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$69+ Cheap flights from Clearwater, FL to Massachusetts

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Cheap flight deals from Clearwater to Massachusetts

Keep the following information in mind while searching for Clearwater to Massachusetts flight deals. Data was last updated October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$95
(Southwest)

One-way from

$69
(Delta)

Popular in

October

Cheapest in

January

Average price

$261
Provider with most accurate pricing for Tampa-Boston Logan Intl flight deals.
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From Clearwater to Massachusetts
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One-way flight from Clearwater to Massachusetts
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Highest demand for flights based on searches. 11% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Clearwater to Massachusetts

Cheapest flights from Clearwater to Massachusetts
Explore the most affordable flight options available from Clearwater to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:40 amTPA - BDL
Nonstop2h 40mSouthwest
Sat 12/137:20 amBDL - TPA
Nonstop3h 10mSouthwest
Deal found 10/19$95
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:40 amTPA - BDL
Nonstop2h 40mSouthwest
Tue 12/92:00 pmBDL - TPA
Nonstop3h 05mSouthwest
Deal found 10/19$100
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:00 amTPA - BOS
Nonstop3h 02mDelta
Sun 11/167:20 amBOS - TPA
Nonstop3h 36mDelta
Deal found 10/19$117
This Breeze Airways deal was found by Cheapflights users on 10/18. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:50 amTPA - BDL
Nonstop2h 55mBreeze Airways
Mon 12/86:00 amBDL - TPA
Nonstop3h 10mBreeze Airways
Deal found 10/18$118
This Kissandfly.com deal was found by Cheapflights users on 10/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:19 amTPA - BOS
Nonstop2h 58mJetBlue
Mon 11/106:00 amBOS - TPA
Nonstop3h 28mJetBlue
Deal found 10/19$124
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:50 amTPA - BOS
2 stops6h 55mSouthwest
Tue 12/165:30 amBOS - TPA
1 stop7h 10mSouthwest
Deal found 10/19$126
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/134:25 pmTPA - BOS
1 stop7h 30mDelta
Sat 11/158:26 pmBOS - TPA
Nonstop3h 33mDelta
Deal found 10/19$127
This Breeze Airways deal was found by Cheapflights users on 10/18. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:50 amTPA - BDL
Nonstop2h 55mBreeze Airways
Mon 11/176:00 amBDL - TPA
Nonstop3h 10mBreeze Airways
Deal found 10/18$128
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Thu 11/612:14 pmTPA - BOS
1 stop11h 45mMultiple Airlines
Sun 11/910:04 amBOS - TPA
1 stop7h 33mMultiple Airlines
Deal found 10/17$131
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Fri 11/76:44 pmTPA - BOS
1 stop5h 15mMultiple Airlines
Sun 11/98:36 amBOS - TPA
1 stop23h 28mMultiple Airlines
Deal found 10/19$132
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:15 pmTPA - BOS
1 stop8h 00mSouthwest
Wed 12/177:45 amBOS - TPA
1 stop5h 55mSouthwest
Deal found 10/19$133
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/156:50 pmTPA - BOS
1 stop14h 10mFrontier
Sun 12/711:28 amBOS - TPA
1 stop12h 48mFrontier
Deal found 10/18$134

Cheapflights Fare Finder

 
Customize your flight search to find flights from Clearwater to Massachusetts 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 October 20, 2025.
Use the filters below to find and compare flights from Clearwater to Massachusetts that are best for you.

Fly from

Clearwater

Fly to

Massachusetts

Route

Depart

Return

Price

TampaHartford

TPA - BDL

TPABDL

Tampa

Tue 12/9

3:55 pm-10:05 pm

1 stop6h 10m

Hartford Bradley Intl

Sat 12/13

9:45 am-4:40 pm

1 stop6h 55m

$114

TampaBoston

TPA - BOS

TPABOS

Tampa

Thu 11/6

6:00 am-8:55 am

Nonstop2h 55m

Boston Logan Intl

Sat 11/15

8:10 pm-11:41 pm

Nonstop3h 31m

$117

TampaBoston

TPA - BOS

TPABOS

Tampa

Thu 11/6

6:00 am-8:55 am

Nonstop2h 55m

Boston Logan Intl

Mon 11/10

6:00 am-9:28 am

Nonstop3h 28m

$117

TampaHartford

TPA - BDL

TPABDL

Tampa

Mon 1/26

3:55 pm-9:50 pm

1 stop5h 55m

Hartford Bradley Intl

Mon 2/2

3:30 pm-9:35 pm

1 stop6h 05m

$125

TampaBoston

TPA - BOS

TPABOS

Tampa

Thu 11/13

8:08 pm-1:30 am

1 stop5h 22m

Boston Logan Intl

Sun 11/16

7:20 am-10:56 am

Nonstop3h 36m

$127

TampaHartford

TPA - BDL

TPABDL

Tampa

Thu 1/8

7:06 pm-10:04 pm

Nonstop2h 58m

Hartford Bradley Intl

Thu 1/15

3:00 pm-6:26 pm

Nonstop3h 26m

$133

TampaBoston

TPA - BOS

TPABOS

Tampa

Wed 11/5

6:55 pm-1:18 am

1 stop6h 23m

Boston Logan Intl

Tue 11/11

3:30 pm-7:01 pm

Nonstop3h 31m

$137

TampaHartford

TPA - BDL

TPABDL

Tampa

Fri 12/5

9:45 am-12:28 pm

Nonstop2h 43m

Hartford Bradley Intl

Sun 12/7

1:30 pm-4:35 pm

Nonstop3h 05m

$137

TampaHartford

TPA - BDL

TPABDL

Tampa

Fri 10/31

9:50 am-12:45 pm

Nonstop2h 55m

Hartford Bradley Intl

Mon 11/3

6:00 am-9:10 am

Nonstop3h 10m

$143

TampaBoston

TPA - BOS

TPABOS

Tampa

Sat 1/10

8:10 am-4:10 pm

1 stop8h 00m

Boston Logan Intl

Sat 1/17

5:45 am-3:50 pm

2 stops10h 05m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 60 results
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Best time to book a flight from Clearwater to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Clearwater 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 Clearwater to Massachusetts

What is the cheapest month to book a flight from Clearwater to Massachusetts?

Currently, February is the cheapest month in which you can book a flight from Clearwater to Massachusetts (average of $37). Flying from Clearwater to Massachusetts in July is currently the most expensive (average of $100). 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 CL9 to MA?

Find hourly flight availability from Clearwater to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Clearwater to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Clearwater to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Clearwater to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Clearwater to Massachusetts flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Clearwater to Massachusetts

Explore weekly flight availability from Clearwater to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 20, 2025.

The most flights from CL9 to USMA are scheduled on a Sunday (64 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (31 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated October 20, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from Clearwater to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,976 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

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
7.9
Good
7,976 reviews
Delta
7.9
Good
7,976 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

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
11,026 reviews
Delta
7.9
Good
7,976 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

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
2,907 reviews
Delta
7.9
Good
7,976 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

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
8,104 reviews
Delta
7.9
Good
7,976 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

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
3,134 reviews
Delta
7.9
Good
7,976 reviews

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

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 Clearwater to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Clearwater to Massachusetts?

    For as low as $117, Southwest can have you in Massachusetts from Clearwater in 2h 55m. Airlines will cover a distance of 1185 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Clearwater to Massachusetts one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $69. Breeze Airways flights start at $74 while deals on Southwest start at $79 one-way.

  • What are the most popular routes from Clearwater to Massachusetts?

    While some choose either Tampa - Hartford Bradley Intl or Tampa - Albany Intl, Tampa - Boston Logan Intl is the most popular route from Clearwater to Massachusetts.

  • What are the most reliable airlines from Clearwater to Massachusetts?

    Before booking your flight to Massachusetts from Clearwater, check out the most reliable airlines to get you to your destination on time: Korean Air (95%), Japan Airlines (91%), Frontier( 90%).

  • What are the cheapest flights from Clearwater to Massachusetts?

    While on average a flight from Clearwater to Massachusetts is generally $1,241, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Tampa - Boston Logan Intl), you can expect to pay $117 for that flight.

  • Can I find deals for flights from Clearwater to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Clearwater to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Clearwater to Massachusetts?

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

  • Can I find deals for business class flights from Clearwater to Massachusetts?

    Yes. Cheapflights offers flight deals from Clearwater to Massachusetts 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 Clearwater to Massachusetts?

    Currently, February is the cheapest month in which you can book a flight from Clearwater to Massachusetts (average of $37). Flying from Clearwater to Massachusetts in July is currently the most expensive (average of $100). 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.

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Alternative routes for Clearwater to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Clearwater to Massachusetts

Discover the top 8 airlines that operate flights from Clearwater to Massachusetts. 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$39Average$127FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$53Average$174FlexibilityNo cancel feeOn-time88%
DeltaCheapest$78Average$261FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$107Average$296FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$156Average$294FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$158Average$310FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$336FlexibilityNo cancel feeOn-time69%

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