PWM

$109 Find Cheap Flights from Florida Keys to Portland

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 2/12. 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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Everything you should know

Cheapest round-trip
$217
Overall average: $281
Delta
Fri 2/13Mon 3/9
MIA - PWM • 1 stop
Cheapest one-way
$109
Typical prices: $164-$395
Delta
Thu 2/12
MIA - PWM • 1 stop
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Flight Deals
Useful Info
Flight Deals

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

Fri, Feb 13 - Mon, Mar 9
Delta Logo
5:36 pm - 12:18 am
MIA
-
PWM
6h 42m
1 stop
Delta Logo
5:48 pm - 11:18 pm
PWM
-
MIA
5h 30m
1 stop
$217Delta
Fri, Feb 13 - Sun, Feb 22
American Airlines Logo
5:30 pm - 10:50 pm
MIA
-
PWM
5h 20m
1 stop
American Airlines Logo
5:42 am - 1:01 pm
PWM
-
MIA
7h 19m
1 stop
$275American Airlines
Tue, Jun 9 - Tue, Jun 16
Delta Logo
3:35 pm - 11:59 pm
MIA
-
PWM
8h 24m
1 stop
Delta Logo
6:50 pm - 12:56 am
PWM
-
MIA
6h 06m
1 stop
$278Delta
Fri, Feb 27 - Sun, Mar 1
Southwest Logo
5:55 am - 11:15 am
MIA
-
PWM
5h 20m
1 stop
Southwest Logo
4:50 pm - 11:15 pm
PWM
-
MIA
6h 25m
1 stop
$288Southwest
Tue, Jun 9 - Wed, Jun 17
United Airlines Logo
7:07 am - 1:42 pm
MIA
-
PWM
6h 35m
1 stop
United Airlines Logo
6:00 am - 3:09 pm
PWM
-
MIA
9h 09m
1 stop
$297United Airlines
Fri, Feb 13 - Sun, Feb 22
Delta Logo
2:46 pm - 11:06 pm
EYW
-
PWM
8h 20m
1 stop
Delta Logo
6:00 am - 12:45 pm
PWM
-
EYW
6h 45m
1 stop
$297Delta
Sat, Feb 14 - Wed, Feb 18
United Airlines Logo
5:05 pm - 11:20 pm
MIA
-
PWM
6h 15m
1 stop
United Airlines Logo
6:00 am - 5:29 pm
PWM
-
MIA
11h 29m
2 stops
$302United Airlines
Fri, Feb 13 - Mon, Mar 9
American Airlines Logo
5:30 pm - 10:50 pm
MIA
-
PWM
5h 20m
1 stop
American Airlines Logo
6:00 am - 1:22 pm
PWM
-
MIA
7h 22m
2 stops
$315American Airlines
Fri, Feb 13 - Mon, Feb 23
Breeze Airways Logo
1:06 pm - 10:17 am
EYW
-
PWM
21h 11m
1 stop
Breeze Airways Logo
5:06 pm - 12:21 pm
PWM
-
EYW
19h 15m
2 stops
$328Breeze Airways
Fri, Feb 13 - Sat, Feb 21
Breeze Airways Logo
1:06 pm - 10:17 am
EYW
-
PWM
21h 11m
1 stop
Breeze Airways Logo
6:18 pm - 10:21 am
PWM
-
EYW
16h 03m
1 stop
$331Breeze Airways
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 4% 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 4267 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

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