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$144 Find Cheap Flights from Florida Keys to Portland - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Florida Keys to Portland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Florida Keys to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Florida Keys to Portland

Tue, Oct 20 - Wed, Oct 28
Delta Logo
7:40 am - 1:02 pm
EYW
-
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5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Wed, Oct 21 - Wed, Oct 28
Delta Logo
7:40 am - 1:02 pm
EYW
-
PWM
5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
5:34 pm - 11:41 pm
EYW
-
PWM
6h 07m
1 stop
American Airlines Logo
7:00 am - 1:54 pm
PWM
-
EYW
6h 54m
1 stop
$301American Airlines
Sun, Oct 18 - Thu, Oct 22
Multiple Airlines Logo
10:59 am - 9:08 am
EYW
-
PWM
22h 09m
1 stop
Multiple Airlines Logo
3:10 pm - 5:47 pm
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-
EYW
26h 37m
1 stop
$301Multiple Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
7:40 am - 1:02 pm
EYW
-
PWM
5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
4:50 pm - 9:57 pm
MIA
-
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5h 07m
1 stop
American Airlines Logo
6:00 am - 11:19 am
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-
MIA
5h 19m
1 stop
$309American Airlines
Tue, Oct 20 - Fri, Oct 30
American Airlines Logo
2:15 pm - 9:51 pm
EYW
-
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7h 36m
1 stop
American Airlines Logo
12:06 pm - 6:49 pm
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EYW
6h 43m
1 stop
$335American Airlines
Fri, Aug 28 - Mon, Aug 31
Multiple Airlines Logo
3:30 pm - 4:16 pm
MIA
-
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24h 46m
1 stop
Multiple Airlines Logo
7:00 am - 11:05 pm
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MIA
16h 05m
2 stops
$339Multiple Airlines
Tue, Sep 1 - Wed, Sep 9
Southwest Logo
9:15 am - 9:10 pm
MIA
-
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11h 55m
2 stops
Southwest Logo
5:45 am - 4:05 pm
PWM
-
MIA
10h 20m
2 stops
$349Southwest
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
7:45 am - 9:05 pm
MIA
-
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13h 20m
2 stops
Southwest Logo
5:40 am - 1:35 pm
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MIA
7h 55m
1 stop
$370Southwest
Useful Info

Good to know

Low season

January

Cheapest flight

$144
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Miami to Portland

FAQs for booking flights from Florida Keys to Portland

  • How does KAYAK find such low prices on flights from Florida Keys to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Florida Keys to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida Keys to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Florida Keys is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Florida Keys to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Florida Keys with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida Keys to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Florida Keys to Portland

 
Need help choosing which airline to fly with from Florida Keys to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4226 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Boarding was quick and i made my connection early due to early arrival time

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

My flight was delayed and I got back around 3.5 hours later than expected. I had to get a new connecting flight

I had only one problem. The temperature on the flight was too COLD. I froze throughout the flight. I thought it might be only my problem but when I went to the restroom during the flight, I saw several people huddling in their jackets. A couple had their winter coats on and I was jealous since I had only a very light jacket.

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

As I said I never took the flight back from due to earlier delayed that prevented from taking the second trip back and nobody helped me to rebook from kayak

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

90 min delay for a food cart that needed to be fixed.

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