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Florida Keys

$106+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:48 am
PDX
-
MIA
1 stop14h 17m
Frontier
Sat 4/256:30 am
MIA
-
PDX
1 stop8h 12m
Frontier
Deal found 1/26$215
This Delta deal was found by Cheapflights users on 1/26. 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.
Fri 2/205:10 pm
PDX
-
MIA
1 stop10h 25m
Delta
Tue 2/246:24 pm
MIA
-
PDX
1 stop8h 51m
Delta
Deal found 1/26$216
This Delta deal was found by Cheapflights users on 1/26. 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.
Fri 4/244:35 pm
PDX
-
MIA
1 stop10h 20m
Delta
Wed 4/297:10 am
MIA
-
PDX
1 stop11h 28m
Delta
Deal found 1/26$217
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/169:44 pm
PDX
-
MIA
1 stop7h 44m
American Airlines
Tue 2/245:00 am
MIA
-
PDX
1 stop9h 07m
American Airlines
Deal found 1/25$219
This Southwest deal was found by Cheapflights users on 1/26. 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.
Mon 3/1611:55 pm
PDX
-
MIA
1 stop8h 45m
Southwest
Tue 4/712:10 pm
MIA
-
PDX
2 stops11h 50m
Southwest
Deal found 1/26$220
This Southwest deal was found by Cheapflights users on 1/27. 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 3/36:30 am
PDX
-
MIA
1 stop12h 00m
Southwest
Sat 3/75:15 am
MIA
-
PDX
1 stop7h 55m
Southwest
Deal found 1/27$221
This Southwest deal was found by Cheapflights users on 1/27. 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.
Mon 4/1311:55 pm
PDX
-
MIA
1 stop9h 00m
Southwest
Tue 4/216:40 am
MIA
-
PDX
2 stops17h 05m
Southwest
Deal found 1/27$226
This American Airlines deal was found by Cheapflights users on 1/27. 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 11/145:42 pm
PDX
-
MIA
1 stop8h 31m
American Airlines
Sun 11/228:19 pm
MIA
-
PDX
Nonstop6h 32m
American Airlines
Deal found 1/27$227
This Southwest deal was found by Cheapflights users on 1/27. 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 5/85:10 am
PDX
-
MIA
1 stop14h 40m
Southwest
Tue 5/121:25 pm
MIA
-
PDX
2 stops12h 35m
Southwest
Deal found 1/27$228
This Orbitz deal was found by Cheapflights users on 1/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:00 am
PDX
-
MIA
Nonstop5h 44m
Multiple Airlines
Tue 4/217:50 am
MIA
-
PDX
1 stop8h 12m
Multiple Airlines
Deal found 1/26$229
This Southwest deal was found by Cheapflights users on 1/26. 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.
Sun 4/125:20 am
PDX
-
MIA
1 stop14h 25m
Southwest
Tue 4/216:40 am
MIA
-
PDX
2 stops17h 05m
Southwest
Deal found 1/26$231
This Travelocity deal was found by Cheapflights users on 1/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:00 am
PDX
-
MIA
Nonstop5h 44m
Multiple Airlines
Wed 4/228:42 am
MIA
-
PDX
1 stop27h 17m
Multiple Airlines
Deal found 1/26$234

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$215
(Frontier)

One-way from

$106
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$387
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. 10% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 28, 2026.
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 3/10

11:15 pm-10:15 am

1 stop8h 00m

Miami

Thu 3/19

5:56 pm-11:59 pm

1 stop9h 03m

$235

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/17

5:40 pm-6:49 am

1 stop10h 09m

Miami

Tue 3/24

5:56 pm-11:59 pm

1 stop9h 03m

$235

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 2/28

10:00 am-12:20 am

1 stop11h 20m

Miami

Wed 3/4

2:00 pm-10:15 pm

1 stop11h 15m

$236

PortlandMiami

PDX - MIA

PDXMIA

Portland

Thu 2/19

5:30 am-5:19 pm

1 stop8h 49m

Miami

Tue 2/24

6:24 pm-12:15 am

1 stop8h 51m

$247

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 5/10

11:55 pm-12:10 pm

1 stop9h 15m

Miami

Sat 5/16

9:30 am-5:45 pm

2 stops11h 15m

$266

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sat 6/6

5:30 am-5:32 pm

1 stop9h 02m

Miami

Mon 6/15

6:05 pm-11:53 pm

1 stop8h 48m

$268

PortlandMiami

PDX - MIA

PDXMIA

Portland

Sun 2/15

5:30 am-5:14 pm

1 stop8h 44m

Miami

Thu 2/19

7:50 am-4:10 pm

1 stop11h 20m

$275

PortlandMiami

PDX - MIA

PDXMIA

Portland

Mon 3/2

7:00 am-3:44 pm

Nonstop5h 44m

Miami

Fri 3/6

5:59 pm-11:44 pm

1 stop8h 45m

$287

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 3/10

11:55 pm-2:25 pm

2 stops11h 30m

Miami

Thu 3/19

6:05 pm-12:45 am

1 stop9h 40m

$297

PortlandMiami

PDX - MIA

PDXMIA

Portland

Tue 2/24

5:05 am-6:35 pm

2 stops10h 30m

Miami

Fri 2/27

6:10 am-2:55 pm

1 stop11h 45m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 29 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, 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 January 28, 2026.
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
11,799 reviews

Boarding

8.1

Food

7.1

Entertainment

7.0

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,799 reviews
Alaska Airlines
8.0
Very good
11,799 reviews

Boarding

8.1

Food

7.1

Entertainment

7.0

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,120 reviews
Alaska Airlines
8.0
Very good
11,799 reviews

Boarding

8.1

Food

7.1

Entertainment

7.0

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,829 reviews
Alaska Airlines
8.0
Very good
11,799 reviews

Boarding

8.1

Food

7.1

Entertainment

7.0

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,206 reviews
Alaska Airlines
8.0
Very good
11,799 reviews

Boarding

8.1

Food

7.1

Entertainment

7.0

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,198 reviews
Alaska Airlines
8.0
Very good
11,799 reviews

Boarding

8.1

Food

7.1

Entertainment

7.0

Comfort

7.8

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 8h. Delta provides one of the quickest options available for as low as $235. 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 American Airlines, with whom users have recently found tickets for as low as $100. However, be on the lookout for offers from Frontier 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Portland to Florida Keys

Discover the top 2 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$595FlexibilityNo cancel feeOn-time71%

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