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$65+ Cheap flights from Florida Keys to Boston (BOS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Oct 24 — Oct 311
Fri 10/24
Fri 10/31
1 adult, Economy
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Cheap flight deals from Florida Keys to Boston

Keep the following information in mind while searching for Florida Keys to Boston flight deals. Data was last updated September 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$105
(Frontier)

One-way from

$65
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$300
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
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From Florida Keys to Boston Logan Intl
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One-way flight from Florida Keys to Boston Logan Intl
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Highest demand for flights based on searches. 15% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Florida Keys to Boston

Cheapest flights from Florida Keys to Boston
Explore the most affordable flight options available from Florida Keys to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2025.

This Frontier deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/197:24 amMIA - BOS
Nonstop3h 25mFrontier
Thu 10/2311:44 amBOS - MIA
Nonstop3h 36mFrontier
Deal found 9/23$105
This Booking.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:00 amMIA - BOS
Nonstop3h 25mSpirit Airlines
Thu 12/1112:20 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
Deal found 9/22$106
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/612:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Fri 10/174:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Deal found 9/22$114
This Booking.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:24 amMIA - BOS
Nonstop3h 25mFrontier
Sun 10/268:12 amBOS - MIA
1 stop7h 51mFrontier
Deal found 9/22$117
This Booking.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:24 amMIA - BOS
Nonstop3h 25mFrontier
Thu 10/309:39 amBOS - MIA
1 stop11h 43mFrontier
Deal found 9/23$118
This Booking.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/127:51 amMIA - BOS
1 stop23h 36mFrontier
Thu 10/1611:44 amBOS - MIA
Nonstop3h 36mFrontier
Deal found 9/23$119
This Cheapflightsfares deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/29:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
Mon 10/64:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Deal found 9/22$122
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/612:40 pmMIA - BOS
Nonstop3h 16mMultiple Airlines
Thu 10/1612:22 pmBOS - MIA
1 stop28h 34mMultiple Airlines
Deal found 9/22$123
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/41:55 pmMIA - BOS
1 stop18h 48mMultiple Airlines
Mon 10/64:54 pmBOS - MIA
Nonstop3h 38mMultiple Airlines
Deal found 9/21$124
This Priceline deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:24 amMIA - BOS
Nonstop3h 25mMultiple Airlines
Fri 10/174:54 pmBOS - MIA
Nonstop3h 38mMultiple Airlines
Deal found 9/23$125
This Flightnetwork deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:32 pmMIA - BOS
1 stop12h 04mMultiple Airlines
Mon 10/204:54 pmBOS - MIA
Nonstop3h 38mMultiple Airlines
Deal found 9/23$128
This JetBlue deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:45 pmEYW - BOS
Nonstop3h 30mJetBlue
Sun 11/28:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 9/23$207

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys to Boston 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, Cheapflights users made 2,558,603 searches. Data last updated September 24, 2025.
Use the filters below to find and compare flights from Florida Keys to Boston that are best for you.

Fly from

Florida Keys

Fly to

Boston

Route

Depart

Return

Price

MiamiBoston

MIA - BOS

MIABOS

Miami

Wed 10/8

3:33 pm-10:27 pm

1 stop6h 54m

Boston Logan Intl

Tue 10/14

7:35 am-11:10 am

Nonstop3h 35m

$157

MiamiBoston

MIA - BOS

MIABOS

Miami

Sat 11/15

6:55 am-10:19 am

Nonstop3h 24m

Boston Logan Intl

Sun 11/23

3:10 pm-6:47 pm

Nonstop3h 37m

$167

MiamiBoston

MIA - BOS

MIABOS

Miami

Wed 12/3

3:30 pm-9:23 pm

1 stop5h 53m

Boston Logan Intl

Sat 12/6

7:59 pm-11:36 pm

Nonstop3h 37m

$169

MiamiBoston

MIA - BOS

MIABOS

Miami

Fri 11/21

6:55 am-10:18 am

Nonstop3h 23m

Boston Logan Intl

Mon 11/24

10:30 am-6:36 pm

1 stop8h 06m

$197

MiamiBoston

MIA - BOS

MIABOS

Miami

Thu 11/13

4:42 pm-10:48 pm

1 stop6h 06m

Boston Logan Intl

Sat 11/15

5:30 am-2:37 pm

2 stops9h 07m

$202

MiamiBoston

MIA - BOS

MIABOS

Miami

Wed 10/15

5:25 pm-11:49 pm

1 stop6h 24m

Boston Logan Intl

Mon 10/20

7:35 am-11:10 am

Nonstop3h 35m

$203

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 10/10

1:04 pm-4:56 pm

Nonstop3h 52m

Boston Logan Intl

Mon 10/13

8:10 am-12:09 pm

Nonstop3h 59m

$207

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 10/31

12:45 pm-4:15 pm

Nonstop3h 30m

Boston Logan Intl

Sun 11/2

8:00 am-11:53 am

Nonstop3h 53m

$207

MiamiBoston

MIA - BOS

MIABOS

Miami

Fri 11/14

7:30 pm-1:30 am

1 stop6h 00m

Boston Logan Intl

Sun 11/23

9:59 am-4:10 pm

1 stop6h 11m

$213

MiamiBoston

MIA - BOS

MIABOS

Miami

Fri 12/19

6:15 am-1:45 pm

1 stop7h 30m

Boston Logan Intl

Tue 12/23

3:35 pm-10:55 pm

1 stop7h 20m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/22

Showing 1-10 of 39 results
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Best time to book a flight from Florida Keys to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Florida Keys with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Boston

What is the cheapest month to book a flight from Florida Keys to Boston?

Currently, January is the cheapest month in which you can book a flight from Florida Keys to Boston (average of $218). Flying from Florida Keys to Boston in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EOA to BOS?

Find hourly flight availability from Florida Keys to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 24, 2025.

When flying from Florida Keys to Boston, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated September 24, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Florida Keys to Boston to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,911 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,042 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.8
Fair
3,163 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Boston from Florida Keys?

    Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Florida Keys to Boston. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

  • How long is the flight from Florida Keys to Boston?

    Departing from Florida Keys to Boston will take you 3h 52m. Florida Keys and Boston are separated by a distance of 1374 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Florida Keys to Boston one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $71. However, be on the lookout for offers from Delta and JetBlue, as they are both options that can get you from Florida Keys to Boston for a low price.

  • What are the cheapest flights from Florida Keys to Boston?

    Looking for the cheapest flight from Florida Keys to Boston? While on average our users pay $163, our data indicates the cheapest price to be $125. The most popular route (Miami - Boston Logan Intl), is priced around $95.

  • Can I find deals for flights from Florida Keys to Boston that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Boston.

  • Can I find deals for business class flights from Florida Keys to Boston?

    Yes. Cheapflights offers flight deals from Florida Keys to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Florida Keys to Boston?

    Currently, January is the cheapest month in which you can book a flight from Florida Keys to Boston (average of $218). Flying from Florida Keys to Boston in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Alternative routes for Florida Keys to Boston

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Florida Keys to Boston

Discover the top 3 airlines that operate flights from Florida Keys to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$399FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$498FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$258Average$343FlexibilityNo cancel feeOn-time71%

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