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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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Dec 1 — Dec 81
Mon 12/1
Mon 12/8
1 adult, Economy
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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 November 1, 2025.

This American Airlines deal was found by Cheapflights users on 10/31. 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.
Fri 12/55:52 pmMIA - PWM
1 stop5h 45mAmerican Airlines
Mon 12/85:46 amPWM - MIA
1 stop5h 24mAmerican Airlines
Deal found 10/31$216
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:30 amMIA - PWM
1 stop6h 08mUnited Airlines
Sun 12/146:00 amPWM - MIA
1 stop8h 41mUnited Airlines
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.
Fri 11/144:52 pmMIA - PWM
1 stop5h 27mDelta
Thu 11/206:00 amPWM - MIA
1 stop8h 20mDelta
Deal found 10/29$237
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:00 amMIA - PWM
1 stop7h 12mUnited Airlines
Sun 11/166:00 amPWM - MIA
2 stops12h 17mUnited Airlines
Deal found 10/30$242
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1012:50 pmMIA - PWM
2 stops10h 19mUnited Airlines
Sun 12/146:00 amPWM - MIA
1 stop8h 41mUnited Airlines
Deal found 10/30$249
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.
Wed 11/266:05 amMIA - PWM
1 stop7h 31mUnited Airlines
Wed 12/33:20 pmPWM - MIA
1 stop8h 39mUnited Airlines
Deal found 10/29$263
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.
Fri 11/145:15 pmMIA - PWM
1 stop6h 39mDelta
Sun 11/166:00 amPWM - MIA
1 stop8h 35mDelta
Deal found 10/30$268
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.
Tue 12/99:30 amMIA - PWM
2 stops6h 58mAmerican Airlines
Wed 12/1712:23 pmPWM - MIA
1 stop7h 48mAmerican Airlines
Deal found 10/28$273
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 12/105:20 pmMIA - PWM
1 stop6h 39mDelta
Wed 12/176:00 amPWM - MIA
1 stop6h 24mDelta
Deal found 10/28$278
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:26 pmMIA - PWM
2 stops22h 10mMultiple Airlines
Mon 12/811:21 amPWM - MIA
1 stop6h 15mMultiple Airlines
Deal found 10/31$279
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.
Thu 11/277:01 amMIA - PWM
1 stop7h 07mAmerican Airlines
Thu 12/45:17 pmPWM - MIA
1 stop5h 39mAmerican Airlines
Deal found 10/29$288

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 November 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$216
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$412
Provider with most accurate pricing for Key West-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Portland flights.
Search Deals
From Florida Keys to Portland
Search Deals
One-way flight from Florida Keys to Portland
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 1, 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

Wed 12/10

4:36 pm-11:09 pm

1 stop6h 33m

Portland

Sun 12/14

6:00 am-2:41 pm

1 stop8h 41m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sat 1/10

7:40 am-1:45 pm

1 stop6h 05m

Portland

Sun 1/11

5:30 am-12:14 pm

1 stop6h 44m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 12/9

12:50 pm-11:09 pm

2 stops10h 19m

Portland

Sun 12/14

6:00 am-11:36 am

1 stop5h 36m

$222

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sat 11/15

7:00 am-12:30 pm

1 stop5h 30m

Portland

Mon 11/17

2:30 pm-11:13 pm

1 stop8h 43m

$237

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sat 11/15

7:00 am-12:30 pm

1 stop5h 30m

Portland

Wed 11/19

1:25 pm-8:46 pm

1 stop7h 21m

$237

MiamiPortland

MIA - PWM

MIAPWM

Miami

Fri 11/14

5:15 pm-11:54 pm

1 stop6h 39m

Portland

Wed 11/19

6:00 am-1:02 pm

1 stop7h 02m

$237

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 11/13

8:05 am-4:07 pm

1 stop8h 02m

Portland

Mon 11/17

4:40 pm-10:43 pm

1 stop6h 03m

$237

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 11/13

7:15 am-1:50 pm

1 stop6h 35m

Portland

Wed 11/19

6:00 am-1:02 pm

1 stop7h 02m

$237

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 11/13

7:15 am-1:50 pm

1 stop6h 35m

Portland

Sat 11/15

2:30 pm-11:17 pm

1 stop8h 47m

$237

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 11/12

6:00 am-12:30 pm

1 stop6h 30m

Portland

Thu 11/20

6:00 am-12:22 pm

1 stop6h 22m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 31 results
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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, November is the cheapest month in which you can book a flight from Florida Keys to Portland, Maine (average of $173). Flying from Florida Keys to Portland, Maine in February is currently the most expensive (average of $331). 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 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 November 1, 2025.
Read through reviews of airlines operating flights from Florida Keys to Portland, such as Southwest, Delta, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

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
7,996 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

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
11,031 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

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 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.

  • How long is the flight from Florida Keys to Portland, Maine?

    There are many flights that can get you from Florida Keys to Portland, Maine in 6h 05m. Fly via United Airlines or Delta to get the fastest option. Airlines will cover a distance of 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 Florida Keys to Portland, Maine one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $109. Delta flights start at $109 while deals on Breeze Airways start at $151 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, November is the cheapest month in which you can book a flight from Florida Keys to Portland, Maine (average of $173). Flying from Florida Keys to Portland, Maine in February is currently the most expensive (average of $331). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Alternative routes for Florida Keys to Portland

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Top 2 airlines flying from Florida Keys to Portland

Discover the top 2 airlines 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 November 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$336FlexibilityNo cancel feeOn-time71%
DeltaCheapest$274Average$353FlexibilityNo cancel feeOn-timeN/A

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