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

American Airlines, Delta, and Breeze Airways 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 62% 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 is 1 operator available for flights from Key West Airport to Portland Airport as of July 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

Q: What is the typical price of a round-trip flight between Key West and Portland, Maine?

Prices are currently low for flights on this route. Typical prices usually range from $316 to $443. The lowest price recently found on this route was $269.

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Find the cheapest flights from Key West to Portland

Round-trip

One-way

Cheap round-trip flights

6:10 pm - 12:11 amEYW-PWM

6h 01m1 stop

1:35 pm - 8:07 pmPWM-EYW

6h 32m1 stop

$269Delta

Find Deal

mié., sep. 17 - mié., sep. 24

6:20 pm - 12:03 amEYW-PWM

5h 43m1 stop

6:00 am - 5:15 pmPWM-EYW

11h 15m2 stops

$274Delta

Find Deal

mié., sep. 10 - mié., sep. 17

11:52 am - 12:53 amEYW-PWM

13h 01m2 stops

6:00 am - 5:15 pmPWM-EYW

11h 15m2 stops

$279Delta

Find Deal

mié., sep. 10 - mié., sep. 17

11:25 am - 11:45 pmEYW-PWM

12h 20m2 stops

6:00 am - 1:29 pmPWM-EYW

7h 29m2 stops

$286American Airlines

Find Deal

mié., sep. 17 - mié., sep. 24

5:02 pm - 10:59 pmEYW-PWM

5h 57m1 stop

6:00 am - 1:51 pmPWM-EYW

7h 51m1 stop

$309American Airlines

Find Deal

mié., ago. 27 - mar., sep. 2

2:22 pm - 11:59 pmEYW-PWM

9h 37m2 stops

6:00 am - 2:25 pmPWM-EYW

8h 25m1 stop

$329United Airlines

Find Deal

mar., ago. 12 - mar., ago. 19

2:12 pm - 11:59 pmEYW-PWM

9h 47m2 stops

6:00 am - 12:41 pmPWM-EYW

6h 41m1 stop

$334United Airlines

Find Deal

mié., ago. 13 - dom., ago. 17

9:47 am - 1:51 pmEYW-PWM

52h 04m3 stops

2:21 pm - 11:52 amPWM-EYW

45h 31m2 stops

$872Breeze Airways

Find Deal

mié., sep. 10 - mié., sep. 17

9:47 am - 1:51 pmEYW-PWM

52h 04m3 stops

2:21 pm - 11:52 amPWM-EYW

45h 31m2 stops

$885Breeze Airways

Find Deal

mié., sep. 17 - mié., sep. 24

10:02 am - 8:12 pmEYW-PWM

34h 10m3 stops

8:52 pm - 4:41 pmPWM-EYW

19h 49m2 stops

$1,064

Find Deal

mié., ago. 13 - dom., ago. 17

United Airlines flights from Key West to Portland, Maine

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

United Airlines

Aug 12

EYW2:22 pmKey West

9h 37m

2 stops

PWM11:59 pmPortland

Aug 19

PWM6:00 amPortland

8h 25m

1 stop

EYW2:25 pmKey West

$329

Find similar

United Airlines

Aug 13

EYW2:12 pmKey West

9h 47m

2 stops

PWM11:59 pmPortland

Aug 17

PWM6:00 amPortland

6h 41m

1 stop

EYW12:41 pmKey West

$334

Find similar

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 10

EYW9:47 amKey West

52h 04m

3 stops

PWM1:51 pmPortland

Sep 17

PWM2:21 pmPortland

45h 31m

2 stops

EYW11:52 amKey West

$872

Find similar

Breeze Airways

Sep 17

EYW9:47 amKey West

52h 04m

3 stops

PWM1:51 pmPortland

Sep 24

PWM2:21 pmPortland

45h 31m

2 stops

EYW11:52 amKey West

$885

Find similar

Breeze Airways

Sep 10

EYW9:47 amKey West

52h 04m

3 stops

PWM1:51 pmPortland

Sep 17

PWM4:41 pmPortland

17h 38m

3 stops

EYW10:19 amKey West

$970

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/17

6:10 pm-12:11 am

1 stop6h 01m

Portland

mié. 9/24

1:35 pm-8:07 pm

1 stop6h 32m

$269

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/10

6:20 pm-12:03 am

1 stop5h 43m

Portland

mié. 9/17

6:00 am-5:15 pm

2 stops11h 15m

$274

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/10

11:52 am-12:53 am

2 stops13h 01m

Portland

mié. 9/17

6:00 am-5:15 pm

2 stops11h 15m

$279

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/17

11:25 am-11:45 pm

2 stops12h 20m

Portland

mié. 9/24

6:00 am-1:29 pm

2 stops7h 29m

$286

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 8/27

5:02 pm-10:59 pm

1 stop5h 57m

Portland

mar. 9/2

6:00 am-1:51 pm

1 stop7h 51m

$309

Key WestPortland

EYW - PWM

EYWPWM

Key West

mar. 8/12

2:22 pm-11:59 pm

2 stops9h 37m

Portland

mar. 8/19

6:00 am-2:25 pm

1 stop8h 25m

$329

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 8/13

2:12 pm-11:59 pm

2 stops9h 47m

Portland

dom. 8/17

6:00 am-12:41 pm

1 stop6h 41m

$334

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/10

9:47 am-1:51 pm

3 stops52h 04m

Portland

mié. 9/17

2:21 pm-11:52 am

2 stops45h 31m

$872

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/17

9:47 am-1:51 pm

3 stops52h 04m

Portland

mié. 9/24

2:21 pm-11:52 am

2 stops45h 31m

$885

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 8/13

10:02 am-8:12 pm

3 stops34h 10m

Portland

dom. 8/17

8:52 pm-4:41 pm

2 stops19h 49m

$1,064

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 typical price of a round-trip flight between Key West and Portland, Maine?

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

Best Price Found	$165
Fastest flight time	5h 43m
Direct flights	None
Airports in Portland, Maine	1 airport

The best one-way flight to Portland, Maine from Key West in the past 72 hours is $165. The best round-trip flight deal from Key West to Portland, Maine found on momondo in the last 72 hours is $269.

The fastest flight from Key West to Portland, Maine takes 5h 43m

There are no direct flights from Key West to Portland, Maine. Popular non-direct route for this connection is Key West Airport - Portland Airport.

There is 1 airport near Portland, Maine: Portland (PWM)

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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 43m.
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 is 1 operator available for flights from Key West Airport to Portland Airport as of July 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 (100% of total bookings).

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 $258	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

North Conway

Boothbay Harbor

Jackson

Conway

Freeport

Bartlett

Lewiston

Gorham

Brunswick

Auburn

Intervale

Windham

Falmouth

Bath

Georgetown

Oxford

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.