$125 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 1/15. 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 24% 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$231
Key West
Key West2 stops$334
Miami
Miami1 stop$231
Key West
Key West2 stops$334

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

Sun, Jan 4 - Thu, Jan 8
United Airlines Logo
6:27 pm - 5:53 am
PDX
-
MIA
8h 26m1 stop
United Airlines Logo
6:20 am - 12:18 pm
MIA
-
PDX
8h 58m1 stop
$231United Airlines
Sun, Jan 18 - Tue, Jan 20
Frontier Logo
11:49 am - 5:48 am
PDX
-
MIA
14h 59m1 stop
Frontier Logo
6:18 pm - 10:33 am
MIA
-
PDX
43h 15m2 stops
$232Frontier
Sun, Jan 4 - Sat, Jan 10
United Airlines Logo
6:27 pm - 5:53 am
PDX
-
MIA
8h 26m1 stop
United Airlines Logo
6:20 am - 12:18 pm
MIA
-
PDX
8h 58m1 stop
$233United Airlines
Mon, Feb 16 - Wed, Feb 25
Delta Logo
1:27 pm - 10:26 am
PDX
-
MIA
17h 59m2 stops
Delta Logo
6:43 am - 12:25 pm
MIA
-
PDX
8h 42m1 stop
$236Delta
Sun, Feb 15 - Wed, Feb 25
Delta Logo
6:25 am - 5:52 pm
PDX
-
MIA
8h 27m1 stop
Delta Logo
7:50 am - 8:55 pm
MIA
-
PDX
16h 05m2 stops
$237Delta
Wed, Jan 28 - Mon, Feb 2
United Airlines Logo
8:30 am - 9:54 pm
PDX
-
MIA
10h 24m2 stops
United Airlines Logo
6:20 am - 12:18 pm
MIA
-
PDX
8h 58m1 stop
$238United Airlines
Sat, Jan 10 - Sat, Jan 17
United Airlines Logo
7:51 pm - 10:54 am
PDX
-
MIA
12h 03m2 stops
United Airlines Logo
6:20 am - 12:18 pm
MIA
-
PDX
8h 58m1 stop
$239United Airlines
Sat, Feb 28 - Mon, Mar 9
Alaska Airlines Logo
7:05 am - 4:59 pm
PDX
-
MIA
30h 54m1 stop
Alaska Airlines Logo
5:59 pm - 11:44 pm
MIA
-
PDX
8h 45m1 stop
$246Alaska Airlines
Thu, Jan 22 - Sat, Jan 31
American Airlines Logo
6:00 am - 9:47 pm
PDX
-
EYW
12h 47m2 stops
American Airlines Logo
4:37 pm - 11:46 pm
EYW
-
PDX
10h 09m1 stop
$334American Airlines
Thu, Jan 22 - Sat, Jan 31
American Airlines Logo
10:15 pm - 1:03 pm
PDX
-
EYW
11h 48m2 stops
American Airlines Logo
6:06 am - 5:52 pm
EYW
-
PDX
14h 46m2 stops
$339American 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.

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 $361, 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 $590 and $457 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 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 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$125
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 17% 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 70% 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 $654.

Top tips for finding cheap flights to Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Portland to the following destinations at these prices or less: Miami $181 one-way - $334 round-trip

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.
8.0
Alaska AirlinesOverall score based on 11448 reviews
7.0Entertainment
7.1Food
8.1Boarding
8.5Crew
7.8Comfort
Airline reviews

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

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

Flight was delayed but still made it to Phoenix on time. Boarding went quickly, the flight was smooth.

The food selections were not good, and entertainment was non existent.

I would have liked if the flight existed. To be fair the federal government canceled it. But, since it WAS canceled, I would have liked it if Alaska Airlines had moved a finger to assist me rather then abandoning me with my luggage, unable to check it, for 14 hours in Portland. So federal regulations forbid them from storing my bag? Then at least help me find storage or SOMETHING.

It was all good, no delays which was a worry. All great

It was a pleasant experience. Considering we paid over $3000 for first class there really wasn’t anything special about first class. All the seats looked the same and everyone got the same great customer service. The only thing that was different between first class and couch was the drinks and the meal. We wouldn’t waste that much $ on first class on that plane again.

This was more with the third party booking through Kayak but my KTN for Pre-TSA, even though I entered it, wasn't assigned to my ticket when I got to the airport. I had to go through regular security. Also the Alaska app had trouble loading my ticket in the first place and I had to ask for it to be printed. Alaska Airlines was great but wanted you to know about this hiccup in the ticketing interface.

Process of checking bag, boarding, etc. was all very quick, easy, and streamlined. Only problem I had was the seating: very cramped and uncomfortable, but I suppose that’s the perils of coach. Thankfully it wasn’t a super long flight so it didn’t ruin the experience overall.

The boarding was confusing because the PA system at PDX was so quiet you couldn’t hear anything being said . The seats were uncomfortable. The food was pretty bad and I normally don’t mind airplane food. The flight attendants were not friendly. I learned upon check in that Hawaiian airlines had reassigned our seats of the second leg of the trip. I had confirmed and paid for special seats but they put me and my companion on standard seats in different rows. Hawaiian also did the same on my return flight after the flight times had changed. I happened to go online to check my reservation and saw the flight had changed. I gad received no notice. I saw that my confirmed seats that I had paid extra were gone. After much back and forth with the airlines they refused to correct their error. I showed them confirmation documents of my seat reservation and receipt of payment but they refused to correct the seat change or reimburse me. I had to pay $200 again to reserve the original seats. Shameful and manipulative. They basically held me hostage. If I wanted to be in that flight I had to pay up.

When I bought my tickets I up great my seats for extra $104 each seats 8A and 8B in the way back from Portland to Palm Springs they gave me the seats 15. I thought it was for round trip same seats . So I was very disappointed ☹️

One disappointment. There was a gate change from B8 to B10, they had announced it maybe 20 minutes before the boarding time, possibly less. I didn’t hear the announcement as I was listening to music on my head phones at B8. At the boarding time, I got up and asked the gal at the B8 boarding desk, why the destination sign had not changed and if the flight was delayed as there was no plane behind her through the window, she said that perhaps the flight was delayed and the screen will probably update in -5 minutes ( she apparently didn’t know the boarding gate was changed ( 2 down from our location) I put my headphones on and went back to sit down . Just before the B10 door closed, I got a phone call asking me if I was still taking the flight, I said. “Yes” but I was at the gate stated on my ticket B8, then I was informed of the gate change, I got up and ran to the gate, and down the hallway to the jet ramp. I was the last to board!! Very frustrating . I was shocked that I got no emails or text messages from Alaska informing me of a last minute change!!

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

Unfortunately, I was put into the middle seat in the first row of premium seating. Sounds nice right? No! that is the worst seat in the plane. I wish I was in economy rather than be in that seat! There is no seat back pocket, no tray table, no charger. Nothing! so unless you're row mates are willing to let you share their basic amenities any flyer should have, you are stuck. It was the worst experience ever! And the flight attendant forgot to take my drink order. I felt like the forgotten flyer.

Delayed and cancelled flights were hard and very stressful, both ways!

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I had to cancel the flight because with a 3 hour delay for 'unexpected maintenance' in getting to LAX, I couldn't connect to an overseas flight that I had booked on Scandinavian Air.

The flight was CANCELED!!! Can’t get much more “poor” than that. I had to switch to American Airlines, add another layover and got home in Honolulu 4 hours later than I was supposed to be home. One bright spot was Josh with Alaska Airlines at SFO. He got me on a United Flight that got me home a few hours before I would have. Without him I would have gotten home almost 7 hours after my originally scheduled flight.

Canceled my flight within 24 hours, causing me arriving home midnight. Will never book Hawaiian airlines anymore

I like Hawaiian, it was great that they had good internet connection across the Pacific Ocean, thanks to Star Link satellites. The seating was comfortable, ( I was in economy ). Maybe I missed it, but I only got offered a beverage once. It was a nonstop flight KOA to SMF. I would take it again next time I go that way.

I always love flying Hawaii and I have nothing to add

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Always wish for more healthy, gluten free options. We have to bring our own.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports