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Cheap flights from Portland, Maine to Key West from $178

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Key West departing on 2/21. 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 Portland, Maine to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 11:26 am
PWM
-
EYW
5h 26m
1 stop
American Airlines Logo
3:56 pm - 11:55 pm
EYW
-
PWM
7h 59m
2 stops
$262American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
6:00 am - 4:49 pm
PWM
-
EYW
10h 49m
2 stops
American Airlines Logo
3:56 pm - 11:55 pm
EYW
-
PWM
7h 59m
2 stops
$267American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
6:00 am - 11:32 am
PWM
-
EYW
5h 32m
1 stop
American Airlines Logo
5:19 pm - 11:55 pm
EYW
-
PWM
6h 36m
1 stop
$290American Airlines
Wed, Mar 4 - Tue, Mar 17
American Airlines Logo
6:00 am - 11:26 am
PWM
-
EYW
5h 26m
1 stop
American Airlines Logo
5:19 pm - 11:55 pm
EYW
-
PWM
6h 36m
1 stop
$323American Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
7:00 am - 2:05 pm
PWM
-
EYW
7h 05m
1 stop
American Airlines Logo
5:04 pm - 10:59 pm
EYW
-
PWM
5h 55m
1 stop
$327American Airlines
Tue, Feb 24 - Wed, Mar 4
American Airlines Logo
6:00 am - 11:32 am
PWM
-
EYW
5h 32m
1 stop
American Airlines Logo
3:56 pm - 11:55 pm
EYW
-
PWM
7h 59m
2 stops
$328American Airlines
Wed, Mar 4 - Tue, Mar 17
American Airlines Logo
7:00 am - 3:57 pm
PWM
-
EYW
8h 57m
2 stops
American Airlines Logo
5:04 pm - 10:59 pm
EYW
-
PWM
5h 55m
1 stop
$332American Airlines
Tue, Feb 24 - Wed, Mar 4
American Airlines Logo
12:29 pm - 10:22 pm
PWM
-
EYW
9h 53m
2 stops
American Airlines Logo
3:56 pm - 11:55 pm
EYW
-
PWM
7h 59m
2 stops
$334American Airlines
Wed, Mar 4 - Tue, Mar 17
American Airlines Logo
6:00 am - 11:32 am
PWM
-
EYW
5h 32m
1 stop
American Airlines Logo
5:19 pm - 11:55 pm
EYW
-
PWM
6h 36m
1 stop
$336American Airlines
Wed, Mar 4 - Tue, Mar 17
American Airlines Logo
7:00 am - 4:49 pm
PWM
-
EYW
9h 49m
2 stops
American Airlines Logo
1:55 pm - 11:50 pm
EYW
-
PWM
9h 55m
2 stops
$338American Airlines
Tue, Feb 24 - Wed, Mar 4

American Airlines flights from Portland, Maine to Key West

Our best American Airlines deals on Portland, Maine to Key West flight tickets
American Airlines
Mar 10
PWM6:00 amPortland
5h 26m
1 stop
EYW11:26 amKey West
Mar 17
EYW3:56 pmKey West
7h 59m
2 stops
PWM11:55 pmPortland
$262
American Airlines
Mar 10
PWM6:00 amPortland
10h 49m
2 stops
EYW4:49 pmKey West
Mar 17
EYW3:56 pmKey West
7h 59m
2 stops
PWM11:55 pmPortland
$267
American Airlines
Mar 4
PWM6:00 amPortland
5h 32m
1 stop
EYW11:32 amKey West
Mar 17
EYW5:19 pmKey West
6h 36m
1 stop
PWM11:55 pmPortland
$290

Breeze Airways flights from Portland, Maine to Key West

Our best Breeze Airways deals on Portland, Maine to Key West flight tickets
Breeze Airways
Feb 21
PWM6:18 pmPortland
16h 03m
1 stop
EYW10:21 amKey West
Feb 26
EYW9:46 amKey West
23h 21m
1 stop
PWM9:07 amPortland
$380
Breeze Airways
Feb 21
PWM6:18 pmPortland
16h 03m
1 stop
EYW10:21 amKey West
Feb 26
EYW9:46 amKey West
25h 03m
2 stops
PWM10:49 amPortland
$389
Breeze Airways
Feb 28
PWM6:18 pmPortland
16h 03m
1 stop
EYW10:21 amKey West
Mar 11
EYW11:51 amKey West
46h 58m
2 stops
PWM10:49 amPortland
$397

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine 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 14, 2026.
Use the filters below to find and compare flights from Portland, Maine to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/10

6:00 am-11:26 am

1 stop5h 26m

Key West

Tue 3/17

3:56 pm-11:55 pm

2 stops7h 59m

$262

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/10

6:00 am-4:49 pm

2 stops10h 49m

Key West

Tue 3/17

3:56 pm-11:55 pm

2 stops7h 59m

$267

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 3/4

6:00 am-11:32 am

1 stop5h 32m

Key West

Tue 3/17

5:19 pm-11:55 pm

1 stop6h 36m

$290

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/10

6:00 am-11:26 am

1 stop5h 26m

Key West

Tue 3/17

5:19 pm-11:55 pm

1 stop6h 36m

$323

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 2/24

7:00 am-2:05 pm

1 stop7h 05m

Key West

Wed 3/4

5:04 pm-10:59 pm

1 stop5h 55m

$327

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 3/4

6:00 am-11:32 am

1 stop5h 32m

Key West

Tue 3/17

3:56 pm-11:55 pm

2 stops7h 59m

$328

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 2/24

7:00 am-3:57 pm

2 stops8h 57m

Key West

Wed 3/4

5:04 pm-10:59 pm

1 stop5h 55m

$332

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 3/4

12:29 pm-10:22 pm

2 stops9h 53m

Key West

Tue 3/17

3:56 pm-11:55 pm

2 stops7h 59m

$334

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 3/4

6:00 am-11:32 am

1 stop5h 32m

Key West

Tue 3/17

5:19 pm-11:55 pm

1 stop6h 36m

$336

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 2/24

7:00 am-4:49 pm

2 stops9h 49m

Key West

Wed 3/4

1:55 pm-11:50 pm

2 stops9h 55m

$338

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 Portland, Maine 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, June is the cheapest month to fly from Portland, Maine to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $308. If you are unable to visit Key West during the month of June, then departing from Portland, Maine during the month August is also very affordable. Most momondo users find prices during this month for around $352.

How far in advance should I book a flight to Key West?

You are more likely to see cheaper flights to Key West from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $433 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Portland, Maine for as low as $256 on momondo.

When to book flights from Portland, Maine to Key West

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

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

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

Fastest flight time

6h 42m

Direct flights

None
The fastest flight from Portland, Maine to Key West takes 6h 42m
There are no direct flights from Portland, Maine to Key West. There are no popular flight routes from Portland, Maine to Key West.
Search flight deals

  • How far is Portland to Key West by plane?

    A flight from Portland to Key West will travel around 1471.7 mi. Typically, this will take 6h 42m by plane in normal conditions.

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

    Prices for flights from Portland Airport to Key West Airport are updated daily.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Key West Airport.

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

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Portland, Maine to Key West

Compare and see reviews for airlines that fly from Portland, Maine to Key West with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $256Free CancellationRating
7.4
9,289 reviews
Search United Airlines flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,203 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
11,288 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 Portland to Key West?

Finding the right flight to Key West from Portland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Key West quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Key West from Portland which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Portland to Key West flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Portland and alert you when they change.

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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