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Florida Keys

$122+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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Cheap 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 December 22, 2025.

This Delta deal was found by Cheapflights users on 12/21. 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 12/315:11 pmPDX - MIA
1 stop10h 24mDelta
Tue 1/136:45 amMIA - PDX
1 stop8h 47mDelta
Deal found 12/21$277
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:49 pmPDX - MIA
Nonstop5h 43mAmerican Airlines
Sun 1/116:04 amMIA - PDX
1 stop8h 41mAmerican Airlines
Deal found 12/20$308
This Delta deal was found by Cheapflights users on 12/21. 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 12/315:11 pmPDX - MIA
1 stop10h 24mDelta
Fri 1/910:41 amMIA - PDX
1 stop12h 44mDelta
Deal found 12/21$317
This Delta deal was found by Cheapflights users on 12/21. 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 12/315:11 pmPDX - MIA
1 stop10h 24mDelta
Mon 1/125:37 pmMIA - PDX
1 stop17h 56mDelta
Deal found 12/21$323
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/313:59 pmPDX - MIA
2 stops42h 26mFrontier
Sat 1/103:11 pmMIA - PDX
1 stop23h 04mFrontier
Deal found 12/21$325
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/317:45 pmPDX - MIA
1 stop8h 51mUnited Airlines
Sun 1/116:20 amMIA - PDX
1 stop8h 58mUnited Airlines
Deal found 12/21$330
This Delta deal was found by Cheapflights users on 12/21. 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 12/3010:05 pmPDX - MIA
1 stop9h 18mDelta
Tue 1/136:45 amMIA - PDX
1 stop8h 47mDelta
Deal found 12/21$347
This Priceline deal was found by Cheapflights users on 12/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:29 pmPDX - MIA
1 stop12h 06mFrontier
Thu 12/257:05 amMIA - PDX
1 stop9h 19mFrontier
Deal found 12/19$363
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3010:52 pmPDX - MIA
1 stop9h 55mUnited Airlines
Wed 1/71:05 pmMIA - PDX
2 stops11h 07mUnited Airlines
Deal found 12/20$365
This United Airlines deal was found by Cheapflights users on 12/19. 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.
Mon 12/2911:55 pmPDX - EYW
1 stop9h 39mUnited Airlines
Thu 1/86:05 pmEYW - PDX
2 stops27h 05mUnited Airlines
Deal found 12/19$706
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/2511:55 pmPDX - EYW
1 stop9h 39mUnited Airlines
Sat 12/273:09 pmEYW - PDX
1 stop10h 30mUnited Airlines
Deal found 12/21$952
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Thu 12/2511:59 pmPDX - EYW
2 stops10h 14mAmerican Airlines
Sat 12/278:00 amEYW - PDX
2 stops13h 02mAmerican Airlines
Deal found 12/21$1,193

Find 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 December 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$223
(Southwest)

One-way from

$122
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$599
Provider with most accurate pricing for Portland-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Miami flights.
Search Deals
From Portland to Florida Keys
Search Deals
One-way flight from Portland to Florida Keys
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 22, 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 2/10

6:20 am-4:30 pm

1 stop7h 10m

Miami

Sun 2/15

7:55 am-8:15 pm

1 stop15h 20m

$223

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 2/7

5:15 pm-10:24 am

2 stops14h 09m

Miami

Sun 2/15

7:50 am-6:47 pm

2 stops13h 57m

$238

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 1/31

5:20 am-3:35 pm

1 stop7h 15m

Miami

Sun 2/1

7:55 am-1:45 pm

1 stop8h 50m

$241

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 2/24

5:30 am-9:51 pm

2 stops13h 21m

Miami

Wed 3/4

7:50 am-4:10 pm

1 stop11h 20m

$246

PortlandMiami

PDX - MIA

PDXMIA

Portland

Fri 2/6

5:25 pm-6:40 am

1 stop10h 15m

Miami

Tue 2/10

8:05 am-6:50 pm

2 stops13h 45m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 2/28

12:09 pm-10:47 pm

1 stop7h 38m

Miami

Mon 3/9

8:05 am-4:43 pm

1 stop11h 38m

$248

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 2/1

8:35 am-9:40 pm

1 stop10h 05m

Miami

Wed 2/4

6:55 am-3:40 pm

2 stops11h 45m

$262

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 2/1

1:30 pm-6:35 am

2 stops14h 05m

Miami

Thu 2/5

11:39 am-8:25 pm

1 stop11h 46m

$266

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 1/19

5:25 pm-6:35 am

1 stop10h 10m

Miami

Wed 1/21

6:43 am-6:50 pm

2 stops15h 07m

$267

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 1/24

5:15 pm-10:24 am

2 stops14h 09m

Miami

Wed 1/28

7:50 am-4:30 pm

2 stops11h 40m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 36 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, June is the cheapest month in which you can book a flight from Portland to Florida Keys (average of $242). Flying from Portland to Florida Keys in October is currently the most expensive (average of $715). 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 December 22, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian Airlines 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
11,500 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Alaska Airlines
8.0
Very good
11,500 reviews
Alaska Airlines
8.0
Very good
11,500 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Delta
7.9
Good
8,014 reviews
Alaska Airlines
8.0
Very good
11,500 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Hawaiian Airlines
7.8
Good
2,821 reviews
Alaska Airlines
8.0
Very good
11,500 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
United Airlines
7.4
Good
9,102 reviews
Alaska Airlines
8.0
Very good
11,500 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
American Airlines
7.2
Good
11,052 reviews
Alaska Airlines
8.0
Very good
11,500 reviews

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.0

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

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.

  • How long is the flight from Portland to Florida Keys?

    A quick flight from Portland to Florida Keys can take about 7h 10m. Southwest provides one of the quickest options available for as low as $223. Portland and Florida Keys are separated by a distance of 2695 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $87. However, be on the lookout for offers from Spirit Airlines and Delta, 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, June is the cheapest month in which you can book a flight from Portland to Florida Keys (average of $242). Flying from Portland to Florida Keys in October is currently the most expensive (average of $715). 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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$594FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$622FlexibilityNo cancel feeOn-time69%

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