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Florida Keys

$100+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(Delta)

One-way from

$100
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$558
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. 7% potential increase in price ($35 potential increase over avg. RT price).
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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 April 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 April 1, 2025.

This Delta deal was found by Cheapflights users on 4/1. 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 5/106:35 amPWM - MIA
1 stop7h 35mDelta
Fri 5/163:24 pmMIA - PWM
1 stop8h 50mDelta
Deal found 4/1$227
This JetBlue deal was found by Cheapflights users on 4/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:12 amPWM - MIA
1 stop6h 19mJetBlue
Tue 6/37:00 amMIA - PWM
1 stop7h 40mJetBlue
Deal found 4/1$236
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/25:18 pmPWM - MIA
1 stop6h 14mAmerican Airlines
Tue 5/68:28 amMIA - PWM
1 stop4h 54mAmerican Airlines
Deal found 4/1$239
This United Airlines deal was found by Cheapflights users on 4/1. 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 5/26:00 amPWM - MIA
1 stop8h 26mUnited Airlines
Tue 5/66:15 amMIA - PWM
2 stops11h 14mUnited Airlines
Deal found 4/1$256
This American Airlines deal was found by Cheapflights users on 3/31. 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 8/96:07 amPWM - EYW
1 stop5h 16mAmerican Airlines
Tue 8/125:09 pmEYW - PWM
1 stop4h 57mAmerican Airlines
Deal found 3/31$269
This Southwest deal was found by Cheapflights users on 4/1. 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 6/73:55 pmPWM - MIA
1 stop7h 40mSouthwest
Sun 6/155:35 amMIA - PWM
1 stop6h 40mSouthwest
Deal found 4/1$309
This Delta deal was found by Cheapflights users on 3/31. 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 5/101:30 pmPWM - EYW
1 stop6h 37mDelta
Thu 5/156:25 pmEYW - PWM
1 stop5h 34mDelta
Deal found 3/31$343
This United Airlines deal was found by Cheapflights users on 3/31. 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 4/156:00 amPWM - EYW
1 stop9h 04mUnited Airlines
Sat 4/196:45 pmEYW - PWM
2 stops20h 08mUnited Airlines
Deal found 3/31$528
This Mytrip deal was found by Cheapflights users on 3/31. 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.
Sat 5/310:23 amPWM - EYW
2 stops30h 26mMultiple Airlines
Thu 5/810:23 amEYW - PWM
3 stops24h 47mMultiple Airlines
Deal found 3/31$721
This Mytrip deal was found by Cheapflights users on 3/31. 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 4/98:12 pmPWM - MIA
3 stops35h 41mMultiple Airlines
Sun 4/135:45 amMIA - PWM
3 stops29h 56mMultiple Airlines
Deal found 3/31$937

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 April 1, 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 5/10

6:35 am-2:10 pm

1 stop7h 35m

Miami

Fri 5/16

3:24 pm-12:14 am

1 stop8h 50m

$227

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 5/27

7:12 am-1:31 pm

1 stop6h 19m

Miami

Tue 6/3

7:00 am-2:40 pm

1 stop7h 40m

$236

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 5/2

5:18 pm-11:32 pm

1 stop6h 14m

Miami

Tue 5/6

8:28 am-1:22 pm

1 stop4h 54m

$239

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 5/2

6:00 am-2:26 pm

1 stop8h 26m

Miami

Tue 5/6

6:15 am-5:29 pm

2 stops11h 14m

$256

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/10

6:00 am-4:40 pm

2 stops10h 40m

Key West

Thu 5/15

5:24 pm-11:06 pm

1 stop5h 42m

$274

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 6/7

3:55 pm-11:35 pm

1 stop7h 40m

Miami

Sun 6/15

5:35 am-12:15 pm

1 stop6h 40m

$309

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/10

1:30 pm-8:07 pm

1 stop6h 37m

Key West

Thu 5/15

6:25 pm-11:59 pm

1 stop5h 34m

$343

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 4/15

6:00 am-3:04 pm

1 stop9h 04m

Key West

Sat 4/19

6:45 pm-2:53 pm

2 stops20h 08m

$528

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/3

10:23 am-4:49 pm

2 stops30h 26m

Key West

Thu 5/8

10:23 am-11:10 am

3 stops24h 47m

$721

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 4/15

6:07 pm-8:58 pm

2 stops26h 51m

Miami

Sun 4/20

1:53 pm-11:41 am

3 stops21h 48m

$1,118

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 16 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.

What is the cheapest time of day to fly from PWM to EOA?

Find hourly flight availability from Portland to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2025.

When flying from Portland, Maine to Florida Keys, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 April 1, 2025.
To help decide which airline to fly from Portland to Florida Keys, see what other customers have to say about Southwest, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 ($100), JetBlue ($139), and United Airlines ($154).

  • 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$425FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$346Average$588FlexibilityNo cancel feeOn-time69%

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