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Cheap flights from Key West to Portland from $147

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 9/11. 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.
Breeze Airways Logo
10:59 am - 10:28 am
EYW
-
PWM
23h 29m
1 stop
Breeze Airways Logo
5:30 pm - 9:24 am
PWM
-
EYW
15h 54m
2 stops
$342Breeze Airways
Fri, Sep 11 - Fri, Sep 18
Breeze Airways Logo
10:04 am - 5:51 pm
EYW
-
PWM
7h 47m
1 stop
Breeze Airways Logo
5:30 pm - 9:24 am
PWM
-
EYW
15h 54m
2 stops
$368Breeze Airways
Sat, Sep 12 - Fri, Sep 18
Delta Logo
2:35 pm - 10:33 pm
EYW
-
PWM
7h 58m
1 stop
Delta Logo
2:14 pm - 7:50 pm
PWM
-
EYW
5h 36m
1 stop
$389Delta
Fri, Sep 11 - Fri, Sep 18
American Airlines Logo
4:41 pm - 10:36 pm
EYW
-
PWM
5h 55m
1 stop
American Airlines Logo
8:00 am - 1:40 pm
PWM
-
EYW
5h 40m
1 stop
$391American Airlines
Wed, Jul 22 - Tue, Jul 28
American Airlines Logo
11:28 am - 10:36 pm
EYW
-
PWM
11h 08m
2 stops
American Airlines Logo
8:00 am - 1:40 pm
PWM
-
EYW
5h 40m
1 stop
$428American Airlines
Wed, Jul 22 - Tue, Jul 28
American Airlines Logo
10:15 am - 9:21 pm
EYW
-
PWM
11h 06m
2 stops
American Airlines Logo
6:00 am - 11:44 am
PWM
-
EYW
5h 44m
1 stop
$438American Airlines
Mon, Sep 7 - Tue, Sep 22
Delta Logo
11:45 am - 11:11 pm
EYW
-
PWM
11h 26m
2 stops
Delta Logo
6:02 am - 5:24 pm
PWM
-
EYW
11h 22m
2 stops
$440Delta
Fri, Sep 11 - Fri, Sep 18
American Airlines Logo
1:47 pm - 10:33 pm
EYW
-
PWM
8h 46m
2 stops
American Airlines Logo
7:16 am - 7:06 pm
PWM
-
EYW
11h 50m
2 stops
$465American Airlines
Wed, Jul 22 - Tue, Jul 28
Delta Logo
2:35 pm - 11:59 pm
EYW
-
PWM
9h 24m
2 stops
Delta Logo
6:02 am - 5:24 pm
PWM
-
EYW
11h 22m
2 stops
$469Delta
Sat, Sep 12 - Fri, Sep 18
American Airlines Logo
11:28 am - 9:46 pm
EYW
-
PWM
10h 18m
2 stops
American Airlines Logo
8:00 am - 1:40 pm
PWM
-
EYW
5h 40m
1 stop
$501American Airlines
Mon, Jun 29 - Fri, Jul 3

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United Airlines flights from Key West to Portland, Maine

Our best United Airlines deals on Key West to Portland, Maine flight tickets
United Airlines
Oct 27
EYW2:30 pmKey West
8h 27m
1 stop
PWM10:57 pmPortland
Oct 31
PWM6:00 amPortland
7h 02m
1 stop
EYW1:02 pmKey West
$617
United Airlines
Oct 27
EYW2:30 pmKey West
9h 29m
2 stops
PWM11:59 pmPortland
Oct 31
PWM6:00 amPortland
7h 02m
1 stop
EYW1:02 pmKey West
$622
United Airlines
Oct 27
EYW2:30 pmKey West
9h 29m
2 stops
PWM11:59 pmPortland
Oct 31
PWM5:06 pmPortland
23h 00m
2 stops
EYW4:06 pmKey West
$643

American Airlines flights from Key West to Portland, Maine

Our best American Airlines deals on Key West to Portland, Maine flight tickets
American Airlines
Jul 22
EYW4:41 pmKey West
5h 55m
1 stop
PWM10:36 pmPortland
Jul 28
PWM8:00 amPortland
5h 40m
1 stop
EYW1:40 pmKey West
$391
American Airlines
Jul 22
EYW11:28 amKey West
11h 08m
2 stops
PWM10:36 pmPortland
Jul 28
PWM8:00 amPortland
5h 40m
1 stop
EYW1:40 pmKey West
$428
American Airlines
Jul 22
EYW1:47 pmKey West
8h 46m
2 stops
PWM10:33 pmPortland
Jul 28
PWM7:16 amPortland
11h 50m
2 stops
EYW7:06 pmKey West
$465

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 June 17, 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

Fri 9/11

10:59 am-10:28 am

1 stop23h 29m

Portland

Fri 9/18

5:30 pm-9:24 am

2 stops15h 54m

$342

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 9/12

10:04 am-5:51 pm

1 stop7h 47m

Portland

Fri 9/18

5:30 pm-9:24 am

2 stops15h 54m

$368

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 9/11

2:35 pm-10:33 pm

1 stop7h 58m

Portland

Fri 9/18

2:14 pm-7:50 pm

1 stop5h 36m

$389
Quickest round-trip

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 7/22

4:41 pm-10:36 pm

1 stop5h 55m

Portland

Tue 7/28

8:00 am-1:40 pm

1 stop5h 40m

$391

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 7/22

11:28 am-10:36 pm

2 stops11h 08m

Portland

Tue 7/28

8:00 am-1:40 pm

1 stop5h 40m

$428

Key WestPortland

EYW - PWM

EYWPWM

Key West

Mon 9/7

10:15 am-9:21 pm

2 stops11h 06m

Portland

Tue 9/22

6:00 am-11:44 am

1 stop5h 44m

$438

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 9/11

11:45 am-11:11 pm

2 stops11h 26m

Portland

Fri 9/18

6:02 am-5:24 pm

2 stops11h 22m

$440

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 7/22

1:47 pm-10:33 pm

2 stops8h 46m

Portland

Tue 7/28

7:16 am-7:06 pm

2 stops11h 50m

$465

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 9/12

2:35 pm-11:59 pm

2 stops9h 24m

Portland

Fri 9/18

6:02 am-5:24 pm

2 stops11h 22m

$469

Key WestPortland

EYW - PWM

EYWPWM

Key West

Mon 6/29

11:28 am-9:46 pm

2 stops10h 18m

Portland

Fri 7/3

8:00 am-1:40 pm

1 stop5h 40m

$501

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 Portland 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

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

6h 12m

Direct flights

None
The fastest flight from Key West to Portland, Maine takes 6h 12m
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 6h 12m.

  • 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
11,670 reviews
Search American Airlines flights
DeltaPriceFrom $274Free CancellationRating
7.8
8,406 reviews
Search Delta 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
Conway
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
Oxford
Falmouth
Georgetown
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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