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Find cheap flights from Portland to Florida Keys from $95

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 6/18. 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
0 bags
Wed 6/12
Wed 6/19

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Best Florida Keys Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Miami
Miami1 stop$155
Key West
Key West1 stop$197

Good to know

Low season

July

High season

February

Cheapest flight

$95
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 8% 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 to Florida Keys from Portland 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 to Florida Keys with an airline and back to Portland 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 to Florida Keys from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Portland to Florida Keys

 
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
DeltaOverall score based on 10736 reviews
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
Airline reviews

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

10.0 ExcellentDonnel, Apr 2024ATL - EYW
Read more about Delta reviews

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

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

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

Did not wait long for wheelchair and attendant to arrive after checking in. Wheeled down to plane Was greeted with a smile when entering the plane Choice of snacks was very limited to 2 items. Seats are uncomfortable. My butt was sore after the 1st hour of flying. Needs better cushioning at seats.

Did not wait long for wheelchair and attendant to arrive after checking in. Wheeled down to plane Was greeted with a smile when entering the plane Choice of snacks was very limited to 2 items.

One hour delayed departure resulted in problems with planned ground transportation at my destination.

No WiFi No TV Bag of chips I guess it could be worse.

I really liked the way snacks and drinks were available throughout the flight!!! The flight attendants were also all fantastic!

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Check in etc was very good. As for on the plane, it was like flying in a freezer. It was so cold, i have flown for years and never been so cold on a plane. Staff on board said its always cold when flying which is a load of rubbish. They wouldnt put any heating on and now i have the flu because of this .

I’ve had a couple flights this week on United that were delayed by an hour or more

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

It was a good flight. Of course it was full, but it went well.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

We are gluten free, there were not any available complimentary gluten free options.

Flight delayed 3 times. We were directed to go to a gate across from our gate. The plane wasn't there yet so we had to wait for it to arrive, then deplane everyone and then wait again for the plane to be cleaned. After 45 minuites we were allowed on the plane. The first plane had mechanical issues. The 2nd plane must have had bathroom issues because we did not have any food service whatsoever. No snack or beverage. That made for a long time not to have anything considering that we had just made it to the original gate and we had no time to stop to get food or a drink. Then we didn't want to leave the gate to get food because we wouldn't know how much longer the delay would be. Then the next gate change. Had we been told that the total time would have been aprox 45 min later we would have left to get food and a beverage. We had to wait again for the okay to the pilot to take off so we were on the runway for another 20 min. Overall, we were delayed over 2 hours which felt like 4 hours.

Lots of weather delays that were poorly communicated and managed. I get there are weather delays but they didn’t make it clear what was happening or comfortable on the plane

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

Horrible. Flight was delayed and very bumpy. I was super unhappy

Book cheap flights from Portland to Florida Keys

Recent round-trip flight deals

5/30Thu
1 stopFrontier
9h 04mPWM-MIA
6/8Sat
1 stopFrontier
6h 03mMIA-PWM
$155
5/30Thu
1 stopFrontier
9h 04mPWM-MIA
6/10Mon
1 stopFrontier
21h 53mMIA-PWM
$183
8/31Sat
1 stopAmerican Airlines
6h 20mPWM-EYW
9/4Wed
1 stopAmerican Airlines
7h 19mEYW-PWM
$197
9/17Tue
1 stopAmerican Airlines
6h 32mPWM-MIA
9/27Fri
1 stopAmerican Airlines
5h 27mMIA-PWM
$202
8/31Sat
1 stopAmerican Airlines
8h 21mPWM-EYW
9/4Wed
2 stopsAmerican Airlines
10h 41mEYW-PWM
$202
6/2Sun
1 stopDelta
6h 08mPWM-MIA
6/13Thu
1 stopDelta
9h 09mMIA-PWM
$216
5/29Wed
1 stopDelta
6h 08mPWM-MIA
6/11Tue
1 stopDelta
9h 09mMIA-PWM
$238
9/19Thu
1 stopUnited Airlines
6h 18mPWM-MIA
9/29Sun
1 stopUnited Airlines
8h 23mMIA-PWM
$362
5/28Tue
1 stopUnited Airlines
6h 40mPWM-MIA
5/30Thu
2 stopsUnited Airlines
17h 28mMIA-PWM
$417
8/5Mon
1 stopJetBlue
7h 59mPWM-MIA
8/10Sat
1 stopJetBlue
8h 06mMIA-PWM
$450

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Recent one-way flight deals

6/18Tue
1 stopFrontier
14h 17mPWM-MIA
$95
7/2Tue
1 stopAmerican Airlines
7h 46mPWM-MIA
$102
6/15Sat
1 stopDelta
8h 16mPWM-MIA
$108
6/13Thu
1 stopDelta
8h 16mPWM-MIA
$130
6/19Wed
1 stopJetBlue
8h 13mPWM-MIA
$159
7/16Tue
1 stopAmerican Airlines
5h 53mPWM-EYW
$162
6/16Sun
1 stopAmerican Airlines
6h 25mPWM-MIA
$168
11/9Sat
2 stopsDelta
8h 08mPWM-EYW
$168
11/9Sat
3 stopsUnited Airlines
33h 55mPWM-EYW
$260
7/2Tue
2 stopsUnited Airlines
25h 08mPWM-MIA
$323

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Last minute flights from Portland to Florida Keys

Last minute flight, train and bus deals

5/18Sat
multi-stopAmerican Airlines
6h 37mPWM-MIA
5/21Tue
multi-stopAmerican Airlines
5h 44mMIA-PWM
$657
5/18Sat
multi-stopAmerican Airlines
7h 02mPWM-MIA
5/21Tue
multi-stopAmerican Airlines
5h 44mMIA-PWM
$670
5/18Sat
multi-stopAmerican Airlines
9h 04mPWM-MIA
5/21Tue
multi-stopAmerican Airlines
10h 07mMIA-PWM
$687
5/15Wed
multi-stopAmerican Airlines
7h 22mPWM-MIA
5/19Sun
multi-stopAmerican Airlines
8h 19mMIA-PWM
$720
5/16Thu
multi-stopAmerican Airlines
7h 24mPWM-MIA
5/19Sun
multi-stopAmerican Airlines
8h 19mMIA-PWM
$721
5/17Fri
multi-stopAmerican Airlines
7h 24mPWM-MIA
5/20Mon
multi-stopAmerican Airlines
7h 11mMIA-PWM
$733
5/15Wed
multi-stopAmerican Airlines
9h 04mPWM-MIA
5/19Sun
multi-stopAmerican Airlines
8h 19mMIA-PWM
$743
5/16Thu
multi-stopAmerican Airlines
10h 10mPWM-MIA
5/19Sun
multi-stopAmerican Airlines
8h 19mMIA-PWM
$803
5/17Fri
multi-stopAmerican Airlines
9h 04mPWM-MIA
5/20Mon
multi-stopAmerican Airlines
7h 11mMIA-PWM
$853
5/16Thu
multi-stopAmerican Airlines
10h 10mPWM-MIA
5/19Sun
multi-stopAmerican Airlines
7h 22mMIA-PWM
$977

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Portland - Florida Keys Flights

Departure:

Portland (PWM)United States

Return flight deals:

Florida Keys - Portland

Cabin classes:

$701
$895
$268
$58