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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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$239
(Frontier)

One-way from

$125
(Delta)

Popular in

December

Cheapest in

August

Average price

$389
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. 4% potential increase in price ($19 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 July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/3. 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.
Wed 11/512:07 pmPDX - MIA
1 stop7h 11mAmerican Airlines
Tue 11/117:30 pmMIA - PDX
Nonstop6h 37mAmerican Airlines
Deal found 7/3$239
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:35 amPDX - MIA
1 stop20h 55mFrontier
Fri 8/17:15 amMIA - PDX
1 stop8h 36mFrontier
Deal found 7/2$241
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/173:10 pmPDX - MIA
1 stop11h 28mMultiple Airlines
Fri 7/257:15 amMIA - PDX
1 stop8h 36mMultiple Airlines
Deal found 7/3$242
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/610:23 amPDX - MIA
1 stop16h 15mSpirit Airlines
Mon 8/117:00 amMIA - PDX
1 stop10h 15mSpirit Airlines
Deal found 7/3$248
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/215:05 pmPDX - MIA
1 stop10h 22mDelta
Wed 7/237:48 amMIA - PDX
1 stop11h 08mDelta
Deal found 7/3$249
This United Airlines deal was found by Cheapflights users on 7/2. 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 8/511:59 pmPDX - MIA
1 stop8h 05mUnited Airlines
Tue 8/1212:06 pmMIA - PDX
2 stops11h 31mUnited Airlines
Deal found 7/2$254
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/229:15 pmPDX - MIA
2 stops15h 25mSouthwest
Tue 7/296:15 amMIA - PDX
1 stop11h 55mSouthwest
Deal found 7/1$285
This Delta deal was found by Cheapflights users on 7/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/306:00 amPDX - EYW
1 stop8h 32mDelta
Wed 8/66:27 pmEYW - PDX
1 stop8h 32mDelta
Deal found 7/3$309
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 9/129:56 pmPDX - EYW
1 stop10h 17mAmerican Airlines
Fri 9/1912:09 pmEYW - PDX
1 stop11h 28mAmerican Airlines
Deal found 7/2$391
This Mytrip deal was found by Cheapflights users on 7/2. 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 8/73:10 pmPDX - EYW
3 stops22h 26mMultiple Airlines
Thu 8/148:53 amEYW - PDX
2 stops25h 39mMultiple Airlines
Deal found 7/2$414

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 July 3, 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

Wed 11/5

12:07 pm-10:18 pm

1 stop7h 11m

Miami

Tue 11/11

7:30 pm-11:07 pm

Nonstop6h 37m

$239

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 7/25

6:35 am-6:30 am

1 stop20h 55m

Miami

Fri 8/1

7:15 am-12:51 pm

1 stop8h 36m

$241

PortlandMiami

PDX - MIA

PDXMIA

Portland

Thu 7/17

3:10 pm-5:38 am

1 stop11h 28m

Miami

Fri 7/25

7:15 am-12:51 pm

1 stop8h 36m

$242

PortlandMiami

PDX - MIA

PDXMIA

Portland

Wed 8/6

10:23 am-5:38 am

1 stop16h 15m

Miami

Mon 8/11

7:00 am-2:15 pm

1 stop10h 15m

$248

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 7/21

5:05 pm-6:27 am

1 stop10h 22m

Miami

Wed 7/23

7:48 am-3:56 pm

1 stop11h 08m

$249

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 8/5

11:59 pm-11:04 am

1 stop8h 05m

Miami

Tue 8/12

12:06 pm-8:37 pm

2 stops11h 31m

$254

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 7/22

9:15 pm-3:40 pm

2 stops15h 25m

Miami

Tue 7/29

6:15 am-3:10 pm

1 stop11h 55m

$285

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 7/30

6:00 am-5:32 pm

1 stop8h 32m

Key West

Wed 8/6

6:27 pm-11:59 pm

1 stop8h 32m

$309

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 9/12

9:56 pm-11:13 am

1 stop10h 17m

Key West

Fri 9/19

12:09 pm-8:37 pm

1 stop11h 28m

$391

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 8/7

3:10 pm-4:36 pm

3 stops22h 26m

Key West

Thu 8/14

8:53 am-7:32 am

2 stops25h 39m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 21 results
1
2
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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 $492). 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 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 July 3, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Portland to Florida Keys by reading reviews from past customers. 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

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

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

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

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
4,270 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

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
7,970 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

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
8,845 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Boarding

8.1

Food

7.1

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 Spirit Airlines and Southwest, 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 $492). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$428FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$570FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$317Average$622FlexibilityNo cancel feeOn-time69%

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