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Cheap flights from Massachusetts to Key West from $104

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 11/15. 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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Cheap round-trip flights

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JetBlue Logo
8:00 am - 11:53 amBOS-EYW
3h 53mnonstop
JetBlue Logo
12:49 pm - 4:20 pmEYW-BOS
3h 31mnonstop
$215JetBlue
Find Deal
Mon, Nov 17 - Wed, Nov 26
JetBlue Logo
8:00 am - 11:53 amBOS-EYW
3h 53mnonstop
JetBlue Logo
12:45 pm - 4:15 pmEYW-BOS
3h 30mnonstop
$217JetBlue
Find Deal
Mon, Oct 27 - Thu, Oct 30
Spirit Airlines Logo
5:45 am - 1:30 pmBOS-EYW
7h 45m1 stop
Spirit Airlines Logo
2:25 pm - 12:40 amEYW-BOS
10h 15m1 stop
$223Spirit Airlines
Find Deal
Thu, Jan 22 - Tue, Jan 27
Delta Logo
5:40 am - 11:31 amBOS-EYW
5h 51m1 stop
Delta Logo
6:18 pm - 1:26 amEYW-BOS
7h 08m1 stop
$227Delta
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Mon, Nov 10 - Wed, Nov 19
Spirit Airlines Logo
5:50 am - 11:20 amBOS-EYW
5h 30m1 stop
Spirit Airlines Logo
12:20 pm - 11:57 pmEYW-BOS
11h 37m1 stop
$228Spirit Airlines
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Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
6:17 am - 2:40 pmBOS-EYW
32h 23m2 stops
Multiple Airlines Logo
3:23 pm - 8:28 amEYW-BOS
17h 05m1 stop
$230Multiple Airlines
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Sat, Oct 25 - Thu, Oct 30
Multiple Airlines Logo
11:13 am - 3:33 pmBDL-EYW
28h 20m2 stops
Multiple Airlines Logo
9:36 pm - 12:41 pmEYW-BDL
15h 05m1 stop
$231Multiple Airlines
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Sat, Nov 1 - Thu, Nov 6
United Airlines Logo
6:00 am - 1:52 pmBOS-EYW
7h 52m1 stop
United Airlines Logo
2:48 pm - 10:48 pmEYW-BOS
8h 00m1 stop
$232United Airlines
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Mon, Oct 27 - Thu, Oct 30
Delta Logo
12:10 pm - 8:06 pmBOS-EYW
7h 56m1 stop
Delta Logo
6:17 pm - 1:13 amEYW-BOS
6h 56m1 stop
$237Delta
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Thu, Oct 30 - Thu, Nov 6
United Airlines Logo
6:00 am - 1:52 pmBOS-EYW
7h 52m1 stop
United Airlines Logo
2:48 pm - 11:42 pmEYW-BOS
8h 54m2 stops
$238United Airlines
Find Deal
Mon, Oct 27 - Thu, Oct 30

JetBlue flights from Massachusetts to Key West

Our best JetBlue deals on Massachusetts to Key West flight tickets
JetBlue
Nov 17
BOS8:00 amBoston Logan Intl
3h 53m
EYW11:53 amKey West
Nov 26
EYW12:49 pmKey West
3h 31m
BOS4:20 pmBoston Logan Intl
$215
Find similar
JetBlue
Oct 27
BOS8:00 amBoston Logan Intl
3h 53m
EYW11:53 amKey West
Oct 30
EYW12:45 pmKey West
3h 30m
BOS4:15 pmBoston Logan Intl
$217
Find similar
JetBlue
Nov 17
BOS8:00 amBoston Logan Intl
3h 53m
EYW11:53 amKey West
Nov 26
EYW12:49 pmKey West
3h 31m
BOS4:20 pmBoston Logan Intl
$218
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 22
BOS5:45 amBoston Logan Intl
7h 45m
1 stop
EYW1:30 pmKey West
Jan 27
EYW2:25 pmKey West
10h 15m
1 stop
BOS12:40 amBoston Logan Intl
$223
Find similar
Spirit Airlines
Dec 11
BOS5:50 amBoston Logan Intl
5h 30m
1 stop
EYW11:20 amKey West
Dec 14
EYW12:20 pmKey West
11h 37m
1 stop
BOS11:57 pmBoston Logan Intl
$228
Find similar
Spirit Airlines
Feb 18
BOS9:48 pmBoston Logan Intl
15h 42m
1 stop
EYW1:30 pmKey West
Feb 25
EYW2:25 pmKey West
10h 15m
1 stop
BOS12:40 amBoston Logan Intl
$266
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 October 14, 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

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 11/17

8:00 am-11:53 am

Nonstop3h 53m

Key West

Wed 11/26

12:49 pm-4:20 pm

Nonstop3h 31m

$215

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 10/27

8:00 am-11:53 am

Nonstop3h 53m

Key West

Thu 10/30

12:45 pm-4:15 pm

Nonstop3h 30m

$217

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 1/22

5:45 am-1:30 pm

1 stop7h 45m

Key West

Tue 1/27

2:25 pm-12:40 am

1 stop10h 15m

$223

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 11/10

5:40 am-11:31 am

1 stop5h 51m

Key West

Wed 11/19

6:18 pm-1:26 am

1 stop7h 08m

$227

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 12/11

5:50 am-11:20 am

1 stop5h 30m

Key West

Sun 12/14

12:20 pm-11:57 pm

1 stop11h 37m

$228

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 10/25

6:17 am-2:40 pm

2 stops32h 23m

Key West

Thu 10/30

3:23 pm-8:28 am

1 stop17h 05m

$230

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 11/1

11:13 am-3:33 pm

2 stops28h 20m

Key West

Thu 11/6

9:36 pm-12:41 pm

1 stop15h 05m

$231

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 10/27

6:00 am-1:52 pm

1 stop7h 52m

Key West

Thu 10/30

2:48 pm-10:48 pm

1 stop8h 00m

$232

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 10/30

12:10 pm-8:06 pm

1 stop7h 56m

Key West

Thu 11/6

6:17 pm-1:13 am

1 stop6h 56m

$237

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 10/27

6:00 am-1:52 pm

1 stop7h 52m

Key West

Thu 10/30

2:48 pm-11:42 pm

2 stops8h 54m

$238

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 $432. 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 $660.

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 $443. 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 $494. 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 $414 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 $355 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?

You could potentially save up to 6% on your flight if you consider stops on a Massachusetts to Key West flight.

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

$158

Fastest flight time

3h 52m

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 $158. The best round-trip flight deal from Massachusetts to Key West found on momondo in the last 72 hours is $297.
The fastest flight from Massachusetts to Key West takes 3h 52m
Direct flights go from Massachusetts to Key West every day.
There is 1 airport near Key West: 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
8,096 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $135Free CancellationRating
7.4
8,976 reviews
Search United Airlines flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,975 reviews
Search Delta flights
JetBluePriceFrom $216Free CancellationRating
7.2
2,906 reviews
Search JetBlue flights
American AirlinesPriceFrom $248Free CancellationRating
7.2
11,042 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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