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$100+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(American Airlines)

One-way from

$100
(American Airlines)
Provider with most accurate pricing for Key West-Portland flight deals.
Search Deals
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 April 3, 2025.

This American Airlines deal was found by Cheapflights users on 4/2. 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 5/177:20 amMIA - PWM
1 stop7h 52mAmerican Airlines
Sat 5/242:05 pmPWM - MIA
1 stop7h 00mAmerican Airlines
Deal found 4/2$199
This United Airlines deal was found by Cheapflights users on 4/2. 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 8/2612:27 pmMIA - PWM
1 stop9h 32mUnited Airlines
Sat 8/303:15 pmPWM - MIA
1 stop7h 41mUnited Airlines
Deal found 4/2$297
This Southwest deal was found by Cheapflights users on 4/2. 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 5/26:10 pmMIA - PWM
1 stop5h 10mSouthwest
Fri 5/95:50 amPWM - MIA
2 stops16h 10mSouthwest
Deal found 4/2$323
This American Airlines deal was found by Cheapflights users on 4/3. 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 07mAmerican Airlines
Mon 6/166:00 amPWM - EYW
1 stop7h 48mAmerican Airlines
Deal found 4/3$368
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.
Sun 5/185:45 pmMIA - PWM
1 stop5h 36mDelta
Wed 5/216:35 amPWM - MIA
1 stop7h 35mDelta
Deal found 4/1$558
This Mytrip deal was found by Cheapflights users on 4/2. 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 4/175:45 amMIA - PWM
2 stops29h 56mMultiple Airlines
Mon 4/216:18 pmPWM - MIA
3 stops35h 59mMultiple Airlines
Deal found 4/2$981

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 April 3, 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

Sat 5/17

7:20 am-3:12 pm

1 stop7h 52m

Portland

Sat 5/24

2:05 pm-9:05 pm

1 stop7h 00m

$199

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 8/26

12:27 pm-9:59 pm

1 stop9h 32m

Portland

Sat 8/30

3:15 pm-10:56 pm

1 stop7h 41m

$297

MiamiPortland

MIA - PWM

MIAPWM

Miami

Fri 5/2

6:10 pm-11:20 pm

1 stop5h 10m

Portland

Fri 5/9

5:50 am-10:00 pm

2 stops16h 10m

$323

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 6/13

4:54 pm-11:01 pm

1 stop6h 07m

Portland

Mon 6/16

6:00 am-1:48 pm

1 stop7h 48m

$368

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sun 5/18

5:45 pm-11:21 pm

1 stop5h 36m

Portland

Wed 5/21

6:35 am-2:10 pm

1 stop7h 35m

$558

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 4/17

5:45 am-11:41 am

2 stops29h 56m

Portland

Mon 4/21

6:18 pm-6:17 am

3 stops35h 59m

$981

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 5/7

8:30 am-3:12 pm

1 stop6h 42m

$100

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 5/8

5:47 pm-11:27 pm

1 stop5h 40m

$109

MiamiPortland

MIA - PWM

MIAPWM

Miami

Mon 5/19

7:00 am-2:40 pm

1 stop7h 40m

$169

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 5/8

5:24 pm-11:06 pm

1 stop5h 42m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 15 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 $416). 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 April 3, 2025.
Southwest
8.0
Very good
4,274 reviews

Food

7.1

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
4,274 reviews
Southwest
8.0
Very good
4,274 reviews

Food

7.1

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
7,897 reviews
Southwest
8.0
Very good
4,274 reviews

Food

7.1

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
8,619 reviews
Southwest
8.0
Very good
4,274 reviews

Food

7.1

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
2,920 reviews
Southwest
8.0
Very good
4,274 reviews

Food

7.1

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
4,274 reviews

Food

7.1

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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 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 American Airlines, which is currently one of the cheapest options available, starting at $100. United Airlines flights start at $109 while deals on JetBlue start at $169 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 $416). 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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$412FlexibilityNo cancel feeOn-time71%

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