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Cheap flights from Portland, Maine to Key West from $143

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 5/23. 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.
Delta Logo
1:55 pm - 7:53 pm
PWM
-
EYW
5h 58m
1 stop
Delta Logo
2:28 pm - 11:05 pm
EYW
-
PWM
8h 37m
1 stop
$309Delta
Wed, Jun 10 - Tue, Jun 16
Delta Logo
6:00 am - 5:27 pm
PWM
-
EYW
11h 27m
2 stops
Delta Logo
2:28 pm - 11:05 pm
EYW
-
PWM
8h 37m
1 stop
$314Delta
Wed, Jun 10 - Tue, Jun 16
Delta Logo
6:00 am - 1:43 pm
PWM
-
EYW
7h 43m
1 stop
Delta Logo
2:24 pm - 12:59 am
EYW
-
PWM
10h 35m
2 stops
$315Delta
Tue, Jun 30 - Thu, Jul 9
Delta Logo
6:00 am - 12:23 pm
PWM
-
EYW
6h 23m
1 stop
Delta Logo
11:45 am - 12:59 am
EYW
-
PWM
13h 14m
2 stops
$329Delta
Tue, Jun 30 - Sat, Jul 11
Delta Logo
6:00 am - 12:23 pm
PWM
-
EYW
6h 23m
1 stop
Delta Logo
11:45 am - 12:59 am
EYW
-
PWM
13h 14m
2 stops
$331Delta
Tue, Jun 30 - Sat, Jul 11
Delta Logo
1:55 pm - 7:53 pm
PWM
-
EYW
5h 58m
1 stop
Delta Logo
2:24 pm - 12:59 am
EYW
-
PWM
10h 35m
2 stops
$332Delta
Thu, Jul 2 - Wed, Jul 8
Delta Logo
6:25 am - 5:27 pm
PWM
-
EYW
11h 02m
2 stops
Delta Logo
2:28 pm - 12:52 am
EYW
-
PWM
10h 24m
2 stops
$334Delta
Wed, Jun 10 - Tue, Jun 16
Multiple Airlines Logo
3:11 pm - 6:28 pm
PWM
-
EYW
27h 17m
1 stop
Multiple Airlines Logo
8:48 pm - 9:12 am
EYW
-
PWM
12h 24m
1 stop
$343Multiple Airlines
Thu, Jul 16 - Sun, Jul 19
Delta Logo
1:55 pm - 7:53 pm
PWM
-
EYW
5h 58m
1 stop
Delta Logo
11:45 am - 12:59 am
EYW
-
PWM
13h 14m
2 stops
$347Delta
Thu, Jul 2 - Sat, Jul 11
Delta Logo
6:00 am - 1:43 pm
PWM
-
EYW
7h 43m
1 stop
Delta Logo
11:45 am - 12:59 am
EYW
-
PWM
13h 14m
2 stops
$348Delta
Sun, Jul 5 - Sat, Jul 11

Delta flights from Portland, Maine to Key West

Our best Delta deals on Portland, Maine to Key West flight tickets
Delta
Jun 10
PWM1:55 pmPortland
5h 58m
1 stop
EYW7:53 pmKey West
Jun 16
EYW2:28 pmKey West
8h 37m
1 stop
PWM11:05 pmPortland
$309
Delta
Jun 10
PWM6:00 amPortland
11h 27m
2 stops
EYW5:27 pmKey West
Jun 16
EYW2:28 pmKey West
8h 37m
1 stop
PWM11:05 pmPortland
$314
Delta
Jun 30
PWM6:00 amPortland
7h 43m
1 stop
EYW1:43 pmKey West
Jul 9
EYW2:24 pmKey West
10h 35m
2 stops
PWM12:59 amPortland
$315

Breeze Airways flights from Portland, Maine to Key West

Our best Breeze Airways deals on Portland, Maine to Key West flight tickets
Breeze Airways
Jun 13
PWM6:26 pmPortland
15h 58m
1 stop
EYW10:24 amKey West
Jun 19
EYW12:07 pmKey West
21h 05m
1 stop
PWM9:12 amPortland
$369
Breeze Airways
Jun 16
PWM4:44 pmPortland
18h 22m
2 stops
EYW11:06 amKey West
Jun 19
EYW12:07 pmKey West
21h 05m
1 stop
PWM9:12 amPortland
$377
Breeze Airways
Jul 4
PWM6:38 pmPortland
24h 35m
1 stop
EYW7:13 pmKey West
Jul 10
EYW12:07 pmKey West
21h 05m
1 stop
PWM9:12 amPortland
$380

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 May 15, 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
Quickest round-trip

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 6/10

1:55 pm-7:53 pm

1 stop5h 58m

Key West

Tue 6/16

2:28 pm-11:05 pm

1 stop8h 37m

$309

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 6/10

6:00 am-5:27 pm

2 stops11h 27m

Key West

Tue 6/16

2:28 pm-11:05 pm

1 stop8h 37m

$314

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 6/30

6:00 am-1:43 pm

1 stop7h 43m

Key West

Thu 7/9

2:24 pm-12:59 am

2 stops10h 35m

$315

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 6/30

6:00 am-12:23 pm

1 stop6h 23m

Key West

Sat 7/11

11:45 am-12:59 am

2 stops13h 14m

$329

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 6/30

6:00 am-12:23 pm

1 stop6h 23m

Key West

Sat 7/11

11:45 am-12:59 am

2 stops13h 14m

$331

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/2

1:55 pm-7:53 pm

1 stop5h 58m

Key West

Wed 7/8

2:24 pm-12:59 am

2 stops10h 35m

$332

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 6/10

6:25 am-5:27 pm

2 stops11h 02m

Key West

Tue 6/16

2:28 pm-12:52 am

2 stops10h 24m

$334

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/16

3:11 pm-6:28 pm

1 stop27h 17m

Key West

Sun 7/19

8:48 pm-9:12 am

1 stop12h 24m

$343

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/2

1:55 pm-7:53 pm

1 stop5h 58m

Key West

Sat 7/11

11:45 am-12:59 am

2 stops13h 14m

$347

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sun 7/5

6:00 am-1:43 pm

1 stop7h 43m

Key West

Sat 7/11

11:45 am-12:59 am

2 stops13h 14m

$348

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, August 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 $294. If you are unable to visit Key West during the month of August, then departing from Portland, Maine during the month May is also very affordable. Most momondo users find prices during this month for around $372.

How far in advance should I book a flight from Portland, Maine 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 $448 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.

Can stopping save me money on Portland, Maine to Key West flights?

You could potentially save up to 19% on your flight if you consider stops on a Portland, Maine to Key West flight.

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

7h 30m

Direct flights

None
The fastest flight from Portland, Maine to Key West takes 7h 30m
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 7h 30m 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
9,717 reviews
Search United Airlines flights
DeltaPriceFrom $256Free CancellationRating
7.9
8,452 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.1
11,662 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.
Start using Trips
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