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$101+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Delta)

One-way from

$101
(JetBlue)
Provider with most accurate pricing for Key West-Portland flight deals.
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Provider most trusted by Cheapflights users for Key West-Portland flights.
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From Florida Keys to Portland
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One-way flight from Florida Keys to Portland
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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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 7/33:55 pmMIA - PWM
1 stop8h 31mDelta
Tue 7/86:53 pmPWM - MIA
1 stop6h 02mDelta
Deal found 4/30$217
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/165:22 pmMIA - PWM
1 stop6h 05mUnited Airlines
Sun 5/185:30 amPWM - MIA
2 stops9h 26mUnited Airlines
Deal found 4/30$222
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 6/134:54 pmEYW - PWM
1 stop6h 09mAmerican Airlines
Mon 6/166:00 amPWM - EYW
1 stop7h 48mAmerican Airlines
Deal found 4/30$269
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/162:30 pmMIA - PWM
1 stop8h 29mJetBlue
Sun 5/187:12 amPWM - MIA
1 stop6h 19mJetBlue
Deal found 4/30$277
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/117:35 amMIA - PWM
1 stop5h 40mSouthwest
Thu 8/1410:35 amPWM - MIA
2 stops11h 10mSouthwest
Deal found 4/29$340
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/156:25 pmEYW - PWM
1 stop5h 34mDelta
Mon 5/195:30 amPWM - EYW
1 stop5h 21mDelta
Deal found 4/30$349
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 7/274:45 pmMIA - PWM
1 stop6h 14mAmerican Airlines
Sun 8/36:01 pmPWM - MIA
1 stop5h 29mAmerican Airlines
Deal found 4/30$361
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/62:29 pmMIA - PWM
3 stops21h 24mMultiple Airlines
Sun 6/83:30 pmPWM - MIA
2 stops22h 40mMultiple Airlines
Deal found 4/30$473
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 5/152:18 pmEYW - PWM
2 stops9h 41mUnited Airlines
Mon 5/195:30 amPWM - EYW
2 stops12h 35mUnited Airlines
Deal found 4/30$502

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 May 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

Thu 7/3

3:55 pm-12:26 am

1 stop8h 31m

Portland

Tue 7/8

6:53 pm-12:55 am

1 stop6h 02m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Fri 5/16

5:22 pm-11:27 pm

1 stop6h 05m

Portland

Sun 5/18

5:30 am-2:56 pm

2 stops9h 26m

$222

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 6/13

4:54 pm-11:03 pm

1 stop6h 09m

Portland

Mon 6/16

6:00 am-1:48 pm

1 stop7h 48m

$269

MiamiPortland

MIA - PWM

MIAPWM

Miami

Fri 5/16

2:30 pm-10:59 pm

1 stop8h 29m

Portland

Sun 5/18

7:12 am-1:31 pm

1 stop6h 19m

$277

MiamiPortland

MIA - PWM

MIAPWM

Miami

Mon 8/11

7:35 am-1:15 pm

1 stop5h 40m

Portland

Thu 8/14

10:35 am-9:45 pm

2 stops11h 10m

$340

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 5/15

6:25 pm-11:59 pm

1 stop5h 34m

Portland

Mon 5/19

5:30 am-10:51 am

1 stop5h 21m

$349

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sun 7/27

4:45 pm-10:59 pm

1 stop6h 14m

Portland

Sun 8/3

6:01 pm-11:30 pm

1 stop5h 29m

$361

MiamiPortland

MIA - PWM

MIAPWM

Miami

Fri 6/6

2:29 pm-11:53 am

3 stops21h 24m

Portland

Sun 6/8

3:30 pm-2:10 pm

2 stops22h 40m

$473

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 5/15

2:18 pm-11:59 pm

2 stops9h 41m

Portland

Mon 5/19

5:30 am-6:05 pm

2 stops12h 35m

$502

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 5/14

7:00 am-2:40 pm

1 stop7h 40m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 17 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 May is currently the most expensive (average of $405). 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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines 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.
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 JetBlue, which is currently one of the cheapest options available, starting at $101. Delta flights start at $109 while deals on United Airlines start at $140 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 May is currently the most expensive (average of $405). 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

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Alternative routes for Florida Keys to Portland

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$392FlexibilityNo cancel feeOn-time71%

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