$100 Find Cheap Flights from Portland to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Florida Keys departing on 5/28. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Florida Keys, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Florida Keys, as well as popular online travel agencies
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Flights Deals

Best Florida Keys Flight Deals from Portland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Miami
Miami1 stop$193
Key West
Key West1 stop$269
Miami
Miami1 stop$193
Key West
Key West1 stop$269

Cheap Flights from Portland to Florida Keys

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Florida Keys 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.

Recent round-trip flight deals from Portland to Florida Keys

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Portland to Florida Keys.
Discover the best prices for you by selecting your travel dates on KAYAK.
JetBlue Logo
7:12 am - 1:31 pmPWM-MIA
6h 19m1 stop
JetBlue Logo
7:00 am - 2:40 pmMIA-PWM
7h 40m1 stop
$193JetBlue
Find Deal
Sun, May 25 - Thu, May 29
JetBlue Logo
7:12 am - 1:15 pmPWM-MIA
6h 03m1 stop
JetBlue Logo
2:30 pm - 11:00 pmMIA-PWM
8h 30m1 stop
$201JetBlue
Find Deal
Tue, May 13 - Tue, May 20
American Airlines Logo
6:00 am - 1:38 pmPWM-MIA
7h 38m1 stop
American Airlines Logo
6:35 am - 1:22 pmMIA-PWM
6h 47m1 stop
$208American Airlines
Find Deal
Tue, May 20 - Wed, May 28
Delta Logo
2:30 pm - 11:19 pmPWM-MIA
8h 49m1 stop
Delta Logo
3:24 pm - 12:14 amMIA-PWM
8h 50m1 stop
$217Delta
Find Deal
Sat, May 17 - Fri, May 30
United Airlines Logo
3:43 pm - 9:51 pmPWM-MIA
6h 08m1 stop
United Airlines Logo
1:29 pm - 11:27 pmMIA-PWM
9h 58m2 stops
$222United Airlines
Find Deal
Tue, May 13 - Wed, May 14
Delta Logo
6:28 pm - 12:57 amPWM-MIA
6h 29m1 stop
Delta Logo
6:05 am - 1:54 pmMIA-PWM
7h 49m1 stop
$234Delta
Find Deal
Sat, Jun 14 - Sat, Jun 21
American Airlines Logo
5:56 am - 11:21 amPWM-MIA
5h 25m1 stop
American Airlines Logo
6:59 am - 4:08 pmMIA-PWM
9h 09m1 stop
$255American Airlines
Find Deal
Fri, Sep 19 - Sun, Sep 21
United Airlines Logo
6:00 am - 12:51 pmPWM-MIA
6h 51m1 stop
United Airlines Logo
5:22 pm - 11:27 pmMIA-PWM
6h 05m1 stop
$297United Airlines
Find Deal
Wed, May 14 - Wed, May 14
Southwest Logo
8:45 am - 8:45 pmPWM-MIA
12h 00m2 stops
Southwest Logo
7:35 am - 1:15 pmMIA-PWM
5h 40m1 stop
$352Southwest
Find Deal
Fri, Sep 12 - Mon, Sep 15
Southwest Logo
5:50 am - 2:45 pmPWM-MIA
8h 55m2 stops
Southwest Logo
6:10 pm - 11:20 pmMIA-PWM
5h 10m1 stop
$380Southwest
Find Deal
Mon, May 26 - Fri, May 30
Useful Info

KAYAK's insights & trends for Portland to Florida Keys flights

Get data-powered insights and trends into flights from Portland to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Portland to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Florida Keys, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Florida Keys is September, when tickets cost $285 (return) on average. On the other hand, the most expensive months are April and February, when the average cost of round-trip tickets is $541 and $505 respectively.

What’s the cheapest day of the week to fly from Portland to Florida Keys?

The average price of all round-trip flights from Portland to Florida Keys clicked on KAYAK for each day over the last 12 months.

When flying from Portland to Florida Keys, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Portland to Florida Keys?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Florida Keys, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.


Good to know

Low seasonJune
High seasonApril
Cheapest flight$100
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Portland to Miami

FAQs - booking Florida Keys flights

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

    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 Portland to Florida Keys.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to 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 Portland to Florida Keys?

    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 from Portland to Florida Keys with an airline and back with another airline.

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

    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 from Portland to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida Keys?

    The cheapest time of day to fly to Florida Keys is generally in the afternoon, when round-trip flights cost $438 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the morning, which is peak travel time and where the average cost of a ticket is $486.

Top 5 airlines serving from Portland to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Portland to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Florida Keys? 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 4294 reviews
7.6Entertainment
7.1Food
8.6Crew
8.0Comfort
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

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.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

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.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

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.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

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

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

A bit rush for transit. Food and entertainment are not available

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

The inflight system with their wifi is a hot mess and doesn't work. Separately they do, but when you try to do theoretically simple things like pair a device for control it all falls apart

It was too hot in the cabin. The AC did not help.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

Overall was excellent. Will definitely us JetBlue in the future.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

I like their airplanes because they have plenty of legroom in their seats they always work with me if I have a change of plans on my tickets courteous and I always feel safe flying with them.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

The flight crew that we had in our section may have been tired or something. I asked the flight attendant about my son’s screen not working and she spoke down to me like I was stupid. He still had no working screen throughout his flight. The other members had no personality and seemed like they were annoyed when you asked them for something. Definitely took a hit for simple things on my JB experience.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Would have thought that they would gas up plane before everyone got on board

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Standard. No different than a discount carrier on a short trip.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Checking in at the counter was very disappointing. The lady had a very bad attitude and smart at me. She had no smile, did not greet me by name, or acknowledge me as a valued customer. Poor reflection of the airline.

Miami lounges were overcrowded and we were unable to get in. We only had a short time. But the banks are too tight in all American hubs

I was pleasantly surprised with an upgrade at boarding. I finally had a mostly gluten free food options and a very attentive attendant.

Very poor. Our special services attendant gave us incorrect information. I also was mishandled at landing. There was no wheelchair waiting. I fell deboarding the plane. Appalling!

Everything you need to know for your flight to Florida Keys

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