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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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Delta)

One-way from

$109
(American Airlines)

Popular in

July

Cheapest in

September

Average price

$388
Provider with most accurate pricing for Portland-Miami flight deals.
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Provider most trusted by Cheapflights users for Portland-Miami flights.
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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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 12/612:12 pmPWM - MIA
1 stop6h 38mDelta
Wed 12/107:12 amMIA - PWM
1 stop6h 42mDelta
Deal found 10/30$217
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/86:08 amPWM - MIA
1 stop8h 37mDelta
Mon 12/153:39 pmMIA - PWM
1 stop8h 20mDelta
Deal found 10/29$218
This Delta deal was found by Cheapflights users on 10/28. 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 11/124:40 pmPWM - MIA
1 stop6h 03mDelta
Mon 11/177:00 amMIA - PWM
1 stop5h 30mDelta
Deal found 10/28$237
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 12/156:00 amPWM - MIA
1 stop6h 24mDelta
Mon 12/155:20 pmMIA - PWM
1 stop6h 39mDelta
Deal found 10/28$248
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/256:00 amPWM - MIA
1 stop8h 37mUnited Airlines
Tue 12/27:05 amMIA - PWM
1 stop7h 17mUnited Airlines
Deal found 10/28$262
This Delta deal was found by Cheapflights users on 10/29. 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 11/194:40 pmPWM - MIA
1 stop6h 03mDelta
Wed 11/263:40 pmMIA - PWM
1 stop6h 39mDelta
Deal found 10/29$268
This United Airlines deal was found by Cheapflights users on 10/29. 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 12/96:00 amPWM - EYW
1 stop7h 51mUnited Airlines
Sat 12/132:42 pmEYW - PWM
1 stop8h 30mUnited Airlines
Deal found 10/29$269
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 12/95:34 amPWM - EYW
2 stops9h 20mAmerican Airlines
Sat 12/132:36 pmEYW - PWM
1 stop7h 56mAmerican Airlines
Deal found 10/30$274
This Delta deal was found by Cheapflights users on 10/30. 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 12/34:43 pmPWM - MIA
1 stop6h 09mDelta
Thu 12/117:12 amMIA - PWM
1 stop6h 42mDelta
Deal found 10/30$278
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 12/86:00 amPWM - MIA
2 stops10h 54mUnited Airlines
Thu 12/114:36 pmMIA - PWM
1 stop6h 33mUnited Airlines
Deal found 10/29$284
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/155:34 amPWM - MIA
2 stops7h 00mAmerican Airlines
Mon 12/153:27 pmMIA - PWM
1 stop6h 10mAmerican Airlines
Deal found 10/28$288
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/1312:23 pmPWM - MIA
1 stop8h 22mAmerican Airlines
Sat 12/206:38 pmMIA - PWM
1 stop5h 10mAmerican Airlines
Deal found 10/29$289

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 October 30, 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 1/14

2:35 pm-8:54 pm

1 stop6h 19m

Miami

Fri 1/16

5:40 pm-12:20 am

1 stop6h 40m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 12/6

12:12 pm-6:50 pm

1 stop6h 38m

Miami

Fri 12/12

4:55 pm-10:23 pm

1 stop5h 28m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 12/6

12:12 pm-6:50 pm

1 stop6h 38m

Miami

Wed 12/10

7:12 am-1:54 pm

1 stop6h 42m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 12/10

12:53 pm-9:50 pm

1 stop8h 57m

Miami

Mon 12/15

3:39 pm-11:59 pm

1 stop8h 20m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 11/12

4:40 pm-10:43 pm

1 stop6h 03m

Miami

Mon 11/17

7:00 am-12:30 pm

1 stop5h 30m

$237

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 11/12

6:00 am-2:35 pm

1 stop8h 35m

Miami

Tue 11/18

4:52 pm-10:19 pm

1 stop5h 27m

$237

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 11/25

6:00 am-2:37 pm

1 stop8h 37m

Miami

Tue 12/2

7:05 am-2:22 pm

1 stop7h 17m

$262

PortlandMiami

PWM - MIA

PWMMIA

Portland

Thu 11/20

6:00 am-12:22 pm

1 stop6h 22m

Miami

Wed 11/26

3:40 pm-10:19 pm

1 stop6h 39m

$268

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 12/9

5:34 am-4:57 pm

2 stops11h 23m

Key West

Sat 12/13

2:36 pm-10:32 pm

1 stop7h 56m

$274

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 1/14

5:30 am-1:48 pm

1 stop8h 18m

Key West

Wed 1/21

7:10 am-5:16 pm

2 stops10h 06m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 35 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, September is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $179). 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 October 30, 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
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,906 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Delta and American Airlines fly from Portland, Maine to Florida Keys in about 6h 19m. The time it takes to get you to your destination can typically vary by up to 5h 04m. 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 ($109), Breeze Airways ($140), and Delta ($174).

  • 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, September is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $179). 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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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$439FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$373Average$578FlexibilityNo cancel feeOn-time69%

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