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Florida Keys

$125+ Cheap flights from Portland (PDX) to Florida Keys

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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheap flight deals from Portland to Florida Keys

Keep the following information in mind while searching for Portland to Florida Keys flight deals. Data was last updated June 18, 2025.

Round-trip from

$249
(Delta)

One-way from

$125
(Delta)

Popular in

December

Cheapest in

August

Average price

$478
From Portland to Florida Keys
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One-way flight from Portland to Florida Keys
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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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 Portland to Florida Keys

Cheapest flights from Portland to Florida Keys
Explore the most affordable flight options available from Portland to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This Delta deal was found by Cheapflights users on 6/17. 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.
Tue 7/1512:40 amPDX - MIA
1 stop9h 58mDelta
Wed 7/236:34 pmMIA - PDX
1 stop8h 01mDelta
Deal found 6/17$249
This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/123:10 pmPDX - MIA
1 stop11h 28mSpirit Airlines
Sun 7/207:00 amMIA - PDX
1 stop29h 18mSpirit Airlines
Deal found 6/17$250
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/159:15 pmPDX - MIA
2 stops15h 25mSouthwest
Tue 7/226:15 amMIA - PDX
1 stop11h 55mSouthwest
Deal found 6/16$260
This FlightHub deal was found by Cheapflights users on 6/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/45:50 pmPDX - MIA
1 stop9h 40mMultiple Airlines
Sun 7/68:55 pmMIA - PDX
1 stop17h 22mMultiple Airlines
Deal found 6/16$278
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/228:37 pmPDX - MIA
1 stop17h 54mAlaska Airlines
Fri 9/266:31 pmMIA - PDX
2 stops14h 46mAlaska Airlines
Deal found 6/16$282
This FlightHub deal was found by Cheapflights users on 6/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:01 pmPDX - MIA
1 stop8h 29mFrontier
Wed 7/236:00 amMIA - PDX
1 stop20h 24mFrontier
Deal found 6/16$285
This United Airlines deal was found by Cheapflights users on 6/16. 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 7/18:50 amPDX - MIA
2 stops10h 49mUnited Airlines
Fri 7/46:35 pmMIA - PDX
1 stop8h 55mUnited Airlines
Deal found 6/16$288
This American Airlines deal was found by Cheapflights users on 6/16. 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 11/811:13 pmPDX - MIA
Nonstop5h 37mAmerican Airlines
Sun 11/237:30 pmMIA - PDX
Nonstop6h 37mAmerican Airlines
Deal found 6/16$338
This Sun Country Air deal was found by Cheapflights users on 6/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:36 pmPDX - MIA
1 stop13h 21mSun Country Air
Sun 11/1611:53 amMIA - PDX
1 stop8h 49mSun Country Air
Deal found 6/16$385
This American Airlines deal was found by Cheapflights users on 6/17. 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 10/49:56 pmPDX - EYW
1 stop11h 09mAmerican Airlines
Tue 10/143:52 pmEYW - PDX
1 stop8h 03mAmerican Airlines
Deal found 6/17$389
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 8/211:00 pmPDX - EYW
1 stop8h 51mDelta
Wed 8/66:27 pmEYW - PDX
2 stops17h 45mDelta
Deal found 6/16$413
This Mytrip deal was found by Cheapflights users on 6/17. 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 7/183:10 pmPDX - EYW
2 stops20h 58mMultiple Airlines
Mon 7/2110:23 amEYW - PDX
2 stops25h 55mMultiple Airlines
Deal found 6/17$436

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Florida Keys 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 18, 2025.
Use the filters below to find and compare flights from Portland to Florida Keys that are best for you.

Fly from

Portland

Fly to

Florida Keys

Route

Depart

Return

Price

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 7/15

12:40 am-1:38 pm

1 stop9h 58m

Miami

Wed 7/23

6:34 pm-11:35 pm

1 stop8h 01m

$249

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 7/12

3:10 pm-5:38 am

1 stop11h 28m

Miami

Sun 7/20

7:00 am-9:18 am

1 stop29h 18m

$250

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 7/15

9:15 pm-3:40 pm

2 stops15h 25m

Miami

Tue 7/22

6:15 am-3:10 pm

1 stop11h 55m

$260

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 7/4

5:50 pm-6:30 am

1 stop9h 40m

Miami

Sun 7/6

8:55 pm-11:17 am

1 stop17h 22m

$278

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 9/22

8:37 pm-5:31 pm

1 stop17h 54m

Miami

Fri 9/26

6:31 pm-6:17 am

2 stops14h 46m

$282

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 7/15

7:01 pm-6:30 am

1 stop8h 29m

Miami

Wed 7/23

6:00 am-11:24 pm

1 stop20h 24m

$285

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 7/1

8:50 am-10:39 pm

2 stops10h 49m

Miami

Fri 7/4

6:35 pm-12:30 am

1 stop8h 55m

$288

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 11/8

11:13 pm-7:50 am

Nonstop5h 37m

Miami

Sun 11/23

7:30 pm-11:07 pm

Nonstop6h 37m

$338

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 11/7

6:36 pm-10:57 am

1 stop13h 21m

Miami

Sun 11/16

11:53 am-5:42 pm

1 stop8h 49m

$385

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 10/4

9:56 pm-12:05 pm

1 stop11h 09m

Key West

Tue 10/14

3:52 pm-8:55 pm

1 stop8h 03m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Showing 1-10 of 26 results
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Best time to book a flight from Portland to Florida Keys

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

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

Currently, August is the cheapest month in which you can book a flight from Portland to Florida Keys (average of $328). Flying from Portland to Florida Keys in March is currently the most expensive (average of $493). 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 Florida Keys by month

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

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

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

If weather is an important factor for your trip to Florida Keys, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated June 18, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Portland to Florida Keys. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,965 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,809 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Food

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Portland to Florida Keys. 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 from for flights from Portland to Florida Keys?

    Located just 6.0 mi from the city center, Portland (PDX) is the airport most travelers will use when flying to Florida Keys from Portland.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $125. However, be on the lookout for offers from Southwest and Spirit Airlines, as they are both options that can get you from Portland to Florida Keys for a low price.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Portland to Florida Keys (average of $328). Flying from Portland to Florida Keys in March is currently the most expensive (average of $493). 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

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Alternative routes for Portland to Florida Keys

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Top 3 airlines flying from Portland to Florida Keys

Discover the top 3 airlines that operate flights from Portland to Florida Keys. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$428FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$275Average$568FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$317Average$622FlexibilityNo cancel feeOn-time69%

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