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Cheap flights from Key West to Portland from $149

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 Portland departing on 9/30. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Key West to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:34 pm - 11:41 pm
EYW
-
PWM
6h 07m
1 stop
American Airlines Logo
7:03 am - 2:36 pm
PWM
-
EYW
7h 33m
1 stop
$301American Airlines
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
5:34 pm - 11:41 pm
EYW
-
PWM
6h 07m
1 stop
American Airlines Logo
7:00 am - 1:54 pm
PWM
-
EYW
6h 54m
1 stop
$301American Airlines
Wed, Oct 21 - Tue, Oct 27
Delta Logo
7:40 am - 1:02 pm
EYW
-
PWM
5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Wed, Oct 21 - Tue, Oct 27
Delta Logo
6:10 pm - 11:35 pm
EYW
-
PWM
5h 25m
1 stop
Delta Logo
11:25 am - 8:01 pm
PWM
-
EYW
8h 36m
2 stops
$306Delta
Wed, Oct 21 - Tue, Oct 27
Delta Logo
7:40 am - 4:02 pm
EYW
-
PWM
8h 22m
2 stops
Delta Logo
11:25 am - 8:01 pm
PWM
-
EYW
8h 36m
2 stops
$311Delta
Wed, Oct 21 - Tue, Oct 27
Multiple Airlines Logo
11:57 am - 10:38 pm
EYW
-
PWM
10h 41m
1 stop
Multiple Airlines Logo
8:00 am - 11:06 am
PWM
-
EYW
27h 06m
2 stops
$315Multiple Airlines
Fri, Aug 14 - Tue, Aug 18
Delta Logo
6:10 pm - 11:35 pm
EYW
-
PWM
5h 25m
1 stop
Delta Logo
11:25 am - 8:01 pm
PWM
-
EYW
8h 36m
2 stops
$326Delta
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
2:15 pm - 9:51 pm
EYW
-
PWM
7h 36m
1 stop
American Airlines Logo
6:00 am - 12:27 pm
PWM
-
EYW
6h 27m
1 stop
$336American Airlines
Tue, Oct 20 - Fri, Oct 30
American Airlines Logo
2:15 pm - 9:51 pm
EYW
-
PWM
7h 36m
1 stop
American Airlines Logo
12:06 pm - 6:49 pm
PWM
-
EYW
6h 43m
1 stop
$336American Airlines
Tue, Oct 20 - Fri, Oct 30
American Airlines Logo
1:50 pm - 10:00 pm
EYW
-
PWM
8h 10m
1 stop
American Airlines Logo
5:30 am - 1:45 pm
PWM
-
EYW
8h 15m
1 stop
$401American Airlines
Wed, Aug 19 - Tue, Aug 25

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Delta flights from Key West to Portland, Maine

Our best Delta deals on Key West to Portland, Maine flight tickets
Delta
Oct 21
EYW7:40 amKey West
5h 22m
1 stop
PWM1:02 pmPortland
Oct 27
PWM2:09 pmPortland
5h 52m
1 stop
EYW8:01 pmKey West
$301
Delta
Oct 21
EYW6:10 pmKey West
5h 25m
1 stop
PWM11:35 pmPortland
Oct 27
PWM11:25 amPortland
8h 36m
2 stops
EYW8:01 pmKey West
$306
Delta
Oct 21
EYW7:40 amKey West
8h 22m
2 stops
PWM4:02 pmPortland
Oct 27
PWM11:25 amPortland
8h 36m
2 stops
EYW8:01 pmKey West
$311

United Airlines flights from Key West to Portland, Maine

Our best United Airlines deals on Key West to Portland, Maine flight tickets
United Airlines
Nov 11
EYW2:50 pmKey West
8h 31m
1 stop
PWM11:21 pmPortland
Nov 14
PWM6:00 amPortland
7h 52m
1 stop
EYW1:52 pmKey West
$587
United Airlines
Nov 11
EYW2:50 pmKey West
8h 31m
1 stop
PWM11:21 pmPortland
Nov 14
PWM8:45 amPortland
30h 44m
2 stops
EYW3:29 pmKey West
$641
United Airlines
Nov 11
EYW2:50 pmKey West
8h 31m
1 stop
PWM11:21 pmPortland
Nov 14
PWM3:10 pmPortland
24h 19m
3 stops
EYW3:29 pmKey West
$695

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 August 3, 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

Cheapest round-trip

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 10/21

5:34 pm-11:41 pm

1 stop6h 07m

Portland

Tue 10/27

7:03 am-2:36 pm

1 stop7h 33m

$301

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 10/21

5:34 pm-11:41 pm

1 stop6h 07m

Portland

Tue 10/27

7:00 am-1:54 pm

1 stop6h 54m

$301
Quickest round-trip

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 10/21

7:40 am-1:02 pm

1 stop5h 22m

Portland

Tue 10/27

2:09 pm-8:01 pm

1 stop5h 52m

$301

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 10/21

6:10 pm-11:35 pm

1 stop5h 25m

Portland

Tue 10/27

11:25 am-8:01 pm

2 stops8h 36m

$306

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 10/21

7:40 am-4:02 pm

2 stops8h 22m

Portland

Tue 10/27

11:25 am-8:01 pm

2 stops8h 36m

$311

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 8/14

11:57 am-10:38 pm

1 stop10h 41m

Portland

Tue 8/18

8:00 am-11:06 am

2 stops27h 06m

$315

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 10/21

6:10 pm-11:35 pm

1 stop5h 25m

Portland

Tue 10/27

11:25 am-8:01 pm

2 stops8h 36m

$326

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 10/20

2:15 pm-9:51 pm

1 stop7h 36m

Portland

Fri 10/30

6:00 am-12:27 pm

1 stop6h 27m

$336

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 10/20

2:15 pm-9:51 pm

1 stop7h 36m

Portland

Fri 10/30

12:06 pm-6:49 pm

1 stop6h 43m

$336

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 8/19

1:50 pm-10:00 pm

1 stop8h 10m

Portland

Tue 8/25

5:30 am-1:45 pm

1 stop8h 15m

$401

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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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

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

You could potentially save up to 7% on your flight if you consider stops on a Key West to Portland, Maine flight.

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

5h 25m

Direct flights

None
The fastest flight from Key West to Portland, Maine takes 5h 25m
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

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

  • 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 5h 25m.

  • 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 $276Free CancellationRating
7.1
11,844 reviews
Search American Airlines flights

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Lewiston
Brunswick
Freeport
Bartlett
Gorham
Conway
Auburn
Windham
Bath
Intervale
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.

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