What is the cheapest airline that flies from Portland to Florida Keys?

United Airlines, Delta, and Breeze Airways are the most popular carriers operating from Portland to Florida Keys

What airlines fly to Florida Keys?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Florida Keys from Portland, Maine according to our data. American Airlines is the first choice among our users, with 57% of people opting to fly with this airline when traveling to Florida Keys. Keep in mind that there are 4 different airlines that fly to Florida Keys on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Portland Airport to Florida Keys?

Prices for flights from Portland Airport to Florida Keys are updated daily.

How many operators does momondo search for flights from Portland Airport to Florida Keys?

There are 4 operators available for flights from Portland Airport to Florida Keys as of August 2026.

How old do you have to be to fly from Portland Airport to Florida Keys?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Florida Keys.

What documentation or ID do you need to fly to Florida Keys?

The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$131 Cheap Flights from Portland, Maine to Florida Keys in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Florida Keys

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:30 am - 11:33 amPWM Portland-MIA Miami

6h 03m1 stop Washington, D.C. Dulles Intl

5:28 pm - 11:21 pmMIA Miami-PWM Portland

5h 53m1 stop Newark

$261United Airlines

Tue, Oct 27 - Tue, Oct 27

6:00 am - 12:08 pmPWM Portland-MIA Miami

6h 08m1 stop Washington, D.C. Reagan-National

2:17 pm - 9:36 pmMIA Miami-PWM Portland

7h 19m1 stop Philadelphia

$261American Airlines

Wed, Oct 21 - Tue, Oct 27

6:00 am - 12:21 pmPWM Portland-MIA Miami

6h 21m1 stop New York LaGuardia

5:59 pm - 11:49 pmMIA Miami-PWM Portland

5h 50m1 stop New York John F Kennedy Intl

$261Delta

Sat, Feb 6 - Sat, Feb 13

4:27 pm - 10:38 pmPWM Portland-MIA Miami

6h 11m1 stop New York LaGuardia

7:54 am - 3:43 pmMIA Miami-PWM Portland

7h 49m1 stop Washington, D.C. Reagan-National

$261American Airlines

Sat, Oct 17 - Sat, Oct 24

6:00 am - 5:19 pmPWM Portland-MIA Miami

11h 19m2 stops Newark Chicago O'Hare Intl

5:20 pm - 10:57 pmMIA Miami-PWM Portland

5h 37m1 stop Newark

$266United Airlines

Sat, Feb 6 - Sat, Feb 13

6:31 pm - 9:04 amPWM Portland-EYW Key West

14h 33m1 stop Tampa

10:04 am - 5:51 pmEYW Key West-PWM Portland

7h 47m1 stop Tampa

$275Multiple Airlines

Sat, Nov 14 - Wed, Nov 18

6:31 pm - 9:04 amPWM Portland-EYW Key West

14h 33m1 stop Tampa

10:04 am - 5:51 pmEYW Key West-PWM Portland

7h 47m1 stop Tampa

$276Multiple Airlines

Sat, Nov 14 - Wed, Nov 18

6:00 am - 12:21 pmPWM Portland-MIA Miami

6h 21m1 stop New York LaGuardia

8:45 am - 4:59 pmMIA Miami-PWM Portland

8h 14m1 stop New York LaGuardia

$279Delta

Tue, Jan 5 - Thu, Jan 7

11:35 am - 9:35 pmPWM Portland-MIA Miami

10h 00m2 stops Nashville Intl Baltimore/Washington

6:05 am - 1:05 pmMIA Miami-PWM Portland

7h 00m1 stop Baltimore/Washington

$289Southwest

Tue, Oct 27 - Mon, Nov 2

3:25 pm - 10:35 pmPWM Portland-MIA Miami

7h 10m1 stop Baltimore/Washington

6:45 am - 12:15 pmMIA Miami-PWM Portland

5h 30m1 stop Baltimore/Washington

$337Southwest

Fri, Oct 23 - Sat, Oct 31

Cheap last minute flights

Enter your travel dates to find the best prices.

7:00 am - 12:34 pmPWM Portland-EYW Key West

29h 34m2 stops Cincinnati Cinci./N. Kentucky Tampa

11:46 am - 5:58 pmEYW Key West-PWM Portland

6h 12m1 stop Tampa

$437Multiple Airlines

Mon, Aug 17 - Wed, Aug 26

7:00 am - 12:34 pmPWM Portland-EYW Key West

29h 34m2 stops Cincinnati Cinci./N. Kentucky Tampa

11:07 am - 4:16 pmEYW Key West-PWM Portland

29h 09m1 stop Raleigh-Durham

$459Multiple Airlines

Mon, Aug 17 - Fri, Aug 21

7:28 am - 1:45 pmPWM Portland-EYW Key West

6h 17m1 stop Philadelphia

2:31 pm - 9:21 pmEYW Key West-PWM Portland

6h 50m1 stop Philadelphia

$491American Airlines

Tue, Aug 18 - Wed, Aug 26

7:28 am - 1:45 pmPWM Portland-EYW Key West

6h 17m1 stop Philadelphia

2:31 pm - 9:21 pmEYW Key West-PWM Portland

6h 50m1 stop Philadelphia

$491American Airlines

Tue, Aug 18 - Tue, Aug 25

6:05 am - 1:00 pmPWM Portland-EYW Key West

6h 55m1 stop Atlanta Hartsfield-Jackson

4:00 pm - 9:31 pmEYW Key West-PWM Portland

5h 31m1 stop Atlanta Hartsfield-Jackson

$530Delta

Mon, Aug 17 - Sat, Aug 22

6:05 am - 1:00 pmPWM Portland-EYW Key West

6h 55m1 stop Atlanta Hartsfield-Jackson

7:40 am - 1:07 pmEYW Key West-PWM Portland

5h 27m1 stop Atlanta Hartsfield-Jackson

$530Delta

Mon, Aug 17 - Wed, Aug 26

5:55 am - 3:20 pmPWM Portland-MIA Miami

9h 25m2 stops Baltimore/Washington Dallas Love Field

7:30 am - 12:25 pmMIA Miami-PWM Portland

4h 55m1 stop Baltimore/Washington

$621Southwest

Fri, Aug 14 - Tue, Aug 18

5:55 am - 3:20 pmPWM Portland-MIA Miami

9h 25m2 stops Baltimore/Washington Dallas Love Field

9:15 am - 5:15 pmMIA Miami-PWM Portland

8h 00m2 stops Nashville Intl Baltimore/Washington

$626Southwest

Fri, Aug 14 - Tue, Aug 18

6:03 am - 2:54 pmPWM Portland-MIA Miami

8h 51m1 stop Chicago O'Hare Intl

1:44 pm - 11:32 pmMIA Miami-PWM Portland

9h 48m2 stops Washington, D.C. Dulles Intl Newark

$666United Airlines

Mon, Aug 17 - Wed, Aug 26

5:15 am - 2:46 pmPWM Portland-MIA Miami

9h 31m2 stops Washington, D.C. Dulles Intl Newark

5:37 pm - 11:32 pmMIA Miami-PWM Portland

5h 55m1 stop Newark

$670United Airlines

Fri, Aug 14 - Mon, Aug 17

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American Airlines flights from Portland, Maine to Florida Keys

Our best American Airlines deals on Portland, Maine to Florida Keys flight tickets

American Airlines

Oct 21

PWM6:00 amPortland

6h 08m

1 stop

MIA12:08 pmMiami

Oct 27

MIA2:17 pmMiami

7h 19m

1 stop

PWM9:36 pmPortland

$261

American Airlines

Oct 22

PWM6:00 amPortland

6h 08m

1 stop

MIA12:08 pmMiami

Oct 27

MIA3:20 pmMiami

6h 16m

1 stop

PWM9:36 pmPortland

$279

American Airlines

Oct 16

PWM5:37 pmPortland

5h 59m

1 stop

MIA11:36 pmMiami

Oct 24

MIA6:12 pmMiami

5h 24m

1 stop

PWM11:36 pmPortland

$297

Delta flights from Portland, Maine to Florida Keys

Our best Delta deals on Portland, Maine to Florida Keys flight tickets

Delta

Sep 5

PWM12:10 pmPortland

6h 43m

1 stop

MIA6:53 pmMiami

Sep 12

MIA1:55 pmMiami

7h 20m

1 stop

PWM9:15 pmPortland

$295

Delta

Nov 14

PWM2:15 pmPortland

5h 47m

1 stop

EYW8:02 pmKey West

Nov 18

EYW7:35 amKey West

8h 23m

2 stops

PWM3:58 pmPortland

$306

Delta

Jan 12

PWM6:00 amPortland

11h 11m

2 stops

EYW5:11 pmKey West

Jan 20

EYW7:00 amKey West

9h 59m

2 stops

PWM4:59 pmPortland

$311

momondo Fare Finder

Use the filters below to find and compare flights from Portland, Maine to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Tue 10/27

5:30 am-11:33 am

1 stop6h 03m

Miami

Tue 10/27

5:28 pm-11:21 pm

1 stop5h 53m

$261

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Wed 10/21

6:00 am-12:08 pm

1 stop6h 08m

Miami

Tue 10/27

2:17 pm-9:36 pm

1 stop7h 19m

$261

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Sat 2/6

6:00 am-12:21 pm

1 stop6h 21m

Miami

Sat 2/13

5:59 pm-11:49 pm

1 stop5h 50m

$261

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Sat 10/17

4:27 pm-10:38 pm

1 stop6h 11m

Miami

Sat 10/24

7:54 am-3:43 pm

1 stop7h 49m

$261

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Sat 2/6

6:00 am-5:19 pm

2 stops11h 19m

Miami

Sat 2/13

5:20 pm-10:57 pm

1 stop5h 37m

$266

PortlandKey West

PWM Portland - EYW Key West

PWMEYW

Portland

Sat 11/14

6:31 pm-9:04 am

1 stop14h 33m

Key West

Wed 11/18

10:04 am-5:51 pm

1 stop7h 47m

$275

PortlandKey West

PWM Portland - EYW Key West

PWMEYW

Portland

Sat 11/14

6:31 pm-9:04 am

1 stop14h 33m

Key West

Wed 11/18

10:04 am-5:51 pm

1 stop7h 47m

$276

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Tue 1/5

6:00 am-12:21 pm

1 stop6h 21m

Miami

Thu 1/7

8:45 am-4:59 pm

1 stop8h 14m

$279

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Tue 10/27

11:35 am-9:35 pm

2 stops10h 00m

Miami

Mon 11/2

6:05 am-1:05 pm

1 stop7h 00m

$289

PortlandMiami

PWM Portland - MIA Miami

PWMMIA

Portland

Fri 10/23

3:25 pm-10:35 pm

1 stop7h 10m

Miami

Sat 10/31

6:45 am-12:15 pm

1 stop5h 30m

$337

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland, Maine to Florida Keys

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Florida Keys?

The month of September is another great option to travel to Florida Keys, with average flight prices from Portland, Maine averaging around $349.

How far in advance should I book a flight from Portland, Maine to Florida Keys?

You are more likely to see cheaper flights to Florida Keys from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $412 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Portland, Maine for as low as $339 on momondo.

Can stopping save me money on Portland, Maine to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Portland, Maine to Florida Keys.

Cheap Portland, Maine to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Florida Keys

Fastest flight time	5h 31m
Direct flights	None

The fastest flight from Portland, Maine to Florida Keys takes 5h 31m

There are no direct flights from Portland, Maine to Florida Keys. There are no popular flight routes from Portland, Maine to Florida Keys.

Search flight deals

Frequently asked questions about flying from Portland, Maine to Florida Keys

When did momondo last update prices for flights from Portland Airport to Florida Keys?
Prices for flights from Portland Airport to Florida Keys are updated daily.
How many operators does momondo search for flights from Portland Airport to Florida Keys?
There are 4 operators available for flights from Portland Airport to Florida Keys as of August 2026.
How old do you have to be to fly from Portland Airport to Florida Keys?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Florida Keys.
What documentation or ID do you need to fly to Florida Keys?
The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland, Maine to Florida Keys?
Based on momondo bookings for flights between Portland, Maine and Florida Keys, the leading plane model is Boeing 737 MAX 8, making up 15.38% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 12.68%, Airbus A220-300 with 10.00%, and Canadair (Bombardier) Regional Jet 900 with 8.97%.

Best airlines flying from Portland, Maine to Florida Keys

Compare and see reviews for airlines that fly from Portland, Maine to Florida Keys with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $256	Free Cancellation	Rating 7.4 10,111 reviews	Search United Airlines flights
Delta	PriceFrom $256	Free Cancellation	Rating 7.8 8,502 reviews	Search Delta flights
American Airlines	PriceFrom $290	Free Cancellation	Rating 7.1 11,923 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Florida Keys?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Florida Keys. momondo saves you time and could save you money on your trip.

Can I find flights from Portland to Florida Keys with flexible booking policies on momondo?

momondo does allow users to show only those flights to Florida Keys from Portland which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Portland to Florida Keys?

momondo provides multiple filters to help you find the best flight to Florida Keys from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Portland to Florida Keys right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Florida Keys, momondo offers a useful price alert feature which will track prices for flights to Florida Keys from Portland and alert you when they change.