$86 Find Cheap Flights from Key West to Maine

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Maine departing on 9/30. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Maine

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Maine, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Maine, as well as popular online travel agencies
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Cheap Flights from Key West to Maine

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$269
Boston
Boston1 stop$171
Portland
Portland1 stop$269
Boston
Boston1 stop$171

Book Cheap Key West to Maine Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Maine 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 Key West to Maine

Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
6:17 pm - 11:44 pmEYW-BOS
5h 27m1 stop
American Airlines Logo
6:00 am - 12:58 pmBOS-EYW
6h 58m1 stop
$171American Airlines
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Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
11:25 am - 7:42 pmEYW-BOS
8h 17m2 stops
American Airlines Logo
7:00 am - 12:55 pmBOS-EYW
5h 55m1 stop
$176American Airlines
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Wed, Sep 17 - Wed, Sep 24
Delta Logo
6:10 pm - 12:11 amEYW-PWM
6h 01m1 stop
Delta Logo
1:35 pm - 8:07 pmPWM-EYW
6h 32m1 stop
$269Delta
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Wed, Sep 10 - Wed, Sep 17
Delta Logo
6:20 pm - 12:03 amEYW-PWM
5h 43m1 stop
Delta Logo
6:00 am - 5:15 pmPWM-EYW
11h 15m2 stops
$274Delta
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Wed, Aug 13 - Sun, Aug 17
United Airlines Logo
2:12 pm - 11:59 pmEYW-BOS
9h 47m2 stops
United Airlines Logo
6:05 am - 12:41 pmBOS-EYW
6h 36m1 stop
$322United Airlines
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Tue, Aug 12 - Tue, Aug 19
United Airlines Logo
2:22 pm - 11:59 pmEYW-PWM
9h 37m2 stops
United Airlines Logo
6:00 am - 2:25 pmPWM-EYW
8h 25m1 stop
$329United Airlines
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Fri, Sep 12 - Sun, Sep 14
Logo
12:09 pm - 11:13 amEYW-BOS
23h 04m2 stops
Logo
2:18 pm - 11:52 amBOS-EYW
21h 34m3 stops
$428
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Sun, Aug 10 - Thu, Aug 14
Logo
4:20 pm - 8:11 amEYW-BOS
15h 51m1 stop
Logo
4:12 pm - 4:41 pmBOS-EYW
24h 29m3 stops
$446
Find Deal
Wed, Sep 10 - Wed, Sep 17
Breeze Airways Logo
9:47 am - 1:51 pmEYW-PWM
52h 04m3 stops
Breeze Airways Logo
2:21 pm - 11:52 amPWM-EYW
45h 31m2 stops
$872Breeze Airways
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Wed, Sep 17 - Wed, Sep 24
Breeze Airways Logo
9:47 am - 1:51 pmEYW-PWM
52h 04m3 stops
Breeze Airways Logo
2:21 pm - 11:52 amPWM-EYW
45h 31m2 stops
$885Breeze Airways
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Booking Insights

KAYAK's insights & trends for Key West to Maine flights

Get data-powered insights and trends into flights from Key West to Maine to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Key West to Maine?

What’s the cheapest day of the week to fly from Key West to Maine?

The average price of all round-trip flights from Key West to Maine clicked on KAYAK for each day over the last 12 months.

When flying from Key West to Maine, you should consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Key West, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

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Good to know

Low seasonFebruary
Cheapest flight$86
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Key West to Boston

FAQs - booking Maine flights

  • How does KAYAK find such low prices on flights from Key West to Maine?

    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 Key West to Maine.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Maine?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Maine 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 Key West to Maine?

    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 Key West to Maine 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 Key West to Maine?

    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 Key West to Maine 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 Maine?

    The cheapest time of day to fly to Maine is generally in the evening, when round-trip flights cost $392 on average. Morning departures are around 21% more expensive than evening flights, on average. The most expensive time of day to fly to Maine is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $482.

Reviews of the top airline flying from Key West to Maine

 
See real verified KAYAK customer reviews for airlines flying from Key West to Maine. 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 Key West to Maine? 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.
7.2
American AirlinesOverall score based on 10000 reviews
7.5Boarding
6.5Food
6.9Entertainment
7.2Comfort
8.0Crew
Airline reviews

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

8.0 ExcellentKimber, Jul 2025JAX - DFW
Read more American Airlines reviews

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Crew professional. Easy bag drop off. On time. Good entertainment.

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

They have lost any customer service care and support. Terrible airline now and been for awhile.

The flight was delayed leaving Miami. When we arrived in Charlotte, we were unable to park at our scheduled gate. We had to wait another 30-45 minutes before we could park at a different gate. All in all, we were delayed by almost two hours arriving in Charlotte.

Everything you need to know for your flight from Key West to Maine

Information on your arrival and departure airports

Key West (EYW)

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