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Florida Keys

$96+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap 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 August 13, 2025.

Round-trip from

$204
(American Airlines)

One-way from

$96
(American Airlines)

Popular in

July

Cheapest in

September

Average price

$296
From Portland to Florida Keys
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One-way flight from Portland to Florida Keys
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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 13, 2025.

This American Airlines deal was found by Cheapflights users on 8/11. 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 9/31:02 pmPWM - MIA
1 stop6h 57mAmerican Airlines
Fri 9/54:01 pmMIA - PWM
1 stop7h 44mAmerican Airlines
Deal found 8/11$204
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/272:06 pmPWM - MIA
1 stop6h 39mAmerican Airlines
Sat 8/303:45 pmMIA - PWM
1 stop6h 00mAmerican Airlines
Deal found 8/12$208
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 10/251:20 pmPWM - MIA
2 stops8h 30mSouthwest
Tue 10/287:35 amMIA - PWM
1 stop5h 45mSouthwest
Deal found 8/12$209
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/128:25 amPWM - MIA
1 stop7h 55mSouthwest
Sun 9/148:05 amMIA - PWM
1 stop8h 45mSouthwest
Deal found 8/12$217
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/278:40 amPWM - MIA
1 stop7h 46mAmerican Airlines
Sat 10/410:16 amMIA - PWM
1 stop6h 34mAmerican Airlines
Deal found 8/12$218
This American Airlines deal was found by Cheapflights users on 8/10. 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 9/251:09 pmPWM - MIA
1 stop5h 28mAmerican Airlines
Thu 10/24:00 pmMIA - PWM
1 stop7h 05mAmerican Airlines
Deal found 8/10$219
This American Airlines deal was found by Cheapflights users on 8/12. 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 11/55:19 pmPWM - MIA
1 stop5h 34mAmerican Airlines
Mon 11/106:55 pmMIA - PWM
1 stop4h 43mAmerican Airlines
Deal found 8/12$244
This Delta deal was found by Cheapflights users on 8/12. 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.
Sat 11/82:38 pmPWM - MIA
1 stop8h 41mDelta
Sat 11/155:59 pmMIA - PWM
1 stop5h 52mDelta
Deal found 8/12$257
This American Airlines deal was found by Cheapflights users on 8/12. 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 11/85:19 pmPWM - MIA
2 stops7h 29mAmerican Airlines
Sat 11/152:32 pmMIA - PWM
1 stop7h 12mAmerican Airlines
Deal found 8/12$262
This American Airlines deal was found by Cheapflights users on 8/11. 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 8/2511:21 amPWM - MIA
1 stop5h 06mAmerican Airlines
Fri 9/194:00 pmMIA - PWM
1 stop7h 05mAmerican Airlines
Deal found 8/11$278
This American Airlines deal was found by Cheapflights users on 8/11. 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 12/115:53 amPWM - EYW
1 stop7h 53mAmerican Airlines
Mon 12/155:19 pmEYW - PWM
1 stop5h 10mAmerican Airlines
Deal found 8/11$288
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Fri 10/316:05 pmPWM - EYW
2 stops14h 57mMultiple Airlines
Wed 11/59:47 amEYW - PWM
1 stop7h 51mMultiple Airlines
Deal found 8/11$292

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 August 13, 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

Sat 10/25

12:59 pm-8:29 pm

1 stop7h 30m

Miami

Tue 10/28

6:51 pm-11:51 pm

1 stop5h 00m

$204

PortlandMiami

PWM - MIA

PWMMIA

Portland

Mon 9/8

5:10 pm-11:56 pm

1 stop6h 46m

Miami

Tue 9/16

2:47 pm-8:11 pm

1 stop5h 24m

$204

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 9/3

1:02 pm-7:59 pm

1 stop6h 57m

Miami

Fri 9/5

4:01 pm-11:45 pm

1 stop7h 44m

$204

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 8/27

2:06 pm-8:45 pm

1 stop6h 39m

Miami

Sat 8/30

3:45 pm-9:45 pm

1 stop6h 00m

$208

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 10/25

1:20 pm-9:50 pm

2 stops8h 30m

Miami

Tue 10/28

7:35 am-1:20 pm

1 stop5h 45m

$209

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 8/30

5:30 pm-12:24 am

1 stop6h 54m

Miami

Thu 9/4

4:25 pm-12:03 am

1 stop7h 38m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Thu 8/28

2:48 pm-11:17 pm

1 stop8h 29m

Miami

Sat 9/6

6:50 am-12:29 pm

1 stop5h 39m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Thu 10/23

7:44 am-3:30 pm

1 stop7h 46m

Miami

Mon 10/27

6:20 am-1:52 pm

1 stop7h 32m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 9/12

7:05 am-2:40 pm

1 stop7h 35m

Miami

Sat 9/20

10:16 am-4:50 pm

1 stop6h 34m

$217

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 1/14

5:51 am-1:55 pm

1 stop8h 04m

Key West

Wed 1/21

5:21 pm-10:29 pm

1 stop5h 08m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 34 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, August is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $328). Flying from Portland, Maine to Florida Keys in March is currently the most expensive (average of $492). 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 August 13, 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.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.2
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 ($96), Southwest ($96), and Delta ($159).

  • 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, August is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $328). Flying from Portland, Maine to Florida Keys in March is currently the most expensive (average of $492). 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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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$424FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$386FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$372Average$578FlexibilityNo cancel feeOn-time69%

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