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

United Airlines, American Airlines, and Delta 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 65% 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 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?

There are 2 operators available for flights from Key West Airport to Portland Airport as of November 2025.

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.

$165 Cheap Flights from Key West to Portland in 2025/26

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Find the cheapest flights from Key West to Portland

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:10 pm - 11:37 pmEYW-PWM

7h 27m2 stops

7:11 am - 1:41 pmPWM-EYW

6h 30m1 stop

$302American Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

10:06 am - 9:07 amEYW-PWM

23h 01m1 stop

5:06 pm - 11:20 amPWM-EYW

42h 14m2 stops

$305Multiple Airlines

Find Deal

Sun, Jan 11 - Fri, Jan 16

7:00 am - 4:28 pmEYW-PWM

9h 28m2 stops

5:34 am - 4:12 pmPWM-EYW

10h 38m2 stops

$307American Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

12:55 pm - 11:17 pmEYW-PWM

10h 22m2 stops

5:31 am - 12:02 pmPWM-EYW

6h 31m1 stop

$342American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

1:45 pm - 9:37 pmEYW-PWM

7h 52m1 stop

7:11 am - 4:12 pmPWM-EYW

9h 01m1 stop

$343American Airlines

Find Deal

Tue, Dec 9 - Sat, Dec 13

12:55 pm - 11:17 pmEYW-PWM

10h 22m2 stops

12:43 pm - 10:23 pmPWM-EYW

9h 40m2 stops

$347American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

11:47 am - 10:50 pmEYW-PWM

11h 03m2 stops

7:00 am - 1:45 pmPWM-EYW

6h 45m1 stop

$408American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

1:46 pm - 10:50 pmEYW-PWM

9h 04m2 stops

12:43 pm - 10:49 pmPWM-EYW

10h 06m2 stops

$413American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

11:47 am - 10:49 pmEYW-PWM

11h 02m2 stops

7:00 am - 1:45 pmPWM-EYW

6h 45m1 stop

$421American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

5:10 pm - 11:17 pmEYW-PWM

6h 07m1 stop

7:00 am - 1:45 pmPWM-EYW

6h 45m1 stop

$467American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

American Airlines flights from Key West to Portland, Maine

Our best American Airlines deals on Key West to Portland, Maine flight tickets

American Airlines

Dec 9

EYW4:10 pmKey West

7h 27m

2 stops

PWM11:37 pmPortland

Dec 13

PWM7:11 amPortland

6h 30m

1 stop

EYW1:41 pmKey West

$302

Find similar

American Airlines

Dec 9

EYW7:00 amKey West

9h 28m

2 stops

PWM4:28 pmPortland

Dec 13

PWM5:34 amPortland

10h 38m

2 stops

EYW4:12 pmKey West

$307

Find similar

American Airlines

Feb 14

EYW12:55 pmKey West

10h 22m

2 stops

PWM11:17 pmPortland

Feb 18

PWM5:31 amPortland

6h 31m

1 stop

EYW12:02 pmKey West

$342

Find similar

momondo Fare Finder

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

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 12/9

4:10 pm-11:37 pm

2 stops7h 27m

Portland

Sat 12/13

7:11 am-1:41 pm

1 stop6h 30m

$302

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sun 1/11

10:06 am-9:07 am

1 stop23h 01m

Portland

Fri 1/16

5:06 pm-11:20 am

2 stops42h 14m

$305

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 12/9

7:00 am-4:28 pm

2 stops9h 28m

Portland

Sat 12/13

5:34 am-4:12 pm

2 stops10h 38m

$307

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

12:55 pm-11:17 pm

2 stops10h 22m

Portland

Wed 2/18

5:31 am-12:02 pm

1 stop6h 31m

$342

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 12/9

1:45 pm-9:37 pm

1 stop7h 52m

Portland

Sat 12/13

7:11 am-4:12 pm

1 stop9h 01m

$343

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

12:55 pm-11:17 pm

2 stops10h 22m

Portland

Wed 2/18

12:43 pm-10:23 pm

2 stops9h 40m

$347

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

11:47 am-10:50 pm

2 stops11h 03m

Portland

Wed 2/18

7:00 am-1:45 pm

1 stop6h 45m

$408

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

1:46 pm-10:50 pm

2 stops9h 04m

Portland

Wed 2/18

12:43 pm-10:49 pm

2 stops10h 06m

$413

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

11:47 am-10:49 pm

2 stops11h 02m

Portland

Wed 2/18

7:00 am-1:45 pm

1 stop6h 45m

$421

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

5:10 pm-11:17 pm

1 stop6h 07m

Portland

Wed 2/18

7:00 am-1:45 pm

1 stop6h 45m

$467

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest day to depart on your flight to Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Key West is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $312. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Key West because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $489.

What is the cheapest time of day to depart on your flight to Portland, Maine?

In the afternoon is the cheapest time of day to fly from Key West to Portland, Maine when you can find flight prices for as low as $392. Flying to Portland, Maine in the afternoon is an ideal time because this is during off-peak travel hours. Try not to purchase tickets at noon because they tend to be around $482. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 58m
Direct flights	None

The fastest flight from Key West to Portland, Maine takes 5h 58m

There are no direct flights from Key West to Portland, Maine. There are no popular flight routes from Key West to Portland, Maine.

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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 19m.
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?
There are 2 operators available for flights from Key West Airport to Portland Airport as of November 2025.
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?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Key West to Portland, Maine is American Airlines (68% of total bookings). The next most popular airline is Delta (32%).

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 Airlines	PriceFrom $268	Free Cancellation	Rating 7.2 11,038 reviews		Search American Airlines flights
Delta	PriceFrom $274	Free Cancellation	Rating 7.9 7,998 reviews		Search Delta flights

North Conway

Boothbay Harbor

Jackson

Conway

Lewiston

Freeport

Brunswick

Bartlett

Auburn

Gorham

Windham

Intervale

Oxford

Bath

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.