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Cheap flights from Key West to Boston from $141

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Boston departing on 3/26. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:32 pm - 9:07 am
EYW
-
PWM
16h 35m
1 stop
Multiple Airlines Logo
6:18 pm - 9:42 pm
PWM
-
EYW
27h 24m
1 stop
$292Multiple Airlines
Thu, Apr 2 - Sat, Apr 4
Multiple Airlines Logo
4:32 pm - 9:07 am
EYW
-
PWM
16h 35m
1 stop
Multiple Airlines Logo
6:18 pm - 3:42 pm
PWM
-
EYW
21h 24m
1 stop
$325Multiple Airlines
Thu, Apr 2 - Wed, Apr 8
Breeze Airways Logo
9:46 am - 9:07 am
EYW
-
PWM
23h 21m
1 stop
Breeze Airways Logo
5:06 pm - 12:21 pm
PWM
-
EYW
19h 15m
2 stops
$335Breeze Airways
Thu, Apr 2 - Mon, Apr 6
United Airlines Logo
5:30 pm - 11:04 pm
EYW
-
PWM
5h 34m
1 stop
United Airlines Logo
6:00 am - 1:23 pm
PWM
-
EYW
7h 23m
1 stop
$339United Airlines
Wed, Mar 11 - Sun, Mar 15
Delta Logo
2:40 pm - 11:22 pm
EYW
-
PWM
8h 42m
1 stop
Delta Logo
6:03 am - 12:42 pm
PWM
-
EYW
6h 39m
1 stop
$357Delta
Wed, Apr 1 - Wed, Apr 8
Delta Logo
2:40 pm - 11:22 pm
EYW
-
PWM
8h 42m
1 stop
Delta Logo
6:03 am - 12:42 pm
PWM
-
EYW
6h 39m
1 stop
$362Delta
Thu, Apr 2 - Tue, Apr 7
Multiple Airlines Logo
12:25 pm - 10:17 am
EYW
-
PWM
21h 52m
2 stops
Multiple Airlines Logo
6:18 pm - 9:42 pm
PWM
-
EYW
27h 24m
1 stop
$370Multiple Airlines
Tue, Mar 31 - Sat, Apr 4
Breeze Airways Logo
9:46 am - 10:49 am
EYW
-
PWM
25h 03m
2 stops
Breeze Airways Logo
6:18 pm - 10:21 am
PWM
-
EYW
16h 03m
1 stop
$372Breeze Airways
Thu, Apr 2 - Sat, Apr 4
Multiple Airlines Logo
1:06 pm - 10:17 am
EYW
-
PWM
21h 11m
1 stop
Multiple Airlines Logo
6:18 pm - 9:42 pm
PWM
-
EYW
27h 24m
1 stop
$375Multiple Airlines
Fri, Apr 3 - Sat, Apr 4
United Airlines Logo
2:24 pm - 10:51 pm
EYW
-
PWM
8h 27m
1 stop
United Airlines Logo
6:04 am - 2:51 pm
PWM
-
EYW
8h 47m
1 stop
$388United Airlines
Thu, Mar 26 - Thu, Apr 2

American Airlines flights from Key West to Portland, Maine

Our best American Airlines deals on Key West to Portland, Maine flight tickets
American Airlines
Mar 4
EYW5:19 pmKey West
6h 31m
1 stop
PWM11:50 pmPortland
Mar 11
PWM6:00 amPortland
6h 00m
1 stop
EYW12:00 pmKey West
$327
American Airlines
Mar 4
EYW3:51 pmKey West
7h 59m
2 stops
PWM11:50 pmPortland
Mar 11
PWM6:00 amPortland
6h 00m
1 stop
EYW12:00 pmKey West
$332
American Airlines
Mar 4
EYW5:19 pmKey West
6h 31m
1 stop
PWM11:50 pmPortland
Mar 11
PWM7:10 amPortland
12h 02m
2 stops
EYW7:12 pmKey West
$378

Breeze Airways flights from Key West to Portland, Maine

Our best Breeze Airways deals on Key West to Portland, Maine flight tickets
Breeze Airways
Apr 2
EYW9:46 amKey West
23h 21m
1 stop
PWM9:07 amPortland
Apr 6
PWM5:06 pmPortland
19h 15m
2 stops
EYW12:21 pmKey West
$335
Breeze Airways
Apr 2
EYW9:46 amKey West
25h 03m
2 stops
PWM10:49 amPortland
Apr 4
PWM6:18 pmPortland
16h 03m
1 stop
EYW10:21 amKey West
$372
Breeze Airways
Apr 5
EYW9:46 amKey West
23h 21m
1 stop
PWM9:07 amPortland
Apr 8
PWM6:18 pmPortland
21h 24m
1 stop
EYW3:42 pmKey West
$391

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Portland, Maine 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 Key West to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

4:32 pm-9:07 am

1 stop16h 35m

Portland

Sat 4/4

6:18 pm-9:42 pm

1 stop27h 24m

$292

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

4:32 pm-9:07 am

1 stop16h 35m

Portland

Wed 4/8

6:18 pm-3:42 pm

1 stop21h 24m

$325

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

9:46 am-9:07 am

1 stop23h 21m

Portland

Mon 4/6

5:06 pm-12:21 pm

2 stops19h 15m

$335

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 3/11

5:30 pm-11:04 pm

1 stop5h 34m

Portland

Sun 3/15

6:00 am-1:23 pm

1 stop7h 23m

$339

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 4/1

2:40 pm-11:22 pm

1 stop8h 42m

Portland

Wed 4/8

6:03 am-12:42 pm

1 stop6h 39m

$357

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

2:40 pm-11:22 pm

1 stop8h 42m

Portland

Tue 4/7

6:03 am-12:42 pm

1 stop6h 39m

$362

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 3/31

12:25 pm-10:17 am

2 stops21h 52m

Portland

Sat 4/4

6:18 pm-9:42 pm

1 stop27h 24m

$370

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

9:46 am-10:49 am

2 stops25h 03m

Portland

Sat 4/4

6:18 pm-10:21 am

1 stop16h 03m

$372

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 4/3

1:06 pm-10:17 am

1 stop21h 11m

Portland

Sat 4/4

6:18 pm-9:42 pm

1 stop27h 24m

$375

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 3/26

2:24 pm-10:51 pm

1 stop8h 27m

Portland

Thu 4/2

6:04 am-2:51 pm

1 stop8h 47m

$388

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 Boston from

How to get the cheapest flight ticket from Key West to Portland, Maine

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 airline that flies from Key West to Portland?

Breeze Airways and Delta are the most popular carriers operating from Key West to Portland

What airlines fly to Portland, Maine?

American Airlines, JetBlue and Delta are the top three most popular airlines that fly to Portland, Maine from Key West according to our data. American Airlines is the first choice among our users, with 71% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 3 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

When to book flights from Key West to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Key West to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Key West to Portland, Maine (EYW to PWM) flight deals and tips

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

Fastest flight time

6h 28m

Direct flights

None
The fastest flight from Key West to Portland, Maine takes 6h 28m
There are no direct flights from Key West to Portland, Maine. There are no popular flight routes from Key West to Portland, Maine.
Search flight deals

  • How far is Key West to Portland by plane?

    The straight-line distance from Key West to Portland is 1471.7 mi. In terms of flight time, this usually takes a little over 6h 28m.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Key West Airport to Portland Airport.

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

    The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Key West to Portland, Maine?

Best airlines flying from Key West to Portland, Maine

Compare and see reviews for airlines that fly from Key West to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $268Free CancellationRating
7.1
11,367 reviews
Search American Airlines flights
DeltaPriceFrom $274Free CancellationRating
7.9
8,245 reviews
Search Delta flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
Oxford
Georgetown
Falmouth
Tamworth

Why use momondo?

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

It is quick and easy to find Key West to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

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

Yes. momondo allows you to filter the results for Key West to Portland flights to just show those with flexible booking policies.

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

momondo helps you find the best flight between Key West and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Portland from Key West 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 Portland, Maine trip

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