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 12/24. 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
Typical prices: $277-$342
Delta
Tue 1/13Tue 1/20
MIA - PWM • 1 stop
Cheapest one-way
$109
Typical prices: $172-$309
Delta
Wed 12/24
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

Tue, Jan 13 - Tue, Jan 20
Delta Logo
5:35 pm - 12:26 am
MIA
-
PWM
6h 51m1 stop
Delta Logo
2:35 pm - 11:20 pm
PWM
-
MIA
8h 45m1 stop
$217Delta
Thu, Jan 8 - Mon, Jan 12
American Airlines Logo
6:26 am - 12:06 pm
MIA
-
PWM
5h 40m1 stop
American Airlines Logo
12:40 pm - 9:10 pm
PWM
-
MIA
8h 30m2 stops
$222American Airlines
Thu, Jan 22 - Wed, Jan 28
Delta Logo
2:45 pm - 10:27 pm
EYW
-
PWM
7h 42m1 stop
Delta Logo
6:00 am - 12:48 pm
PWM
-
EYW
6h 48m1 stop
$257Delta
Thu, Jan 22 - Wed, Jan 28
Delta Logo
2:45 pm - 10:27 pm
EYW
-
PWM
7h 42m1 stop
Delta Logo
6:00 am - 5:11 pm
PWM
-
EYW
11h 11m2 stops
$262Delta
Sat, Feb 14 - Tue, Feb 17
American Airlines Logo
9:50 am - 4:43 pm
MIA
-
PWM
6h 53m1 stop
American Airlines Logo
5:03 pm - 10:52 pm
PWM
-
MIA
5h 49m1 stop
$265American Airlines
Wed, Jan 21 - Tue, Jan 27
American Airlines Logo
7:08 am - 3:31 pm
EYW
-
PWM
8h 23m2 stops
American Airlines Logo
12:40 pm - 9:47 pm
PWM
-
EYW
9h 07m2 stops
$267American Airlines
Fri, Jan 23 - Wed, Jan 28
Delta Logo
2:45 pm - 10:27 pm
EYW
-
PWM
7h 42m1 stop
Delta Logo
6:00 am - 12:48 pm
PWM
-
EYW
6h 48m1 stop
$277Delta
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
7:15 am - 1:56 pm
MIA
-
PWM
6h 41m1 stop
United Airlines Logo
3:12 pm - 10:20 pm
PWM
-
MIA
7h 08m1 stop
$297United Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
1:45 pm - 11:30 pm
MIA
-
PWM
9h 45m2 stops
United Airlines Logo
3:12 pm - 10:20 pm
PWM
-
MIA
7h 08m1 stop
$302United Airlines
Wed, Jan 21 - Wed, Jan 28
Breeze Airways Logo
10:49 am - 5:38 pm
EYW
-
PWM
6h 49m1 stop
Breeze Airways Logo
11:02 am - 9:26 am
PWM
-
EYW
22h 24m1 stop
$331Breeze Airways
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 3% 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.
7.9
SouthwestOverall score based on 4250 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

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.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

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.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

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