Florida Keys

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

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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Jan 16 — Jan 231
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Cheap flight deals from Portland to Florida Keys

Cheapest flights from Portland to Florida Keys
Explore the most affordable flight options available from Portland to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 17, 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 12/315:45 amPWM - MIA
1 stop8h 08mDelta
Mon 1/125:35 pmMIA - PWM
1 stop6h 45mDelta
Deal found 12/15$308
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 12/315:45 amPWM - MIA
1 stop8h 08mDelta
Tue 1/1311:21 amMIA - PWM
2 stops12h 01mDelta
Deal found 12/15$359
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.
Tue 12/3010:19 amPWM - MIA
2 stops11h 51mUnited Airlines
Mon 1/127:15 amMIA - PWM
1 stop6h 41mUnited Airlines
Deal found 12/16$370
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:17 amPWM - MIA
1 stop5h 53mAmerican Airlines
Thu 1/84:03 pmMIA - PWM
1 stop6h 04mAmerican Airlines
Deal found 12/15$373
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amPWM - MIA
1 stop5h 35mAmerican Airlines
Wed 12/2411:44 amMIA - PWM
1 stop4h 55mAmerican Airlines
Deal found 12/17$397
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:45 amPWM - MIA
1 stop7h 11mDelta
Mon 12/294:01 pmMIA - PWM
1 stop6h 42mDelta
Deal found 12/17$401
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.
Sat 12/205:39 amPWM - MIA
1 stop5h 39mAmerican Airlines
Thu 12/259:59 amMIA - PWM
1 stop6h 44mAmerican Airlines
Deal found 12/16$410
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:16 amPWM - EYW
1 stop20h 59mBreeze Airways
Sun 1/48:55 amEYW - PWM
1 stop24h 11mBreeze Airways
Deal found 12/15$413
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:08 amPWM - MIA
1 stop8h 37mDelta
Wed 12/244:01 pmMIA - PWM
1 stop6h 42mDelta
Deal found 12/17$416
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:17 amPWM - EYW
1 stop8h 40mAmerican Airlines
Sun 12/215:39 pmEYW - PWM
1 stop6h 03mAmerican Airlines
Deal found 12/17$427
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 12/305:30 amPWM - MIA
1 stop12h 30mSouthwest
Mon 1/127:15 amMIA - PWM
1 stop7h 40mSouthwest
Deal found 12/16$440
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:00 amPWM - EYW
2 stops9h 57mAmerican Airlines
Tue 12/305:10 pmEYW - PWM
1 stop5h 45mAmerican Airlines
Deal found 12/17$445

Find flight deals from Portland to Florida Keys

Keep the following information in mind while searching for Portland to Florida Keys flight deals. Data was last updated December 17, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$217
(Southwest)

One-way from

$109
(Delta)

Popular in

December

Cheapest in

September

Average price

$327
Provider with most accurate pricing for Boston Logan Intl-Miami flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Miami flights.
From Portland to Florida Keys
One-way flight from Portland to Florida Keys
Highest demand for flights based on searches. 12% potential increase in price ($33 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in December 2025

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Florida Keys 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 17, 2025.
Use the filters below to find and compare flights from Portland to Florida Keys that are best for you.

Fly from

Portland

Fly to

Florida Keys

Route

Depart

Return

Price

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sun 2/1

3:55 pm-10:25 pm

1 stop6h 30m

Miami

Sat 2/7

7:00 am-2:45 pm

1 stop7h 45m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 1/30

2:35 pm-11:20 pm

1 stop8h 45m

Miami

Fri 2/6

4:32 pm-10:27 pm

1 stop5h 55m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sun 2/1

5:20 am-12:52 pm

1 stop7h 32m

Miami

Thu 2/12

6:36 am-12:13 pm

1 stop5h 37m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 1/14

3:30 pm-9:00 pm

1 stop5h 30m

Miami

Wed 1/21

7:15 am-12:10 pm

1 stop4h 55m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 1/23

2:35 pm-11:20 pm

1 stop8h 45m

Miami

Sat 1/24

7:40 am-1:45 pm

1 stop6h 05m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Thu 2/5

3:55 pm-10:25 pm

1 stop6h 30m

Miami

Mon 2/9

6:30 am-12:25 pm

1 stop5h 55m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Mon 1/26

2:35 pm-11:20 pm

1 stop8h 45m

Miami

Sat 1/31

7:00 am-12:30 pm

1 stop5h 30m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Thu 3/5

6:00 am-5:28 pm

2 stops11h 28m

Miami

Tue 3/10

4:49 pm-10:51 pm

1 stop6h 02m

$222

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 3/4

6:00 am-1:37 pm

1 stop7h 37m

Miami

Tue 3/10

12:11 pm-10:51 pm

2 stops10h 40m

$222

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 1/13

6:00 am-12:54 pm

1 stop6h 54m

Miami

Tue 1/20

9:24 am-5:16 pm

1 stop7h 52m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 40 results
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Best time to book a flight from Portland to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Portland 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 Portland to Florida Keys

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

Currently, May is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $176). Flying from Portland, Maine to Florida Keys in March is currently the most expensive (average of $292). 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 Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated December 17, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Portland to Florida Keys to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

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 Portland to Florida Keys. 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 from for flights from Portland to Florida Keys?

    For a flight from Portland to Florida Keys, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city.

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

    Airlines like Southwest, Delta, and American Airlines fly from Portland, Maine to Florida Keys in about 6h 30m. The time it takes to get you to your destination can typically vary by up to 2h 15m. The distance from Portland, Maine to Florida Keys is about 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 Portland, Maine to Florida Keys one-way?

    The cheapest airlines for a one-way flight from Portland, Maine to Florida Keys are American Airlines ($99), Southwest ($108), and Delta ($108).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Florida Keys 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 Portland, Maine to Florida Keys?

    Currently, May is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $176). Flying from Portland, Maine to Florida Keys in March is currently the most expensive (average of $292). 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

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Alternative routes for Portland to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Portland to Florida Keys

Discover the top 3 airlines that operate flights from Portland to Florida Keys. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$436FlexibilityNo cancel feeOn-time71%
DeltaCheapest$268Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$326Average$578FlexibilityNo cancel feeOn-time69%

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