$83 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 5/20. 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.
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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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$195
Key West
Key West1 stop$309
Miami
Miami1 stop$195
Key West
Key West1 stop$309

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.
 Logo
5:40 pm - 5:43 amPDX-MIA
9h 03m1 stop
 Logo
7:25 am - 12:55 pmMIA-PDX
8h 30m1 stop
Wed, Jun 4 - Mon, Jun 9
Frontier Logo
1:50 pm - 5:40 amPDX-MIA
12h 50m1 stop
Frontier Logo
6:00 am - 11:29 amMIA-PDX
8h 29m1 stop
$208Frontier
Find Deal
Thu, May 29 - Sat, May 31
Spirit Airlines Logo
1:37 pm - 5:43 amPDX-MIA
13h 06m1 stop
Spirit Airlines Logo
8:55 pm - 12:42 pmMIA-PDX
18h 47m1 stop
$217Spirit Airlines
Find Deal
Mon, May 19 - Wed, May 21
American Airlines Logo
10:24 pm - 7:01 amPDX-MIA
5h 37mnonstop
American Airlines Logo
7:40 pm - 11:07 pmMIA-PDX
6h 27mnonstop
$230American Airlines
Find Deal
Sat, May 24 - Fri, May 30
Spirit Airlines Logo
5:40 pm - 2:10 pmPDX-MIA
17h 30m2 stops
Spirit Airlines Logo
8:55 pm - 4:45 pmMIA-PDX
22h 50m1 stop
$241Spirit Airlines
Find Deal
Mon, May 19 - Wed, May 21
Delta Logo
12:08 pm - 12:37 amPDX-MIA
9h 29m1 stop
Delta Logo
6:15 pm - 12:10 amMIA-PDX
8h 55m1 stop
$249Delta
Find Deal
Tue, May 13 - Mon, May 19
Delta Logo
7:05 pm - 6:27 amPDX-MIA
8h 22m1 stop
Delta Logo
6:05 pm - 11:52 pmMIA-PDX
8h 47m1 stop
$274Delta
Find Deal
Sun, Aug 3 - Fri, Aug 15
American Airlines Logo
10:24 pm - 7:01 amPDX-MIA
5h 37mnonstop
American Airlines Logo
7:43 am - 5:04 pmMIA-PDX
12h 21m1 stop
$296American Airlines
Find Deal
Sat, May 17 - Wed, May 21
Alaska Airlines Logo
6:00 am - 5:01 pmPDX-MIA
8h 01m1 stop
Alaska Airlines Logo
6:21 pm - 11:44 pmMIA-PDX
8h 23m1 stop
$367Alaska Airlines
Find Deal
Sun, May 11 - Tue, May 20
Alaska Airlines Logo
5:30 pm - 5:21 pmPDX-MIA
20h 51m1 stop
Alaska Airlines Logo
6:21 pm - 6:20 amMIA-PDX
14h 59m2 stops
$387Alaska Airlines
Find Deal
Fri, May 30 - Mon, Jun 2
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 August, when tickets cost $342 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $541 and $509 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 Friday. 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. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$83
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 28% 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 evening, when round-trip flights cost $247 on average. Morning departures are around 63% more expensive than evening flights, 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 $656.

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
Alaska AirlinesOverall score based on 9968 reviews
8.2Boarding
7.1Food
7.9Comfort
7.1Entertainment
8.5Crew
Airline reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

8.0 ExcellentAnonymous, Apr 2025PDX - PHX
Read more Alaska Airlines reviews

OUr pilot was very good and also a good landing in a very gusting Phoenix. Most important.

It was alright other than the changes in the Alaska Lounge. That and the migraine I had were disappointing. Other then that everything went well.

It was a short flight so no refreshments or entertainment which was fine.

Flying in both directions across country the gate designated on my boarding pass was wrong. From w to e across the country the passenger next to me coughed the entire way.

Although both planes (flights) had mechanical issue delaying both of my flights, the crew members handled everything with ease. Both flights had the smoothest take off and landing. I opted to upgrade my seat to first class and really lucked out getting the seat at the very front of the plane. Awesome treat to myself. I really enjoyed my flight.

The staff from check-in counter to the flight crew were great. Flight was right on schedule. 10/10

Changed flight from San Fran to Seattle Then with a Delayed takeoff barely made my connection Waited over an hour for luggage 😜

It was good. There was a mistake made in Seattle. Somehow we were bumped out of our seats as if we weren't on the flight anymore. The woman at the gate caught it and announced our name to come up and she fixed it.

I wouldn’t fly with Alaska again if you paid me.

I appreciated Alaska Airlines very much, they are expanding traveling locations globally as they partnered with another company and am excited and looking forward to our next traveling adventure with this great Airline. Thank you kindly

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.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

My seat had no padding, it was literally plywood with a plastic cover. I could not change seats on my 10 hour flight. My excitement for this trip helped me deal with the pain.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

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

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!

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Perfect for the money paid. Flight from Indianapolis to Fort Lauderdale. Very courteous airport staff and crew. The boarding process went very smooth. Indianapolis was in the middle of several sever storms, delaying boarding and they found a window between the storms, asked everyone for a quick boarding and we departed before we would be held longer by the next storm front. A little rough air 20 min or so after take off, however I’ll take that to being grounded the whole night. Seats kind of small, kind of hard, but very doable for the 2.5 hrs flight. Snacks and drinks available for purchase. We didn’t, as it was a late night flight. One of the checked luggage came wet in Florida and clothes inside got wet from the water that infiltrated through the zipper, I’m assuming it was in the rain in Indianapolis, I cannot blame Spirit as I think the baggage handlers are hired by the airport. I’ll be more careful next time, as I have suitcases that are more water proof and maybe I should only purchase that kind.

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

The flight was on time. The seats are very narrow.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

This was my first experience with Spirit. The flight was originally delayed because of mechanical problems. There was a major storm moving through our area later in the day. Spirit kept changing the gate and taking the plane for other flights. They did this 6 times until we left 7 hours later, right at the worse time. I am sure it is because they originally delayed the flight through their fault. They would have had to pay for everybody's hotel and later flight. It was a money decision. The pilot did an exceptional job flying and landing the plane in horrific weather. It was one of the roughest and shakiest landings that I have ever done in my extensive flying experience. I just can never go through this discount BS again. Spirit gave us a $30 voucher each for next travel and a $12 meal voucher... but that's nothing compared to sitting in an airport for 7 hours.

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