$98 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 4/25. 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

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Florida Keys.
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Cheap Flights from Portland to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$214
Key West
Key West1 stop$444
Miami
Miami1 stop$214
Key West
Key West1 stop$444

Book Cheap Portland to Florida Keys Plane Tickets

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Florida Keys

Mon, Apr 6 - Wed, Apr 8
Southwest Logo
11:55 pm - 2:15 pm
PDX
-
MIA
11h 20m
2 stops
Southwest Logo
6:40 am - 12:30 pm
MIA
-
PDX
8h 50m
1 stop
$214Southwest
Tue, Apr 28 - Thu, May 7
Frontier Logo
12:38 pm - 5:05 am
PDX
-
MIA
13h 27m
1 stop
Frontier Logo
9:41 pm - 7:51 pm
MIA
-
PDX
25h 10m
1 stop
$215Frontier
Tue, Apr 14 - Mon, Apr 20
Multiple Airlines Logo
1:48 pm - 5:05 am
PDX
-
MIA
12h 17m
1 stop
Multiple Airlines Logo
7:00 am - 11:52 am
MIA
-
PDX
55h 52m
2 stops
$218Multiple Airlines
Tue, Apr 28 - Wed, May 6
Frontier Logo
12:38 pm - 5:05 am
PDX
-
MIA
13h 27m
1 stop
Frontier Logo
7:00 pm - 4:46 pm
MIA
-
PDX
24h 46m
2 stops
$219Frontier
Mon, Apr 6 - Wed, Apr 15
Southwest Logo
11:55 pm - 11:55 am
PDX
-
MIA
9h 00m
1 stop
Southwest Logo
6:40 am - 8:45 pm
MIA
-
PDX
17h 05m
2 stops
$220Southwest
Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
12:38 pm - 5:05 am
PDX
-
MIA
13h 27m
1 stop
Multiple Airlines Logo
2:09 pm - 11:03 am
MIA
-
PDX
47h 54m
2 stops
$223Multiple Airlines
Wed, Apr 22 - Wed, Apr 29
United Airlines Logo
11:15 pm - 1:31 pm
PDX
-
EYW
11h 16m
1 stop
United Airlines Logo
3:52 pm - 10:34 pm
EYW
-
PDX
9h 42m
1 stop
$444United Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
6:00 am - 5:02 pm
PDX
-
EYW
8h 02m
1 stop
American Airlines Logo
2:29 pm - 9:38 pm
EYW
-
PDX
10h 09m
1 stop
$457American Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
7:00 am - 10:58 pm
PDX
-
EYW
12h 58m
2 stops
American Airlines Logo
2:29 pm - 9:38 pm
EYW
-
PDX
10h 09m
1 stop
$462American Airlines
Sat, Apr 25 - Wed, Apr 29
United Airlines Logo
11:15 pm - 1:31 pm
PDX
-
EYW
11h 16m
1 stop
United Airlines Logo
3:52 pm - 10:34 pm
EYW
-
PDX
9h 42m
1 stop
$489United Airlines
Booking Insights

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 time of day to fly to Florida Keys?

The average price for all round-trip flights from Portland to Florida Keys depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida Keys is generally in the morning, when round-trip flights cost $459 on average. The most expensive time of day to fly to Florida Keys is generally at night, which is peak travel time and where the average cost of a ticket is $643.

Can I save money by flying with a layover from Portland to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $378, prices are generally cheapest when you fly direct.

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 $296 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $535 and $447 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.

Your flight ticket price will generally be cheaper if you fly to Florida Keys on a Tuesday and more expensive on a Saturday. On your return trip to Portland, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

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 3 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$98
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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.

Reviews of the 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.
7.9
Alaska AirlinesOverall score based on 12052 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.1Food
7.0Entertainment
Airline reviews

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

2.0 MediocreAnonymous, Mar 2026
PDX - SEA
Read more Alaska Airlines reviews

Never got on because first part of trip was cancelled and we have no idea when we will get rebooked…

Wonderful as always! Pleasant staff, smooth ride, and timely departure.

Everything ran like it should. Staff was professional. Looking forward to flying with them again.

Liked the attention and speed when getting wheelchair..........Was assured by phone that my needs would be taken care of and they were with my name.

The seats were spacious and comfortable. Even in basic economy. However, the flight boarded 30 minutes late.

Alaska used to be a top notch airline. With it's growth it is now in line with the big airlines. Not bad, not great.

Great. I did have a little issue getting into the Lounge, which is likely more an American Airlines issue. I did not carry my physical AAdvantage Executive credit card with me on this trip, which Admirals Club membership is a part of the benefits of having this card. The instructions on the AA website and the Citi cards website make it seem like you don't need the physical card, as both sites state you can enter with your boarding pass and driver's license. But both lounges said you were required to present the physical card (and not the digital version, via Apple Pay), as only the physical card says "Admirals Club" on the back.I also do not have a physical Admirals Club membership card, so while both lounges eventually let me in, both denied me entrance initially for this reason.

Everything from the time I booked my flight through to the end when I got home was smooth and wonderful. Service was great, the flight attendants were attentive and there were no outstanding delays.

Delayed and no entertainment? I also forgot my headphones and immediately reported it and have not heard back yet.

The crew was very friendly. Boarding was quick and efficient.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

I couldn’t make my first flight due to weather delays trapping us in the town we were in. Then I had to buy a new ticket

Much better than Spirit. I was please by the easy fast check in and boarding

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

The flight was really crowded. Flight attendants were just ok.

Didn't get a seat assignment until the last minute even though i picked a seat.

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

Better than expected. Staff were friendly and nice on both flights.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports