PWM

$72 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 12/2. 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

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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

Thu, Dec 11 - Wed, Jan 7
Delta Logo
8:05 am - 4:06 pmMIA-PWM
8h 01m1 stop
Delta Logo
6:30 am - 3:09 pmPWM-MIA
8h 39m1 stop
$227Delta
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Wed, Jan 7 - Sat, Jan 10
American Airlines Logo
6:35 am - 2:01 pmMIA-PWM
7h 26m1 stop
American Airlines Logo
1:22 pm - 8:38 pmPWM-MIA
7h 16m2 stops
$232American Airlines
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Fri, Dec 12 - Sat, Jan 10
Delta Logo
8:05 am - 4:06 pmMIA-PWM
8h 01m1 stop
Delta Logo
6:00 am - 2:48 pmPWM-MIA
8h 48m1 stop
$237Delta
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Fri, Nov 7 - Mon, Nov 10
Southwest Logo
6:00 am - 11:10 amMIA-PWM
5h 10m1 stop
Southwest Logo
5:30 am - 6:55 pmPWM-MIA
13h 25m2 stops
$242Southwest
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Thu, Nov 6 - Mon, Nov 10
American Airlines Logo
4:18 pm - 11:59 pmEYW-PWM
7h 41m2 stops
American Airlines Logo
5:43 am - 5:51 pmPWM-EYW
12h 08m2 stops
$279American Airlines
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Fri, Dec 12 - Fri, Jan 9
Southwest Logo
6:00 am - 11:10 amMIA-PWM
5h 10m1 stop
Southwest Logo
12:45 pm - 10:00 pmPWM-MIA
9h 15m2 stops
$303Southwest
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Thu, Oct 9 - Mon, Nov 10
United Airlines Logo
3:12 pm - 11:13 pmEYW-PWM
8h 01m1 stop
United Airlines Logo
6:00 am - 2:04 pmPWM-EYW
8h 04m1 stop
$309United Airlines
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Fri, Sep 26 - Mon, Sep 29
United Airlines Logo
12:27 pm - 9:44 pmMIA-PWM
9h 17m1 stop
United Airlines Logo
6:00 am - 2:17 pmPWM-MIA
8h 17m1 stop
$389United Airlines
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Thu, Oct 9 - Thu, Nov 6
Breeze Airways Logo
8:55 am - 9:06 amEYW-PWM
24h 11m1 stop
Breeze Airways Logo
3:15 pm - 9:17 amPWM-EYW
18h 02m2 stops
$415Breeze Airways
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Sun, Sep 28 - Thu, Oct 2
Breeze Airways Logo
8:55 am - 9:06 amEYW-PWM
24h 11m1 stop
Breeze Airways Logo
3:15 pm - 9:17 amPWM-EYW
18h 02m2 stops
$673Breeze Airways
Find Deal

Everything you should know

Cheapest round-trip
$227
Typical prices: $411-615
Delta
Thu 12/11Wed 1/7
MIA - PWM • 1 stop
Cheapest one-way
$72
Typical prices: $243-363
Southwest
Tue 12/2
MIA - PWM • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$72
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 3% 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 4242 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

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

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

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.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

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

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Crew professional. Easy bag drop off. On time. Good entertainment.

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