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Cheap flights from Florida Keys to Boston from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida Keys to Boston departing on 3/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:50 pm - 10:35 pm
MIA
-
PWM
5h 45m
1 stop
Southwest Logo
2:50 pm - 11:00 pm
PWM
-
MIA
8h 10m
1 stop
$217Southwest
Wed, Apr 15 - Thu, Apr 23
Southwest Logo
7:00 am - 3:20 pm
MIA
-
PWM
8h 20m
2 stops
Southwest Logo
2:50 pm - 11:00 pm
PWM
-
MIA
8h 10m
1 stop
$222Southwest
Wed, Apr 15 - Thu, Apr 23
Delta Logo
7:40 am - 1:50 pm
MIA
-
PWM
6h 10m
1 stop
Delta Logo
6:25 am - 2:20 pm
PWM
-
MIA
7h 55m
1 stop
$234Delta
Tue, Mar 31 - Wed, Apr 8
Delta Logo
7:12 am - 1:58 pm
MIA
-
PWM
6h 46m
1 stop
Delta Logo
6:50 pm - 12:56 am
PWM
-
MIA
6h 06m
1 stop
$278Delta
Wed, Jun 3 - Tue, Jun 9
Southwest Logo
12:10 pm - 10:35 pm
MIA
-
PWM
10h 25m
2 stops
Southwest Logo
2:50 pm - 11:00 pm
PWM
-
MIA
8h 10m
1 stop
$293Southwest
Wed, May 13 - Mon, May 18
American Airlines Logo
5:18 pm - 10:40 pm
MIA
-
PWM
5h 22m
1 stop
American Airlines Logo
5:57 pm - 12:33 am
PWM
-
MIA
6h 36m
1 stop
$294American Airlines
Wed, Jul 22 - Mon, Aug 10
American Airlines Logo
4:02 pm - 11:27 pm
MIA
-
PWM
7h 25m
1 stop
American Airlines Logo
7:23 pm - 12:59 am
PWM
-
MIA
5h 36m
1 stop
$297American Airlines
Tue, Apr 14 - Thu, Apr 23
United Airlines Logo
12:30 pm - 9:51 pm
MIA
-
PWM
9h 21m
1 stop
United Airlines Logo
5:15 am - 3:04 pm
PWM
-
MIA
9h 49m
2 stops
$302United Airlines
Wed, Jun 3 - Tue, Jun 9
United Airlines Logo
12:30 pm - 11:51 pm
MIA
-
PWM
11h 21m
2 stops
United Airlines Logo
5:15 am - 4:16 pm
PWM
-
MIA
11h 01m
2 stops
$307United Airlines
Wed, Jun 3 - Tue, Jun 9
Multiple Airlines Logo
9:46 am - 9:07 am
EYW
-
PWM
23h 21m
1 stop
Multiple Airlines Logo
6:19 pm - 5:02 pm
PWM
-
EYW
22h 43m
2 stops
$698Multiple Airlines
Sun, Mar 15 - Thu, Mar 19

Delta flights from Florida Keys to Portland, Maine

Our best Delta deals on Florida Keys to Portland, Maine flight tickets
Delta
Apr 16
MIA7:40 amMiami
6h 31m
1 stop
PWM2:11 pmPortland
Apr 22
PWM2:51 pmPortland
8h 38m
1 stop
MIA11:29 pmMiami
$217
Delta
Mar 31
MIA7:40 amMiami
6h 10m
1 stop
PWM1:50 pmPortland
Apr 8
PWM6:25 amPortland
7h 55m
1 stop
MIA2:20 pmMiami
$234
Delta
Jun 3
MIA7:12 amMiami
6h 46m
1 stop
PWM1:58 pmPortland
Jun 9
PWM6:50 pmPortland
6h 06m
1 stop
MIA12:56 amMiami
$278

Southwest flights from Florida Keys to Portland, Maine

Our best Southwest deals on Florida Keys to Portland, Maine flight tickets
Southwest
Apr 15
MIA7:00 amMiami
8h 20m
2 stops
PWM3:20 pmPortland
Apr 23
PWM2:50 pmPortland
8h 10m
1 stop
MIA11:00 pmMiami
$222
Southwest
May 13
MIA12:10 pmMiami
10h 25m
2 stops
PWM10:35 pmPortland
May 18
PWM2:50 pmPortland
8h 10m
1 stop
MIA11:00 pmMiami
$293
Southwest
Apr 16
MIA6:20 amMiami
9h 55m
2 stops
PWM4:15 pmPortland
Apr 25
PWM5:40 amPortland
10h 25m
2 stops
MIA4:05 pmMiami
$298

momondo Fare Finder

 
Customize your flight search to find flights from Florida Keys to Portland, Maine that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 2, 2026.
Use the filters below to find and compare flights from Florida Keys to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 4/15

4:50 pm-10:35 pm

1 stop5h 45m

Portland

Thu 4/23

2:50 pm-11:00 pm

1 stop8h 10m

$217

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 4/15

7:00 am-3:20 pm

2 stops8h 20m

Portland

Thu 4/23

2:50 pm-11:00 pm

1 stop8h 10m

$222

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 3/31

7:40 am-1:50 pm

1 stop6h 10m

Portland

Wed 4/8

6:25 am-2:20 pm

1 stop7h 55m

$234

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 6/3

7:12 am-1:58 pm

1 stop6h 46m

Portland

Tue 6/9

6:50 pm-12:56 am

1 stop6h 06m

$278

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 5/13

12:10 pm-10:35 pm

2 stops10h 25m

Portland

Mon 5/18

2:50 pm-11:00 pm

1 stop8h 10m

$293

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 7/22

5:18 pm-10:40 pm

1 stop5h 22m

Portland

Mon 8/10

5:57 pm-12:33 am

1 stop6h 36m

$294

MiamiPortland

MIA - PWM

MIAPWM

Miami

Tue 4/14

4:02 pm-11:27 pm

1 stop7h 25m

Portland

Thu 4/23

7:23 pm-12:59 am

1 stop5h 36m

$297

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 6/3

12:30 pm-9:51 pm

1 stop9h 21m

Portland

Tue 6/9

5:15 am-3:04 pm

2 stops9h 49m

$302

MiamiPortland

MIA - PWM

MIAPWM

Miami

Wed 6/3

12:30 pm-11:51 pm

2 stops11h 21m

Portland

Tue 6/9

5:15 am-4:16 pm

2 stops11h 01m

$307

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sun 3/15

9:46 am-9:07 am

1 stop23h 21m

Portland

Thu 3/19

6:19 pm-5:02 pm

2 stops22h 43m

$698

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Boston from

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

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

What is the cheapest month to fly to Portland, Maine?

The cheapest month to fly to Portland, Maine from Florida Keys is in February. Flight prices, which tend to average around $277, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of February, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $287.

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

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

Cheap Florida Keys to Portland, Maine flight deals and tips

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

Fastest flight time

4h 45m

Direct flights

None
The fastest flight from Florida Keys to Portland, Maine takes 4h 45m
There are no direct flights from Florida Keys to Portland, Maine. There are no popular flight routes from Florida Keys to Portland, Maine.
Search flight deals

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

    Prices for flights from Florida Keys to Portland Airport were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Florida Keys to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The necessary travel and health documents for your Portland Airport 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 Florida Keys to Portland, Maine?

Best airlines flying from Florida Keys to Portland, Maine

Compare and see reviews for airlines that fly from Florida Keys to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $268Free CancellationRating
7.1
11,369 reviews
Search American Airlines flights
DeltaPriceFrom $274Free CancellationRating
7.9
8,237 reviews
Search Delta flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
Oxford
Georgetown
Falmouth
Tamworth

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Florida Keys to Portland for you.

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

Flights from Florida Keys to Portland with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Florida Keys to Portland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

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

An easier way to manage your Portland, Maine trip

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