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$109+ Cheap flights from Florida Keys to Portland, ME (PWM)

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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Florida Keys to Portland

Keep the following information in mind while searching for Florida Keys to Portland flight deals. Data was last updated June 12, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$109
(Delta)

Popular in

August

Cheapest in

July

Average price

$489
From Florida Keys to Portland
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One-way flight from Florida Keys to Portland
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Highest demand for flights based on searches. 9% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($36 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 Florida Keys to Portland

Cheapest flights from Florida Keys to Portland
Explore the most affordable flight options available from Florida Keys to Portland. 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 6/12. 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.
Fri 9/194:35 pmMIA - PWM
1 stop6h 30mAmerican Airlines
Mon 9/227:05 amPWM - MIA
1 stop7h 35mAmerican Airlines
Deal found 6/12$217
This Delta deal was found by Cheapflights users on 6/9. 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 9/47:00 amMIA - PWM
1 stop6h 56mDelta
Sun 9/76:00 amPWM - MIA
1 stop8h 01mDelta
Deal found 6/9$248
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.
Fri 9/53:45 pmEYW - PWM
1 stop6h 44mAmerican Airlines
Mon 9/86:00 amPWM - EYW
1 stop8h 00mAmerican Airlines
Deal found 6/11$269
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.
Thu 7/315:44 pmMIA - PWM
1 stop5h 30mUnited Airlines
Sun 8/35:35 amPWM - MIA
1 stop6h 14mUnited Airlines
Deal found 6/10$272
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/115:10 pmMIA - PWM
1 stop6h 55mSouthwest
Mon 7/145:40 amPWM - MIA
1 stop10h 40mSouthwest
Deal found 6/10$284
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.
Wed 9/106:20 pmEYW - PWM
1 stop5h 43mDelta
Fri 9/1912:30 pmPWM - EYW
1 stop7h 14mDelta
Deal found 6/10$323
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.
Thu 6/2612:32 pmMIA - PWM
2 stops23h 13mMultiple Airlines
Mon 6/3012:16 pmPWM - MIA
2 stops29h 44mMultiple Airlines
Deal found 6/10$418
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Wed 9/106:45 pmEYW - PWM
2 stops28h 16mUnited Airlines
Wed 9/176:14 amPWM - EYW
3 stops35h 51mUnited Airlines
Deal found 6/9$547
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/109:47 amEYW - PWM
3 stops52h 04mBreeze Airways
Fri 9/192:36 pmPWM - EYW
3 stops43h 43mBreeze Airways
Deal found 6/10$719
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 6/262:07 pmEYW - PWM
3 stops27h 29mMultiple Airlines
Mon 6/306:16 pmPWM - EYW
2 stops15h 06mMultiple Airlines
Deal found 6/11$773

Cheapflights Fare Finder

Customize your flight search to find flights from Florida Keys to Portland 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 Florida Keys to Portland that are best for you.

Fly from

Florida Keys

Fly to

Portland

Route

Depart

Return

Price

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 7/10

4:45 pm-11:19 pm

1 stop6h 34m

Portland

Thu 7/17

6:01 pm-12:37 am

1 stop6h 36m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 7/23

5:10 pm-11:25 pm

1 stop6h 15m

Portland

Tue 7/29

5:30 am-3:40 pm

2 stops10h 10m

$222

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 9/4

7:00 am-1:56 pm

1 stop6h 56m

Portland

Sun 9/7

6:00 am-2:01 pm

1 stop8h 01m

$248

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 9/5

3:45 pm-10:29 pm

1 stop6h 44m

Portland

Mon 9/8

6:00 am-2:00 pm

1 stop8h 00m

$269

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 7/31

5:44 pm-11:14 pm

1 stop5h 30m

Portland

Sun 8/3

5:35 am-11:49 am

1 stop6h 14m

$272

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/10

6:20 pm-12:03 am

1 stop5h 43m

Portland

Fri 9/19

12:30 pm-7:44 pm

1 stop7h 14m

$323

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 6/26

12:32 pm-11:45 am

2 stops23h 13m

Portland

Mon 6/30

12:16 pm-6:00 pm

2 stops29h 44m

$418

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/10

6:45 pm-11:01 pm

2 stops28h 16m

Portland

Wed 9/17

6:14 am-6:05 pm

3 stops35h 51m

$547

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/10

9:47 am-1:51 pm

3 stops52h 04m

Portland

Fri 9/19

2:36 pm-10:19 am

3 stops43h 43m

$719

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 6/26

2:07 pm-5:36 pm

3 stops27h 29m

Portland

Mon 6/30

6:16 pm-9:22 am

2 stops15h 06m

$773

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 19 results
1
2

Best time to book a flight from Florida Keys to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Florida Keys 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 Florida Keys to Portland

What is the cheapest month to book a flight from Florida Keys to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Florida Keys to Portland, Maine (average of $296). Flying from Florida Keys to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland by month

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

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, Maine, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated June 12, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest and Delta from Florida Keys to Portland to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Entertainment

6.6

Boarding

8.3

Overall

8.1

Comfort

8.2

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

Food

6.7

Entertainment

6.6

Boarding

8.3

Overall

8.1

Comfort

8.2

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

Food

6.7

Entertainment

6.6

Boarding

8.3

Overall

8.1

Comfort

8.2

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

Food

6.7

Entertainment

6.6

Boarding

8.3

Overall

8.1

Comfort

8.2

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

Food

6.7

Entertainment

6.6

Boarding

8.3

Overall

8.1

Comfort

8.2

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!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Entertainment

6.6

Boarding

8.3

Overall

8.1

Comfort

8.2

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 Florida Keys to Portland. 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 into for flights to Portland from Florida Keys?

    Portland (PWM) is the airport you will fly into if you book a flight from Florida Keys to Portland. It is only a 2.9 mi journey from Portland (PWM) to Portland’s city center.

  • What are the cheapest airlines to fly from Florida Keys to Portland, Maine one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $109. United Airlines flights start at $114 while deals on Sun Country Air start at $176 one-way.

  • Can I find deals for flights from Florida Keys to Portland that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Portland.

  • Can I find deals for business class flights from Florida Keys to Portland?

    Yes. Cheapflights offers flight deals from Florida Keys to Portland 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 Florida Keys to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Florida Keys to Portland, Maine (average of $296). Flying from Florida Keys to Portland, Maine in July is currently the most expensive (average of $394). 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

Traveling to a place near Florida Keys?

Book flights to Florida Keys if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Florida Keys to Portland

Discover the top airline that operate flights from Florida Keys to Portland. 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
American AirlinesCheapest$258Average$336FlexibilityNo cancel feeOn-time71%

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