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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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$208
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$399
From Portland to Florida Keys
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One-way flight from Portland to Florida Keys
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Highest demand for flights based on searches. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 7/22:49 pmPWM - MIA
1 stop6h 00mAmerican Airlines
Wed 7/99:59 amMIA - PWM
1 stop6h 44mAmerican Airlines
Deal found 6/11$208
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/112:55 pmPWM - MIA
1 stop8h 21mDelta
Fri 7/43:29 pmMIA - PWM
1 stop8h 01mDelta
Deal found 6/10$217
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/85:35 amPWM - MIA
2 stops11h 06mUnited Airlines
Tue 7/156:22 amMIA - PWM
1 stop6h 58mUnited Airlines
Deal found 6/10$222
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Sat 11/111:29 amPWM - EYW
2 stops7h 38mAmerican Airlines
Tue 11/42:54 pmEYW - PWM
1 stop7h 34mAmerican Airlines
Deal found 6/10$314
This Southwest deal was found by Cheapflights users on 6/12. 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.
Wed 8/65:50 amPWM - MIA
2 stops10h 30mSouthwest
Sun 8/108:05 amMIA - PWM
1 stop8h 45mSouthwest
Deal found 6/12$317
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:55 pmPWM - EYW
1 stop6h 44mDelta
Tue 7/86:27 pmEYW - PWM
1 stop6h 11mDelta
Deal found 6/11$406
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/276:00 amPWM - EYW
1 stop6h 41mUnited Airlines
Tue 7/12:12 pmEYW - PWM
2 stops9h 47mUnited Airlines
Deal found 6/11$415
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2510:23 amPWM - MIA
2 stops37h 19mMultiple Airlines
Sun 6/2912:32 pmMIA - PWM
2 stops22h 51mMultiple Airlines
Deal found 6/10$563
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/198:07 pmPWM - EYW
2 stops20h 31mMultiple Airlines
Wed 6/254:49 pmEYW - PWM
2 stops27h 23mMultiple Airlines
Deal found 6/11$771
This Gotogate deal was found by Cheapflights users on 6/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/138:52 pmPWM - EYW
2 stops36h 30mBreeze Airways
Thu 7/1710:02 amEYW - PWM
3 stops28h 05mBreeze Airways
Deal found 6/11$809

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 June 12, 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

Wed 7/2

2:49 pm-8:49 pm

1 stop6h 00m

Miami

Wed 7/9

9:59 am-4:43 pm

1 stop6h 44m

$208

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 7/1

12:55 pm-9:16 pm

1 stop8h 21m

Miami

Fri 7/4

3:29 pm-11:30 pm

1 stop8h 01m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 7/8

5:35 am-4:41 pm

2 stops11h 06m

Miami

Tue 7/15

6:22 am-1:20 pm

1 stop6h 58m

$222

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 11/1

11:29 am-7:07 pm

2 stops7h 38m

Key West

Tue 11/4

2:54 pm-10:28 pm

1 stop7h 34m

$314

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 8/6

5:50 am-4:20 pm

2 stops10h 30m

Miami

Sun 8/10

8:05 am-4:50 pm

1 stop8h 45m

$317

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/3

12:55 pm-7:39 pm

1 stop6h 44m

Key West

Tue 7/8

6:27 pm-12:38 am

1 stop6h 11m

$406

PortlandKey West

PWM - EYW

PWMEYW

Portland

Fri 6/27

6:00 am-12:41 pm

1 stop6h 41m

Key West

Tue 7/1

2:12 pm-11:59 pm

2 stops9h 47m

$415

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 6/25

10:23 am-11:42 pm

2 stops37h 19m

Miami

Sun 6/29

12:32 pm-11:23 am

2 stops22h 51m

$563

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sun 7/13

8:52 pm-9:22 am

2 stops36h 30m

Key West

Thu 7/17

10:02 am-2:07 pm

3 stops28h 05m

$809

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 6/25

12:38 pm-4:42 pm

2 stops28h 04m

Key West

Sun 6/29

2:07 pm-5:36 pm

3 stops27h 29m

$845

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 19 results
1
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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 $493). 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.

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 June 12, 2025.
To help decide which airline to fly from Portland to Florida Keys, see what other customers have to say about Breeze Airways, Alaska Airlines and Southwest. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Alaska Airlines
8.0
Very good
10,000 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,287 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,946 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 ($109), United Airlines ($114), and Delta ($160).

  • 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 $493). 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$381FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$372Average$578FlexibilityNo cancel feeOn-time69%

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