HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$102+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida Keys to Portland 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 Florida Keys to Portland

Keep the following information in mind while searching for Florida Keys to Portland flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$257
(Delta)

One-way from

$102
(Mytrip)
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

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 February 20, 2025.

This JetBlue deal was found by Cheapflights users on 2/18. 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.
Tue 4/152:19 pmMIA - PWM
1 stop8h 41mJetBlue
Tue 4/225:35 pmPWM - MIA
1 stop6h 18mJetBlue
Deal found 2/18$216
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Mon 4/147:01 amMIA - PWM
1 stop5h 04mAmerican Airlines
Thu 4/247:20 amPWM - MIA
1 stop8h 53mAmerican Airlines
Deal found 2/18$250
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.
Thu 3/68:22 amMIA - PWM
1 stop8h 22mDelta
Thu 3/136:15 amPWM - MIA
1 stop8h 22mDelta
Deal found 2/20$257
This United Airlines deal was found by Cheapflights users on 2/18. 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 4/151:27 pmMIA - PWM
2 stops10h 00mUnited Airlines
Tue 4/226:00 amPWM - MIA
1 stop8h 55mUnited Airlines
Deal found 2/18$286
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Tue 4/1510:34 amMIA - PWM
3 stops32h 53mMultiple Airlines
Tue 4/226:07 pmPWM - MIA
2 stops28h 15mMultiple Airlines
Deal found 2/18$304
This Southwest deal was found by Cheapflights users on 2/18. 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.
Sat 4/197:45 amMIA - PWM
2 stops15h 40mSouthwest
Tue 4/296:15 amPWM - MIA
1 stop5h 40mSouthwest
Deal found 2/18$398

Find flights from Florida Keys to Portland within your budget

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 February 20, 2025.

Fly from

Florida Keys

Fly to

Portland

Route

Depart

Return

Price

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 4/15

2:19 pm-11:00 pm

1 stop8h 41m

Portland

Tue 4/22

5:35 pm-11:53 pm

1 stop6h 18m

$216

MiamiPortland

MIA - PWM

MIAPWM

Miami

Mon 4/14

7:01 am-12:05 pm

1 stop5h 04m

Portland

Thu 4/24

7:20 am-4:13 pm

1 stop8h 53m

$250

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 3/6

8:22 am-4:44 pm

1 stop8h 22m

Portland

Thu 3/13

6:15 am-2:37 pm

1 stop8h 22m

$257

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 4/15

1:27 pm-11:27 pm

2 stops10h 00m

Portland

Tue 4/22

6:00 am-2:55 pm

1 stop8h 55m

$286

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 4/15

10:34 am-7:27 pm

3 stops32h 53m

Portland

Tue 4/22

6:07 pm-10:22 pm

2 stops28h 15m

$304

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sat 4/19

7:45 am-11:25 pm

2 stops15h 40m

Portland

Tue 4/29

6:15 am-11:55 am

1 stop5h 40m

$398

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 4/10

5:57 pm-12:23 am

1 stop6h 26m

$129

MiamiPortland

MIA - PWM

MIAPWM

Miami

Thu 4/10

8:15 am-11:20 pm

2 stops15h 05m

$139

MiamiPortland

MIA - PWM

MIAPWM

Miami

Sat 3/22

6:45 am-12:30 pm

1 stop5h 45m

$164

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 4/1

6:15 pm-11:58 pm

1 stop5h 43m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Florida Keys to Portland

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

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 April is currently the most expensive (average of $498). 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 February 20, 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
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

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 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 $129. Southwest flights start at $139 while deals on American Airlines start at $164 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 April is currently the most expensive (average of $498). 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

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

Alternative routes for Florida Keys to Portland

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

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$392FlexibilityNo cancel feeOn-time71%
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.