo
8:02 pm - 10:06 am
ALB
-
EYW
38h 04m
2 stops
Allegiant Air Logo
4:17 pm - 9:55 am
EYW
-
ALB
17h 38m
1 stop
$342Allegiant Air
Fri, Aug 7 - Thu, Aug 13

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Delta flights from Massachusetts to Key West

Our best Delta deals on Massachusetts to Key West flight tickets
Delta
Aug 18
ALB6:15 amAlbany Intl
6h 45m
1 stop
EYW1:00 pmKey West
Aug 25
EYW6:15 pmKey West
5h 42m
1 stop
ALB11:57 pmAlbany Intl
$323
Delta
Sep 26
ALB2:33 pmAlbany Intl
5h 28m
1 stop
EYW8:01 pmKey West
Oct 2
EYW6:19 pmKey West
5h 36m
1 stop
ALB11:55 pmAlbany Intl
$326
Delta
Oct 27
BOS12:45 pmBoston Logan Intl
7h 06m
1 stop
EYW7:51 pmKey West
Nov 6
EYW6:11 pmKey West
6h 47m
1 stop
BOS12:58 amBoston Logan Intl
$327

United Airlines flights from Massachusetts to Key West

Our best United Airlines deals on Massachusetts to Key West flight tickets
United Airlines
Dec 6
BOS6:00 amBoston Logan Intl
9h 06m
2 stops
EYW3:06 pmKey West
Dec 11
EYW4:05 pmKey West
7h 17m
1 stop
BOS11:22 pmBoston Logan Intl
$332
United Airlines
Dec 7
BOS6:00 amBoston Logan Intl
9h 06m
2 stops
EYW3:06 pmKey West
Dec 17
EYW3:04 pmKey West
8h 14m
1 stop
BOS11:18 pmBoston Logan Intl
$343
United Airlines
Jan 5
ALB6:00 amAlbany Intl
9h 06m
2 stops
EYW3:06 pmKey West
Jan 12
EYW6:20 pmKey West
5h 24m
1 stop
ALB11:44 pmAlbany Intl
$353

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 July 17, 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

Tue 8/18

8:10 am-11:06 am

2 stops26h 56m

Key West

Tue 8/25

1:14 pm-4:30 pm

1 stop27h 16m

$239

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 8/17

7:25 am-12:31 pm

1 stop5h 06m

Key West

Tue 8/25

1:14 pm-4:30 pm

1 stop27h 16m

$245

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 8/29

10:04 am-11:35 am

1 stop25h 31m

Key West

Wed 9/2

11:46 am-11:50 am

2 stops24h 04m

$263

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 10/31

11:05 am-1:38 pm

1 stop26h 33m

Key West

Fri 11/6

10:14 am-8:19 am

1 stop22h 05m

$267

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 10/29

10:32 am-9:04 am

1 stop22h 32m

Key West

Mon 11/2

11:09 am-10:42 am

1 stop23h 33m

$278

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Tue 8/18

6:15 am-1:00 pm

1 stop6h 45m

Key West

Tue 8/25

6:15 pm-11:57 pm

1 stop5h 42m

$323
Quickest round-trip

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sat 9/26

2:33 pm-8:01 pm

1 stop5h 28m

Key West

Fri 10/2

6:19 pm-11:55 pm

1 stop5h 36m

$326

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Tue 8/11

5:23 pm-1:45 pm

1 stop20h 22m

Key West

Mon 8/17

8:09 pm-4:58 pm

2 stops20h 49m

$332

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Tue 8/11

5:23 pm-4:18 pm

2 stops22h 55m

Key West

Mon 8/17

8:09 pm-4:58 pm

2 stops20h 49m

$337

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Fri 8/7

8:02 pm-10:06 am

2 stops38h 04m

Key West

Thu 8/13

4:17 pm-9:55 am

1 stop17h 38m

$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, October 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 $113. If you are unable to visit Key West during the month of October, then departing from Massachusetts during the month August is also very affordable. Most momondo users find prices during this month for around $131.

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 $396. 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 $563.

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 from Massachusetts 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 $381 on momondo.

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

There are 4 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

$183

Fastest flight time

3h 53m

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 $183. 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 53m
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

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
DeltaPriceFrom $148Free CancellationRating
7.8
8,476 reviews
Search Delta flights
United AirlinesPriceFrom $196Free CancellationRating
7.4
10,006 reviews
Search United Airlines flights
JetBluePriceFrom $208Free CancellationRating
7.1
3,012 reviews
Search JetBlue flights
American AirlinesPriceFrom $242Free CancellationRating
7.1
11,825 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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