$147 Find Cheap Flights from Portland to Florida Keys - Compare and Save

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 9/1. 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.
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1 adult, Economy, 0 bags

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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$328
Key West
Key West1 stop$275
Miami
Miami1 stop$328
Key West
Key West1 stop$275

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

Sat, Nov 7 - Wed, Nov 11
Multiple Airlines Logo
6:31 pm - 9:04 am
PWM
-
EYW
14h 33m
1 stop
Multiple Airlines Logo
10:04 am - 5:51 pm
EYW
-
PWM
7h 47m
1 stop
$275Multiple Airlines
Sun, Sep 6 - Fri, Sep 11
American Airlines Logo
6:00 am - 11:36 am
PWM
-
EYW
5h 36m
1 stop
American Airlines Logo
3:30 pm - 10:13 pm
EYW
-
PWM
6h 43m
1 stop
$301American Airlines
Tue, Sep 22 - Sat, Oct 3
American Airlines Logo
7:00 am - 1:11 pm
PWM
-
EYW
6h 11m
1 stop
American Airlines Logo
2:30 pm - 9:45 pm
EYW
-
PWM
7h 15m
1 stop
$301American Airlines
Sun, Sep 6 - Fri, Sep 11
Breeze Airways Logo
7:00 am - 11:27 am
PWM
-
EYW
28h 27m
2 stops
Breeze Airways Logo
10:59 am - 10:28 am
EYW
-
PWM
23h 29m
1 stop
$302Breeze Airways
Tue, Jan 12 - Wed, Jan 20
Delta Logo
6:00 am - 1:37 pm
PWM
-
EYW
7h 37m
1 stop
Delta Logo
7:00 am - 4:59 pm
EYW
-
PWM
9h 59m
2 stops
$335Delta
Wed, Jan 13 - Wed, Jan 20
Delta Logo
6:00 am - 1:37 pm
PWM
-
EYW
7h 37m
1 stop
Delta Logo
7:00 am - 4:59 pm
EYW
-
PWM
9h 59m
2 stops
$335Delta
Wed, Sep 9 - Tue, Sep 15
United Airlines Logo
6:06 am - 2:46 pm
PWM
-
MIA
8h 40m
1 stop
United Airlines Logo
12:17 pm - 11:32 pm
MIA
-
PWM
11h 15m
2 stops
$354United Airlines
Thu, Sep 3 - Wed, Sep 9
United Airlines Logo
5:15 am - 4:31 pm
PWM
-
MIA
11h 16m
2 stops
United Airlines Logo
11:26 am - 6:29 pm
MIA
-
PWM
7h 03m
1 stop
$354United Airlines
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
5:40 am - 1:35 pm
PWM
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MIA
7h 55m
1 stop
Southwest Logo
7:45 am - 9:05 pm
MIA
-
PWM
13h 20m
2 stops
$360Southwest
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
5:40 am - 3:00 pm
PWM
-
MIA
9h 20m
2 stops
Southwest Logo
7:45 am - 9:05 pm
MIA
-
PWM
13h 20m
2 stops
$365Southwest
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 $383, 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 January, when tickets cost $338 (return) on average. On the other hand, the most expensive months are July and February, when the average cost of round-trip tickets is $540 and $510 respectively.

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, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low season

July

Cheapest flight

$147
Best time to beat the crowds but there is an average 33% increase 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.

Reviews of the top 4 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 4222 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

6.0 GoodGordon, Jul 2026
SAN - MCO
Read more Southwest reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

It is usually very pleasant. Good service for the price, international flights are even better

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

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

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

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.

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!

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

Bad experience going to DFW with an IT outage then bad on the way back with a nearly 5 hour delay that’s started as maintenance then caused us to wait further due to weather - which would not have happened if we had left on time.

Quick flight. No time to stress over it. Over before it begins.

Very good, boarded and took off on time and landed early

Delayed boarding because a flight attendant couldn't find the gate...sat on the plane for over an hour at the gate because AA couldn't get one of the planes behind us to move

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

The departure and arrival was on time. The fact that I could load my boarding tickets on the American airlines app.

Horrible experience, delays after delays. A flight that should arrive 11:50pm just landed past 1 am, and another 30min waiting for the baggage to come out. Very disappointing.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports