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 1/25. 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: $327-$380
Delta
Sat 1/10Sun 1/11
MIA - PWM • 1 stop
Cheapest one-way
$109
Typical prices: $229-$367
American Airlines
Sun 1/25
MIA - PWM • 1 stop
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Flight Deals
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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

Sat, Jan 10 - Sun, Jan 11
Delta Logo
7:40 am - 1:45 pmMIA-PWM
6h 05m1 stop
Delta Logo
5:30 am - 12:14 pmPWM-MIA
6h 44m1 stop
$217Delta
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Wed, Nov 12 - Thu, Nov 20
Delta Logo
6:00 am - 12:30 pmMIA-PWM
6h 30m1 stop
Delta Logo
6:00 am - 12:22 pmPWM-MIA
6h 22m1 stop
$237Delta
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Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
7:00 am - 2:12 pmMIA-PWM
7h 12m1 stop
United Airlines Logo
6:00 am - 6:17 pmPWM-MIA
12h 17m2 stops
$242United Airlines
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Wed, Nov 26 - Wed, Dec 3
United Airlines Logo
6:05 am - 1:36 pmMIA-PWM
7h 31m1 stop
United Airlines Logo
3:20 pm - 11:59 pmPWM-MIA
8h 39m1 stop
$263United Airlines
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Fri, Nov 14 - Sun, Nov 16
Delta Logo
5:15 pm - 11:54 pmMIA-PWM
6h 39m1 stop
Delta Logo
6:00 am - 2:35 pmPWM-MIA
8h 35m1 stop
$268Delta
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Tue, Dec 9 - Wed, Dec 17
American Airlines Logo
9:30 am - 4:28 pmMIA-PWM
6h 58m2 stops
American Airlines Logo
12:23 pm - 8:11 pmPWM-MIA
7h 48m1 stop
$273American Airlines
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Thu, Jan 8 - Mon, Jan 12
American Airlines Logo
12:00 pm - 11:43 pmEYW-PWM
11h 43m2 stops
American Airlines Logo
5:20 am - 2:54 pmPWM-EYW
9h 34m2 stops
$279American Airlines
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Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
10:00 pm - 5:38 pmMIA-PWM
19h 38m2 stops
Multiple Airlines Logo
11:29 am - 6:59 pmPWM-MIA
7h 30m1 stop
$316Multiple Airlines
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Fri, Nov 28 - Fri, Dec 5
Southwest Logo
6:00 am - 11:10 amMIA-PWM
5h 10m1 stop
Southwest Logo
5:30 am - 11:05 amPWM-MIA
5h 35m1 stop
$413Southwest
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Sat, Jan 10 - Sun, Jan 11
Southwest Logo
6:45 am - 2:45 pmMIA-PWM
8h 00m2 stops
Southwest Logo
1:00 pm - 9:55 pmPWM-MIA
8h 55m2 stops
$423Southwest
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Good to know

Low seasonJanuary
Cheapest flight$109
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 5% 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 4241 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

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

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.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

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.

Pretty good. The food was just mediocre, the boarding and crew were good.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

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