$130 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 7/1. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$217
Key West
Key West1 stop$429
Miami
Miami1 stop$217
Key West
Key West1 stop$429

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

Thu, Aug 27 - Sat, Sep 5
Delta Logo
2:08 pm - 1:07 am
PDX
-
MIA
7h 59m
1 stop
Delta Logo
6:40 am - 1:38 pm
MIA
-
PDX
9h 58m
1 stop
$217Delta
Wed, Aug 26 - Sat, Sep 5
Delta Logo
12:35 am - 1:32 pm
PDX
-
MIA
9h 57m
1 stop
Delta Logo
6:40 am - 1:38 pm
MIA
-
PDX
9h 58m
1 stop
$222Delta
Fri, Oct 2 - Thu, Oct 8
Delta Logo
5:30 am - 5:09 pm
PDX
-
MIA
8h 39m
1 stop
Delta Logo
8:00 am - 4:13 pm
MIA
-
PDX
11h 13m
1 stop
$227Delta
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
11:30 pm - 2:25 pm
PDX
-
MIA
11h 55m
2 stops
Southwest Logo
4:00 pm - 11:35 pm
MIA
-
PDX
10h 35m
1 stop
$232Southwest
Tue, Sep 15 - Tue, Sep 22
Southwest Logo
11:30 pm - 1:35 pm
PDX
-
MIA
11h 05m
2 stops
Southwest Logo
2:25 pm - 9:55 pm
MIA
-
PDX
10h 30m
2 stops
$237Southwest
Tue, Nov 10 - Thu, Nov 19
Delta Logo
5:10 pm - 6:15 am
PDX
-
MIA
10h 05m
1 stop
Delta Logo
8:00 am - 4:13 pm
MIA
-
PDX
11h 13m
1 stop
$238Delta
Wed, Nov 11 - Tue, Nov 17
United Airlines Logo
10:00 am - 10:16 pm
PDX
-
MIA
9h 16m
1 stop
United Airlines Logo
6:20 am - 12:13 pm
MIA
-
PDX
8h 53m
1 stop
$239United Airlines
Mon, Jun 29 - Tue, Jul 7
Delta Logo
12:33 am - 1:35 pm
PDX
-
MIA
10h 02m
1 stop
Delta Logo
6:26 pm - 11:54 pm
MIA
-
PDX
8h 28m
1 stop
$243Delta
Wed, Oct 28 - Wed, Nov 4
United Airlines Logo
7:10 am - 6:05 pm
PDX
-
MIA
7h 55m
1 stop
United Airlines Logo
11:25 am - 8:33 pm
MIA
-
PDX
12h 08m
2 stops
$244United Airlines
Sat, Jul 4 - Fri, Jul 10
American Airlines Logo
5:07 am - 4:54 pm
PDX
-
EYW
8h 47m
1 stop
American Airlines Logo
4:41 pm - 11:55 pm
EYW
-
PDX
10h 14m
1 stop
$508American 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 $466 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 $645.

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 $415, 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 February, when tickets cost $92 (return) on average. On the other hand, the most expensive months are January and May, when the average cost of round-trip tickets is $837 and $199 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 Wednesday and more expensive on a Friday. On your return trip to Portland, you should consider flying back on a Tuesday, and avoid Saturdays 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 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$130
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 15% 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 12509 reviews
7.8Comfort
8.5Crew
7.0Food
7.0Entertainment
8.1Boarding
Airline reviews

Great trip. No complaints. Impressed with the crew’s response to various challenges pre-boarding.

10.0 ExcellentAnonymous, Jun 2026
PDX - OAK
Read more Alaska Airlines reviews

Great trip. No complaints. Impressed with the crew’s response to various challenges pre-boarding.

We were 35 minutes late because the caterer had not stocked the plane. Plane was fully loaded and ready to go 15 minutes before departure time. We sat there 35 minutes?

The seats are too small/crowded. It is frustrating to be forced to sit with someone who is overweight as they crown the other seat. Nothing against the person…just the airline companies who continue(over decades!)to reduce seat sizes. Americans are fat. Those of us who are not are tired of being compromised by the airline companies who don’t faces that fact and make adjustments. Maybe have “overweight seats”? Maybe give us a discount for being forced into an uncomfortable flight due to others overweightness? Please, make adjustments…be accountable. Thanks!

I flew standby with my two children and completely forgot it was Memorial Day weekend. We tried to fly from PDX to YVR. Unfortunately, after four attempts, we gave up and tried SEA instead after the holiday. The ground crew was very helpful, checking us in and accommodating us when we were finally able to get on a flight. The sad part was that they accidentally loaded one of my suitcases on the Vancouver flight without us during one of our attempts to get on a flight, even though it had a standby tag on it. I filed a report with baggage services, and thankfully, it was returned to PDX the following day. AS was in touch with us and updated us on the process of returning the luggage to the USA.

Internet was great. It was nice to watch a movie. The crew was very nice.

On this flight there wer only 25 people on board. So no one in 5 rows ahead of me and noone in 7 rows behind me. So very chill.

Considering my flight to Portland was in a broken chair that I had paid extra for, this one was great. So yeah, wonderful.

Some food or at least snacks need to be offered on long flights. I thought I had ordered food for my husband and I prior to the flight, but was told during the flight that I had not. Perhaps, if you must charge extra for food, let people order on board. We did get some food, which evidently others had decided they didn’t want onboard, but it wasn’t very good. We did like the adherence to takeoff and landing times, and the quick return of our luggage.

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

very nice blankets and comfortable seats. great service. Great flights.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

N Everything was perfect from boarding to assistance to baggage in Tampa

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

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

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

This planes staff was top tier. Everything went great and had a great flight home.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

The flight was delayed from take off because only one runway was operational in San Francisco.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports