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Cheap flights from Key West to Portland from $208

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 6/3. 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 Key West to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Breeze Airways Logo
12:59 pm - 5:51 pm
EYW
-
PWM
28h 52m
1 stop
Breeze Airways Logo
6:31 pm - 11:21 am
PWM
-
EYW
16h 50m
1 stop
$287Breeze Airways
Fri, Sep 18 - Sat, Sep 26
Breeze Airways Logo
10:04 am - 5:51 pm
EYW
-
PWM
7h 47m
1 stop
Breeze Airways Logo
6:31 pm - 11:21 am
PWM
-
EYW
16h 50m
1 stop
$293Breeze Airways
Wed, Sep 16 - Sat, Sep 26
Breeze Airways Logo
12:59 pm - 5:51 pm
EYW
-
PWM
28h 52m
1 stop
Breeze Airways Logo
5:30 pm - 9:24 am
PWM
-
EYW
15h 54m
2 stops
$297Breeze Airways
Fri, Sep 18 - Fri, Sep 25
Delta Logo
11:45 am - 11:59 pm
EYW
-
PWM
12h 14m
2 stops
Delta Logo
6:30 am - 5:14 pm
PWM
-
EYW
10h 44m
2 stops
$301Delta
Wed, Sep 16 - Tue, Sep 22
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
$302Breeze Airways
Wed, Sep 16 - Fri, Sep 25
Breeze Airways Logo
12:59 pm - 5:51 pm
EYW
-
PWM
28h 52m
1 stop
Breeze Airways Logo
9:48 am - 10:19 am
PWM
-
EYW
24h 31m
1 stop
$304Breeze Airways
Fri, Sep 18 - Wed, Sep 23
Breeze Airways Logo
10:04 am - 5:51 pm
EYW
-
PWM
7h 47m
1 stop
Breeze Airways Logo
9:48 am - 10:19 am
PWM
-
EYW
24h 31m
1 stop
$309Breeze Airways
Wed, Sep 16 - Wed, Sep 23
Breeze Airways Logo
10:59 am - 9:08 am
EYW
-
PWM
22h 09m
1 stop
Breeze Airways Logo
6:31 pm - 11:21 am
PWM
-
EYW
16h 50m
1 stop
$310Breeze Airways
Thu, Sep 17 - Sat, Sep 26
Delta Logo
11:45 am - 11:59 pm
EYW
-
PWM
12h 14m
2 stops
Delta Logo
6:30 am - 5:14 pm
PWM
-
EYW
10h 44m
2 stops
$314Delta
Thu, Sep 17 - Tue, Sep 22
Breeze Airways Logo
10:04 am - 5:51 pm
EYW
-
PWM
7h 47m
1 stop
Breeze Airways Logo
7:35 am - 9:24 am
PWM
-
EYW
25h 49m
2 stops
$315Breeze Airways
Wed, Sep 16 - Tue, Sep 22

American Airlines flights from Key West to Portland, Maine

Our best American Airlines deals on Key West to Portland, Maine flight tickets
American Airlines
Sep 16
EYW12:05 pmKey West
11h 19m
2 stops
PWM11:24 pmPortland
Sep 23
PWM8:01 amPortland
10h 26m
2 stops
EYW6:27 pmKey West
$351
American Airlines
May 21
EYW5:37 pmKey West
6h 14m
1 stop
PWM11:51 pmPortland
May 25
PWM6:00 amPortland
7h 41m
1 stop
EYW1:41 pmKey West
$392
American Airlines
May 21
EYW5:37 pmKey West
6h 14m
1 stop
PWM11:51 pmPortland
May 25
PWM6:00 amPortland
7h 07m
2 stops
EYW1:07 pmKey West
$409

Breeze Airways flights from Key West to Portland, Maine

Our best Breeze Airways deals on Key West to Portland, Maine flight tickets
Breeze Airways
Sep 18
EYW12:59 pmKey West
28h 52m
1 stop
PWM5:51 pmPortland
Sep 26
PWM6:31 pmPortland
16h 50m
1 stop
EYW11:21 amKey West
$287
Breeze Airways
Sep 16
EYW10:04 amKey West
7h 47m
1 stop
PWM5:51 pmPortland
Sep 26
PWM6:31 pmPortland
16h 50m
1 stop
EYW11:21 amKey West
$293
Breeze Airways
Sep 18
EYW12:59 pmKey West
28h 52m
1 stop
PWM5:51 pmPortland
Sep 25
PWM5:30 pmPortland
15h 54m
2 stops
EYW9:24 amKey West
$297

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 April 18, 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 9/18

12:59 pm-5:51 pm

1 stop28h 52m

Portland

Sat 9/26

6:31 pm-11:21 am

1 stop16h 50m

$287

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/16

10:04 am-5:51 pm

1 stop7h 47m

Portland

Sat 9/26

6:31 pm-11:21 am

1 stop16h 50m

$293

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 9/18

12:59 pm-5:51 pm

1 stop28h 52m

Portland

Fri 9/25

5:30 pm-9:24 am

2 stops15h 54m

$297
Quickest round-trip

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/16

11:45 am-11:59 pm

2 stops12h 14m

Portland

Tue 9/22

6:30 am-5:14 pm

2 stops10h 44m

$301

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/16

10:04 am-5:51 pm

1 stop7h 47m

Portland

Fri 9/25

5:30 pm-9:24 am

2 stops15h 54m

$302

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 9/18

12:59 pm-5:51 pm

1 stop28h 52m

Portland

Wed 9/23

9:48 am-10:19 am

1 stop24h 31m

$304

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/16

10:04 am-5:51 pm

1 stop7h 47m

Portland

Wed 9/23

9:48 am-10:19 am

1 stop24h 31m

$309

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 9/17

10:59 am-9:08 am

1 stop22h 09m

Portland

Sat 9/26

6:31 pm-11:21 am

1 stop16h 50m

$310

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 9/17

11:45 am-11:59 pm

2 stops12h 14m

Portland

Tue 9/22

6:30 am-5:14 pm

2 stops10h 44m

$314

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/16

10:04 am-5:51 pm

1 stop7h 47m

Portland

Tue 9/22

7:35 am-9:24 am

2 stops25h 49m

$315

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

What is the cheapest airline that flies from Key West to Portland?

Breeze Airways, American Airlines, and United Airlines are the most popular carriers operating from Key West to Portland

What airlines fly to Portland, Maine?

American Airlines, JetBlue and Delta are the top three most popular airlines that fly to Portland, Maine from Key West according to our data. American Airlines is the first choice among our users, with 73% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 3 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

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

9h 18m

Direct flights

None
The fastest flight from Key West to Portland, Maine takes 9h 18m
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 9h 18m.

  • 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
11,604 reviews
Search American Airlines flights
DeltaPriceFrom $274Free CancellationRating
7.9
8,424 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
Conway
Freeport
Lewiston
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
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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