HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$97+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Florida Keys with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(Mytrip)

One-way from

$97
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$505
Provider with most accurate pricing for Portland-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Miami flights.
Search Deals
From Portland to Florida Keys
Search Deals
One-way flight from Portland to Florida Keys
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($105 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 February 22, 2025.

This Mytrip deal was found by Cheapflights users on 2/21. 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.
Mon 3/106:18 pmPWM - MIA
3 stops26h 22mMultiple Airlines
Fri 3/149:43 amMIA - PWM
1 stop7h 27mMultiple Airlines
Deal found 2/21$269
This American Airlines deal was found by Cheapflights users on 2/22. 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 3/185:25 amPWM - EYW
1 stop5h 48mAmerican Airlines
Tue 3/256:20 pmEYW - PWM
1 stop5h 27mAmerican Airlines
Deal found 2/22$269
This American Airlines deal was found by Cheapflights users on 2/21. 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 5/161:59 pmPWM - MIA
1 stop6h 15mAmerican Airlines
Tue 5/207:06 amMIA - PWM
1 stop8h 30mAmerican Airlines
Deal found 2/21$275
This Delta deal was found by Cheapflights users on 2/22. 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 3/104:30 pmPWM - MIA
1 stop6h 06mDelta
Sat 3/157:00 amMIA - PWM
1 stop5h 36mDelta
Deal found 2/22$282
This United Airlines deal was found by Cheapflights users on 2/21. 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 3/186:10 amPWM - MIA
1 stop7h 16mUnited Airlines
Thu 5/16:15 amMIA - PWM
2 stops11h 14mUnited Airlines
Deal found 2/21$286
This JetBlue deal was found by Cheapflights users on 2/20. 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.
Sat 4/55:35 pmPWM - MIA
1 stop6h 16mJetBlue
Fri 4/112:08 pmMIA - PWM
1 stop8h 52mJetBlue
Deal found 2/20$300
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 3/315:50 amPWM - MIA
2 stops11h 50mSouthwest
Sat 4/57:30 amMIA - PWM
2 stops9h 30mSouthwest
Deal found 2/20$338
This Delta deal was found by Cheapflights users on 2/20. 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 3/35:34 amPWM - EYW
1 stop6h 04mDelta
Tue 3/116:15 pmEYW - PWM
1 stop5h 43mDelta
Deal found 2/20$354
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 3/87:20 pmPWM - EYW
2 stops13h 50mUnited Airlines
Wed 3/1912:45 pmEYW - PWM
2 stops10h 30mUnited Airlines
Deal found 2/20$406

Find flights from Portland to Florida Keys within your budget

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 February 22, 2025.

Fly from

Portland

Fly to

Florida Keys

Route

Depart

Return

Price

PortlandMiami

PWM - MIA

PWMMIA

Portland

Mon 3/10

6:18 pm-8:40 pm

3 stops26h 22m

Miami

Fri 3/14

9:43 am-5:10 pm

1 stop7h 27m

$269

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/18

5:25 am-11:13 am

1 stop5h 48m

Key West

Tue 3/25

6:20 pm-11:47 pm

1 stop5h 27m

$269

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 5/16

1:59 pm-8:14 pm

1 stop6h 15m

Miami

Tue 5/20

7:06 am-3:36 pm

1 stop8h 30m

$275

PortlandMiami

PWM - MIA

PWMMIA

Portland

Mon 3/10

4:30 pm-10:36 pm

1 stop6h 06m

Miami

Sat 3/15

7:00 am-12:36 pm

1 stop5h 36m

$282

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 3/18

6:10 am-1:26 pm

1 stop7h 16m

Miami

Thu 5/1

6:15 am-5:29 pm

2 stops11h 14m

$286

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 4/5

5:35 pm-11:51 pm

1 stop6h 16m

Miami

Fri 4/11

2:08 pm-11:00 pm

1 stop8h 52m

$300

PortlandMiami

PWM - MIA

PWMMIA

Portland

Mon 3/31

5:50 am-5:40 pm

2 stops11h 50m

Miami

Sat 4/5

7:30 am-5:00 pm

2 stops9h 30m

$338

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 3/3

5:34 am-11:38 am

1 stop6h 04m

Key West

Tue 3/11

6:15 pm-11:58 pm

1 stop5h 43m

$354

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 3/8

7:20 pm-9:10 am

2 stops13h 50m

Key West

Wed 3/19

12:45 pm-11:15 pm

2 stops10h 30m

$406

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 3/21

5:50 pm-3:34 pm

1 stop21h 44m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 15 results
1
2

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.

Travel insights for flights from Portland to Florida Keys

Get recent, data-driven insights about flights from Portland to Florida Keys including ideal travel times, pricing trends, and more.

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 $510). 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 February 22, 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 February 22, 2025.
To help decide which airline to fly from Portland to Florida Keys, see what other customers have to say about Southwest, Alaska Airlines and Delta. 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
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 JetBlue ($98), Delta ($129), and United Airlines ($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, 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 $510). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Orlando flights
Boston to West Palm Beach flights
Boston to Tampa flights
Boston to Fort Myers flights
Boston to Sarasota flights
Boston to Jacksonville flights
Boston to Key West flights
Portland to Orlando flights
Boston to Pensacola flights
Portland to Miami flights
Boston to St Petersburg flights
Boston to Panama City flights
Boston to Daytona Beach flights
Boston to Gainesville flights
Portland to Tampa flights
Portland to West Palm Beach flights
Portland to Fort Lauderdale flights
Boston to Valparaiso flights
Boston to Orlando Sanford Intl flights
Boston to Melbourne flights
Portland to Fort Myers flights
Bangor to Orlando Sanford Intl flights
Portland to Sarasota flights
Bangor to Orlando flights
Boston to Punta Gorda flights
Portland to Key West flights
Portland to Jacksonville flights
Bangor to Jacksonville flights
Boston to Tallahassee flights
Portland to Pensacola flights
Bangor to Tampa flights
Bangor to St Petersburg flights
Bangor to Fort Lauderdale flights
Bangor to West Palm Beach flights
Bangor to Miami flights
Portland to Panama City flights
Portland to Daytona Beach flights
Bangor to Key West flights
Bangor to Pensacola flights
Bangor to Fort Myers flights
Bangor to Sarasota flights
Augusta to Orlando flights
Augusta to Tampa flights
Portland to Valparaiso flights
Portland to Melbourne flights
Rockland to Orlando flights
Augusta to Fort Myers flights
Bangor to Valparaiso flights

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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$431FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$438FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$345Average$588FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.