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$109+ Cheap flights from Florida Keys to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Florida Keys to Portland

Cheapest flights from Florida Keys to Portland
Explore the most affordable flight options available from Florida Keys to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:01 pmMIA - PWM
1 stop6h 42mDelta
Tue 1/202:35 pmPWM - MIA
1 stop8h 45mDelta
Deal found 12/15$217
This United Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:10 pmMIA - PWM
2 stops9h 49mUnited Airlines
Tue 1/206:00 amPWM - MIA
1 stop6h 38mUnited Airlines
Deal found 12/15$307
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:48 pmMIA - PWM
1 stop6h 34mUnited Airlines
Sun 1/46:00 amPWM - MIA
1 stop7h 21mUnited Airlines
Deal found 12/17$368
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:15 amMIA - PWM
1 stop6h 59mUnited Airlines
Sun 1/46:00 amPWM - MIA
1 stop6h 08mUnited Airlines
Deal found 12/17$413
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:48 pmMIA - PWM
1 stop6h 34mUnited Airlines
Sun 1/46:00 amPWM - MIA
1 stop7h 21mUnited Airlines
Deal found 12/16$419
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:10 pmMIA - PWM
2 stops9h 49mUnited Airlines
Sun 1/46:00 amPWM - MIA
1 stop6h 08mUnited Airlines
Deal found 12/17$440
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:34 amMIA - PWM
2 stops8h 05mAmerican Airlines
Sun 1/45:45 amPWM - MIA
1 stop7h 43mAmerican Airlines
Deal found 12/16$451
This Southwest deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:10 pmMIA - PWM
1 stop11h 55mSouthwest
Sun 1/45:30 pmPWM - MIA
1 stop5h 25mSouthwest
Deal found 12/16$468

Find flight deals from Florida Keys to Portland

Keep the following information in mind while searching for Florida Keys to Portland flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Delta)

One-way from

$109
(Delta)

Popular in

September

Cheapest in

November

Average price

$410
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
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From Florida Keys to Portland
Search Deals
One-way flight from Florida Keys to Portland
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys to Portland 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, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Florida Keys to Portland that are best for you.

Fly from

Florida Keys

Fly to

Portland

Route

Depart

Return

Price

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 1/13

5:35 pm-12:26 am

1 stop6h 51m

Portland

Tue 1/20

2:35 pm-11:20 pm

1 stop8h 45m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 1/13

4:22 pm-11:43 pm

1 stop7h 21m

Portland

Tue 1/20

3:58 pm-10:51 pm

1 stop6h 53m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 1/15

6:30 am-12:25 pm

1 stop5h 55m

Portland

Thu 1/22

12:45 pm-9:00 pm

1 stop8h 15m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 12/24

4:01 pm-10:43 pm

1 stop6h 42m

Portland

Tue 1/20

2:35 pm-11:20 pm

1 stop8h 45m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 2/5

5:10 pm-10:45 pm

1 stop5h 35m

Portland

Sun 2/8

12:45 pm-9:00 pm

1 stop8h 15m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 2/5

4:03 pm-10:07 pm

1 stop6h 04m

Portland

Sun 2/8

12:40 pm-9:10 pm

2 stops8h 30m

$222

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 1/15

6:40 am-12:05 pm

1 stop5h 25m

Portland

Thu 1/22

12:40 pm-9:10 pm

2 stops8h 30m

$222

MiamiPortland

MIA - PWM

MIAPWM

Miami

Fri 1/16

5:35 pm-12:20 am

1 stop6h 45m

Portland

Sun 1/18

12:48 pm-9:10 pm

1 stop8h 22m

$248

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 1/22

2:45 pm-10:27 pm

1 stop7h 42m

Portland

Sun 1/25

5:30 am-1:48 pm

1 stop8h 18m

$257

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 1/22

2:45 pm-10:27 pm

1 stop7h 42m

Portland

Mon 1/26

6:00 am-12:48 pm

1 stop6h 48m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 37 results
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Best time to book a flight from Florida Keys to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Florida Keys with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Portland

What is the cheapest month to book a flight from Florida Keys to Portland, Maine?

Currently, November is the cheapest month in which you can book a flight from Florida Keys to Portland, Maine (average of $170). Flying from Florida Keys to Portland, Maine in February is currently the most expensive (average of $331). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated December 18, 2025.
Read through reviews of airlines operating flights from Florida Keys to Portland, such as Southwest, Delta, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Overall

7.9

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Florida Keys?

    Portland (PWM) is the airport you will fly into if you book a flight from Florida Keys to Portland. It is only a 2.9 mi journey from Portland (PWM) to Portland’s city center.

  • How long is the flight from Florida Keys to Portland, Maine?

    There are many flights that can get you from Florida Keys to Portland, Maine in 5h 55m. Fly via Delta, American Airlines, or Southwest to get the fastest option. Airlines will cover a distance of 1354 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Florida Keys to Portland, Maine one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $108. American Airlines flights start at $118 while deals on United Airlines start at $129 one-way.

  • Can I find deals for flights from Florida Keys to Portland that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Portland.

  • Can I find deals for business class flights from Florida Keys to Portland?

    Yes. Cheapflights offers flight deals from Florida Keys to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Florida Keys to Portland, Maine?

    Currently, November is the cheapest month in which you can book a flight from Florida Keys to Portland, Maine (average of $170). Flying from Florida Keys to Portland, Maine in February is currently the most expensive (average of $331). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Alternative routes for Florida Keys to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Florida Keys to Portland

Discover the top 2 airlines that operate flights from Florida Keys to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$347FlexibilityNo cancel feeOn-time71%
DeltaCheapest$274Average$353FlexibilityNo cancel feeOn-timeN/A

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