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Cheap flights from Portland, Maine to Key West from $127

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 5/2. 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

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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.
Breeze Airways Logo
6:18 pm - 10:21 am
PWM
-
EYW
16h 03m
1 stop
Breeze Airways Logo
11:46 am - 7:16 pm
EYW
-
PWM
31h 30m
2 stops
$286Breeze Airways
Sat, May 2 - Wed, May 6
Breeze Airways Logo
6:18 pm - 10:21 am
PWM
-
EYW
16h 03m
1 stop
Breeze Airways Logo
11:46 am - 7:16 pm
EYW
-
PWM
31h 30m
2 stops
$289Breeze Airways
Sat, May 2 - Wed, May 6
American Airlines Logo
11:24 am - 10:36 pm
PWM
-
EYW
11h 12m
2 stops
American Airlines Logo
4:20 pm - 10:46 pm
EYW
-
PWM
6h 26m
1 stop
$296American Airlines
Sat, May 9 - Wed, May 13
Breeze Airways Logo
6:26 pm - 10:24 am
PWM
-
EYW
15h 58m
1 stop
Breeze Airways Logo
12:07 pm - 9:12 am
EYW
-
PWM
21h 05m
1 stop
$299Breeze Airways
Sat, Jun 6 - Fri, Jun 12
United Airlines Logo
5:30 am - 3:07 pm
PWM
-
EYW
9h 37m
2 stops
United Airlines Logo
2:49 pm - 11:59 pm
EYW
-
PWM
9h 10m
2 stops
$301United Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
6:00 am - 1:49 pm
PWM
-
EYW
7h 49m
1 stop
American Airlines Logo
5:37 pm - 11:51 pm
EYW
-
PWM
6h 14m
1 stop
$302American Airlines
Sun, May 17 - Tue, May 26
American Airlines Logo
6:00 am - 11:29 am
PWM
-
EYW
5h 29m
1 stop
American Airlines Logo
11:24 am - 11:26 pm
EYW
-
PWM
12h 02m
2 stops
$309American Airlines
Sat, May 9 - Wed, May 13
Breeze Airways Logo
5:01 pm - 11:25 am
PWM
-
EYW
18h 24m
2 stops
Breeze Airways Logo
12:07 pm - 9:12 am
EYW
-
PWM
21h 05m
1 stop
$310Breeze Airways
Sat, Jun 6 - Fri, Jun 12
American Airlines Logo
6:00 am - 11:29 am
PWM
-
EYW
5h 29m
1 stop
American Airlines Logo
4:20 pm - 10:46 pm
EYW
-
PWM
6h 26m
1 stop
$317American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
6:00 am - 11:29 am
PWM
-
EYW
5h 29m
1 stop
American Airlines Logo
4:20 pm - 10:46 pm
EYW
-
PWM
6h 26m
1 stop
$341American Airlines
Sat, May 9 - Wed, May 13

American Airlines flights from Portland, Maine to Key West

Our best American Airlines deals on Portland, Maine to Key West flight tickets
American Airlines
May 9
PWM11:24 amPortland
11h 12m
2 stops
EYW10:36 pmKey West
May 13
EYW4:20 pmKey West
6h 26m
1 stop
PWM10:46 pmPortland
$296
American Airlines
May 17
PWM6:00 amPortland
7h 49m
1 stop
EYW1:49 pmKey West
May 26
EYW5:37 pmKey West
6h 14m
1 stop
PWM11:51 pmPortland
$302
American Airlines
May 9
PWM6:00 amPortland
5h 29m
1 stop
EYW11:29 amKey West
May 13
EYW11:24 amKey West
12h 02m
2 stops
PWM11:26 pmPortland
$309

Breeze Airways flights from Portland, Maine to Key West

Our best Breeze Airways deals on Portland, Maine to Key West flight tickets
Breeze Airways
May 2
PWM6:18 pmPortland
16h 03m
1 stop
EYW10:21 amKey West
May 6
EYW11:46 amKey West
31h 30m
2 stops
PWM7:16 pmPortland
$286
Breeze Airways
May 2
PWM6:18 pmPortland
16h 03m
1 stop
EYW10:21 amKey West
May 6
EYW11:46 amKey West
31h 30m
2 stops
PWM7:16 pmPortland
$289
Breeze Airways
Jun 6
PWM6:26 pmPortland
15h 58m
1 stop
EYW10:24 amKey West
Jun 12
EYW12:07 pmKey West
21h 05m
1 stop
PWM9:12 amPortland
$299

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 April 1, 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

Cheapest round-trip

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/2

6:18 pm-10:21 am

1 stop16h 03m

Key West

Wed 5/6

11:46 am-7:16 pm

2 stops31h 30m

$286

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/2

6:18 pm-10:21 am

1 stop16h 03m

Key West

Wed 5/6

11:46 am-7:16 pm

2 stops31h 30m

$289

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

11:24 am-10:36 pm

2 stops11h 12m

Key West

Wed 5/13

4:20 pm-10:46 pm

1 stop6h 26m

$296

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 6/6

6:26 pm-10:24 am

1 stop15h 58m

Key West

Fri 6/12

12:07 pm-9:12 am

1 stop21h 05m

$299

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

5:30 am-3:07 pm

2 stops9h 37m

Key West

Wed 5/13

2:49 pm-11:59 pm

2 stops9h 10m

$301

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sun 5/17

6:00 am-1:49 pm

1 stop7h 49m

Key West

Tue 5/26

5:37 pm-11:51 pm

1 stop6h 14m

$302

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

6:00 am-11:29 am

1 stop5h 29m

Key West

Wed 5/13

11:24 am-11:26 pm

2 stops12h 02m

$309

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 6/6

5:01 pm-11:25 am

2 stops18h 24m

Key West

Fri 6/12

12:07 pm-9:12 am

1 stop21h 05m

$310
Quickest round-trip

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

6:00 am-11:29 am

1 stop5h 29m

Key West

Wed 5/13

4:20 pm-10:46 pm

1 stop6h 26m

$317

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

6:00 am-11:29 am

1 stop5h 29m

Key West

Wed 5/13

4:20 pm-10:46 pm

1 stop6h 26m

$341

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 typical price of a round-trip flight between Portland, Maine and Key West?

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 $356.

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 $434 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 10m

Direct flights

None
The fastest flight from Portland, Maine to Key West takes 6h 10m
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

Frequently asked questions about flying from Portland, Maine to Key West

  • 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 10m 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
9,529 reviews
Search United Airlines flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,368 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.1
11,544 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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