EYW - BOS

$86 Find Cheap Flights from Key West to Boston

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 Boston departing on 9/16. 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 Boston

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

Cheap Flights from Key West to Boston (EYW-BOS)

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

Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
7:31 pm - 12:59 amEYW-BOS
5h 28m1 stop
American Airlines Logo
6:00 am - 1:52 pmBOS-EYW
7h 52m1 stop
$171American Airlines
Find Deal
Thu, Oct 2 - Wed, Oct 8
American Airlines Logo
7:31 pm - 12:59 amEYW-BOS
5h 28m1 stop
American Airlines Logo
12:52 pm - 7:22 pmBOS-EYW
6h 30m1 stop
$172American Airlines
Find Deal
Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
7:31 pm - 12:59 amEYW-BOS
5h 28m1 stop
American Airlines Logo
9:20 am - 5:16 pmBOS-EYW
7h 56m2 stops
$176American Airlines
Find Deal
Thu, Oct 2 - Wed, Oct 8
American Airlines Logo
2:55 pm - 10:50 pmEYW-BOS
7h 55m1 stop
American Airlines Logo
9:20 am - 5:16 pmBOS-EYW
7h 56m2 stops
$177American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
JetBlue Logo
1:00 pm - 4:32 pmEYW-BOS
3h 32mnonstop
JetBlue Logo
8:15 am - 11:53 amBOS-EYW
3h 38mnonstop
$297JetBlue
Find Deal
Mon, Oct 20 - Sat, Oct 25
 Logo
6:36 pm - 1:44 pmEYW-BOS
19h 08m2 stops
 Logo
6:11 am - 10:04 amBOS-EYW
27h 53m3 stops
Sun, Aug 31 - Thu, Sep 4
Allegiant Air Logo
4:36 pm - 8:10 amEYW-BOS
15h 34m1 stop
Allegiant Air Logo
10:54 am - 9:02 amBOS-EYW
46h 08m2 stops
$406Allegiant Air
Find Deal
Wed, Oct 29 - Sun, Nov 2
United Airlines Logo
3:00 pm - 11:42 pmEYW-BOS
8h 42m2 stops
United Airlines Logo
5:30 am - 2:04 pmBOS-EYW
32h 34m2 stops
$476United Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
3:00 pm - 11:42 pmEYW-BOS
8h 42m2 stops
United Airlines Logo
5:30 am - 2:04 pmBOS-EYW
32h 34m2 stops
$511United Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
JetBlue Logo
12:45 pm - 4:15 pmEYW-BOS
3h 30mnonstop
JetBlue Logo
8:00 am - 11:53 amBOS-EYW
3h 53mnonstop
$558JetBlue
Find Deal
Expert advice

Expert advice for your flight from Key West to Boston

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Basic Economy offers a budget-friendly option with carry-on only and late boarding.

JetBlue

JetBlue’s Blue Basic allows a carry-on and personal item, offering great value.


Enjoy free gate-to-gate Wi-Fi and live TV on JetBlue flights.

Read more about JetBlueby Harriet Baskas
Airports
EYW

Arrive two hours early at EYW due to potential security line congestion, especially during peak hours when multiple flights depart simultaneously.

Read more about EYWby Paul Rubio
BOS

Use the Silver Line from BOS for a free, convenient trip to South Station in central Boston, taking about 20-30 minutes.

Read more about BOSby Blane Bachelor
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines and JetBlue

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Paul Rubio

Paul Rubio

Expert on EYW

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more
Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Booking Insights

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

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

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

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

If your flying dates are flexible, you should consider flying to Boston on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Key West to Boston. For your return ticket, we recommend flying on a Saturday and avoiding Thursdays for the best deals.

What is the cheapest month to fly from Key West to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Key West to Boston, 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 Key West to Boston is September, where tickets cost $300 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $577 and $545 respectively.

Can I save money by flying with a layover from Key West to Boston?

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $347 on average.

Good to know

Low seasonFebruary
Cheapest flight$86
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 48% increase in price.
Flight from Key West to Boston

When to book flights from Key West to Boston

Are your dates flexible? Find out the best times to travel from Key West to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Key West to Boston

  • What is the cheapest flight from Key West to Boston?

    In the last 3 days, the lowest price for a flight from Key West to Boston was $86 for a one-way ticket and $171 for a round-trip.

  • Do I need a passport to fly between Key West and Boston?

    A passport is not required to fly from Key West to Boston.

  • Which airports will I be using when flying from Key West to Boston?

    On your way to Boston, you’ll fly out from Key West. You’ll be landing at Boston Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Key West to Boston?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Key West to Boston flight route.

  • Which aircraft models fly most regularly from Key West to Boston?

    The Airbus A319 is the aircraft model that flies most regularly on the Key West to Boston flight route.

  • Which airline alliances offer flights from Key West to Boston?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Key West and Boston, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Key West to Boston, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Key West to Boston are Delta and American Airlines. With an average price for the route of $357 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $340 and an overall rating of 7.2.

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

    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 Boston.

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

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

    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 Boston with an airline and back to Key West with another airline. Booking your flights between Key West and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Boston?

    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 Boston from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Key West to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Key West to Boston Logan Intl.
Find which airlines fly direct from Key West Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Key West to Boston Logan Intl

Monday

JetBlue, Qatar Airways, TAP AIR PORTUGAL

JetBlue, Qatar Airways, +1 more

Thursday

JetBlue, Qatar Airways, TAP AIR PORTUGAL

JetBlue, Qatar Airways, +1 more

Friday

JetBlue, Qatar Airways, TAP AIR PORTUGAL

JetBlue, Qatar Airways, +1 more

Saturday

JetBlue, Qatar Airways, TAP AIR PORTUGAL

JetBlue, Qatar Airways, +1 more

Sunday

JetBlue, Qatar Airways, TAP AIR PORTUGAL

JetBlue, Qatar Airways, +1 more

See more direct flights

Direct returns

Boston Logan Intl to Key West

Monday

JetBlue, TAP AIR PORTUGAL

JetBlue, TAP AIR PORTUGAL

Thursday

JetBlue

JetBlue

Friday

JetBlue, TAP AIR PORTUGAL

JetBlue, TAP AIR PORTUGAL

Saturday

JetBlue, TAP AIR PORTUGAL

JetBlue, TAP AIR PORTUGAL

Sunday

JetBlue, TAP AIR PORTUGAL

JetBlue, TAP AIR PORTUGAL

See more direct flights

Reviews of the top 3 airlines serving from Key West to Boston

 
See real verified KAYAK customer reviews for airlines flying from Key West to Boston. 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 Boston? 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 7981 reviews
7.9Comfort
7.9Entertainment
8.2Boarding
7.3Food
8.5Crew
Airline reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

2.0 MediocreRosa, Jul 2025TPA - JFK
Read more Delta reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

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.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

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

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