EYW - BOS

$92 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 1/29. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$166
Overall average: $430
Spirit Airlines
Thu 1/29Mon 2/2
EYW - BOS • 1 stop
Cheapest non-stop
$218
JetBlue
Sat 1/17Wed 1/21
EYW - BOS • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue’s Blue Basic offers carry-on and live TV.
Arrive two hours early at EYW for security lines.
Expert advice
Expert advice
Expert advice
Expert advice
When to travel
November
Cheapest • 24% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Expert advice
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

Thu, Jan 29 - Mon, Feb 2
Spirit Airlines Logo
12:51 pm - 11:57 pm
EYW
-
BOS
11h 06m1 stop
Spirit Airlines Logo
5:34 am - 1:30 pm
BOS
-
EYW
7h 56m1 stop
$166Spirit Airlines
Thu, Jan 29 - Mon, Feb 2
United Airlines Logo
6:05 pm - 11:49 pm
EYW
-
BOS
5h 44m1 stop
United Airlines Logo
9:30 am - 4:22 pm
BOS
-
EYW
6h 52m1 stop
$197United Airlines
Thu, Jan 29 - Mon, Feb 2
United Airlines Logo
2:25 pm - 11:49 pm
EYW
-
BOS
9h 24m2 stops
United Airlines Logo
6:00 am - 1:03 pm
BOS
-
EYW
7h 03m1 stop
$202United Airlines
Thu, Jan 15 - Sat, Jan 17
Multiple Airlines Logo
10:06 am - 11:19 pm
EYW
-
BOS
13h 13m1 stop
Multiple Airlines Logo
3:43 pm - 9:26 am
BOS
-
EYW
17h 43m1 stop
$206Multiple Airlines
Thu, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
10:06 am - 11:19 pm
EYW
-
BOS
13h 13m1 stop
Multiple Airlines Logo
5:34 am - 1:30 pm
BOS
-
EYW
7h 56m1 stop
$208Multiple Airlines
Thu, Jan 29 - Mon, Feb 2
Multiple Airlines Logo
10:06 am - 11:19 pm
EYW
-
BOS
13h 13m1 stop
Multiple Airlines Logo
5:34 am - 1:30 pm
BOS
-
EYW
7h 56m1 stop
$211Multiple Airlines
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
6:05 pm - 11:49 pm
EYW
-
BOS
5h 44m1 stop
United Airlines Logo
9:30 am - 4:22 pm
BOS
-
EYW
6h 52m1 stop
$217United Airlines
Sat, Jan 17 - Wed, Jan 21
JetBlue Logo
1:00 pm - 4:36 pm
EYW
-
BOS
3h 36mnonstop
JetBlue Logo
8:09 am - 12:05 pm
BOS
-
EYW
3h 56mnonstop
$218JetBlue
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
2:25 pm - 11:49 pm
EYW
-
BOS
9h 24m2 stops
United Airlines Logo
9:30 am - 4:22 pm
BOS
-
EYW
6h 52m1 stop
$222United Airlines
Thu, Jan 22 - Mon, Jan 26
JetBlue Logo
1:00 pm - 4:36 pm
EYW
-
BOS
3h 36mnonstop
JetBlue Logo
8:09 am - 12:05 pm
BOS
-
EYW
3h 56mnonstop
$223JetBlue
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 Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Key West to Boston. For your return ticket, we recommend flying on a Sunday 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 November, where tickets cost $301 (return) on average. On the other hand, the most expensive months are September and April, where the average cost of round-trip tickets is $609 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 $402 on average.

Expert advice

Expert advice for your flight from Key West to Boston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

Airports
EYW

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

BOS

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

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

Good to know

Low seasonSeptember
Cheapest flight$92
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly and prices are also 13% lower on average.
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 $92 for a one-way ticket and $197 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?

    JetBlue, and American Airlines 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 A220-300 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 is the only airline alliance operating flights between Key West and Boston.

  • On which days can I fly direct from Key West to Boston?

    There are nonstop flights from Key West to Boston on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Key West to Boston are American Airlines and JetBlue. With an average price for the route of $346 and an overall rating of 7.2, American Airlines is the most popular choice. JetBlue is also a great choice for the route, with an average price of $447 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.

KAYAK’s top tips for finding a cheap flight from Key West to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $268 or less one-way.

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

JetBlue

Tuesday

JetBlue

JetBlue

Wednesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

American Airlines, JetBlue

American Airlines, JetBlue

Saturday

American Airlines, JetBlue

American Airlines, JetBlue

Sunday

American Airlines, JetBlue

American Airlines, JetBlue

See more direct flights

Direct returns

Boston Logan Intl to Key West

Monday

JetBlue

JetBlue

Tuesday

JetBlue

JetBlue

Wednesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

American Airlines, JetBlue

American Airlines, JetBlue

Saturday

American Airlines, JetBlue

American Airlines, JetBlue

Sunday

American Airlines, JetBlue

American Airlines, JetBlue

See more direct flights

Reviews of the top airlines flying 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.
7.2
American AirlinesOverall score based on 11078 reviews
7.2Comfort
7.5Boarding
6.4Food
6.9Entertainment
8.0Crew
Airline reviews

Boarding was organized and timely. Food was mediocre, especially for first class travel.

8.0 ExcellentKrishna, Dec 2025
TPA - PHX
Read more American Airlines reviews

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

we were delayed because of some safety check that wasn't done or available

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

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.

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

Information on your arrival and departure airports