$86 Find Cheap Flights from Pensacola to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pensacola to Massachusetts departing on 5/29. 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.
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KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston1 stop$175
Albany
Albany1 stop$285
Boston
Boston1 stop$175
Albany
Albany1 stop$285

Cheap Flight Deals from Pensacola to Massachusetts (PNS-USMA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pensacola to Massachusetts 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.

Recent round-trip flight deals from Pensacola to Massachusetts

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Pensacola to Massachusetts.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
4:35 pm - 11:29 pmPNS-BOS
5h 54m1 stop
Spirit Airlines Logo
5:45 am - 5:09 pmBOS-PNS
12h 24m1 stop
$175Spirit Airlines
Find Deal
Thu, May 29 - Mon, Jun 2
Spirit Airlines Logo
4:35 pm - 3:44 pmPNS-BOS
22h 09m1 stop
Spirit Airlines Logo
5:42 pm - 10:20 pmBOS-PNS
5h 38m1 stop
$176Spirit Airlines
Find Deal
Fri, May 30 - Tue, Jun 3
Delta Logo
10:56 am - 4:10 pmPNS-BDL
4h 14m1 stop
Delta Logo
7:00 am - 10:44 amBDL-PNS
4h 44m1 stop
$285Delta
Find Deal
Wed, Jul 2 - Wed, Sep 3
Delta Logo
4:07 pm - 11:56 pmPNS-ALB
6h 49m1 stop
Delta Logo
12:41 pm - 4:58 pmALB-PNS
5h 17m1 stop
$285Delta
Find Deal
Tue, Jul 1 - Wed, Jul 9
United Airlines Logo
3:05 pm - 11:44 pmPNS-BOS
7h 39m1 stop
United Airlines Logo
1:35 pm - 10:14 pmBOS-PNS
9h 39m1 stop
$297United Airlines
Find Deal
Wed, Jun 4 - Thu, Aug 14
American Airlines Logo
2:38 pm - 12:52 pmPNS-ORH
21h 14m2 stops
American Airlines Logo
3:40 pm - 10:45 amORH-PNS
20h 05m1 stop
$310American Airlines
Find Deal
Tue, Jul 1 - Tue, Jul 8
Southwest Logo
1:45 pm - 11:00 pmPNS-BOS
8h 15m1 stop
Southwest Logo
5:00 am - 9:15 amBOS-PNS
5h 15m1 stop
$319Southwest
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
1:45 pm - 11:00 pmPNS-BOS
8h 15m1 stop
Southwest Logo
5:35 am - 1:00 pmBOS-PNS
8h 25m2 stops
$324Southwest
Find Deal
Thu, Aug 21 - Mon, Aug 25
American Airlines Logo
11:18 am - 4:26 pmPNS-ALB
4h 08m1 stop
American Airlines Logo
5:12 pm - 9:07 pmALB-PNS
4h 55m1 stop
$325American Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
United Airlines Logo
7:00 am - 4:43 pmPNS-BOS
8h 43m2 stops
United Airlines Logo
5:30 am - 1:59 pmBOS-PNS
9h 29m2 stops
$329United Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
Useful Info

KAYAK's insights & trends for Pensacola to Massachusetts flights

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

What is the cheapest Pensacola to Massachusetts flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Pensacola to Massachusetts.

The cheapest ticket to Massachusetts from Pensacola found in the last 72 hours was to Boston, at $148 round-trip. The most popular route is from Pensacola (PNS) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $148.

What is the cheapest month to fly from Pensacola to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Massachusetts, 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 Pensacola to Massachusetts is June, when tickets cost $325 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $386 and $386 respectively.

What’s the cheapest day of the week to fly from Pensacola to Massachusetts?

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

Your flight ticket price will generally be cheaper if you fly to Massachusetts on a Tuesday and more expensive on a Monday. On your return trip to Pensacola, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

How far in advance should I book a flight from Pensacola to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pensacola to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Pensacola to Massachusetts, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonFebruary
High seasonOctober
Cheapest flight$86
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Pensacola to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Pensacola to Massachusetts?

    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 Pensacola to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pensacola to Massachusetts 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 Pensacola to Massachusetts?

    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 Pensacola to Massachusetts 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 Pensacola to Massachusetts?

    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 Pensacola to Massachusetts 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 Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the morning, when round-trip flights cost $193 on average. Morning departures are around 49% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $382.

Top 4 airlines serving from Pensacola to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Pensacola to Massachusetts. 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 Pensacola to Massachusetts? 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
SouthwestOverall score based on 4294 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

The flight was delayed about 20 minutes, but this was an evening flight, so it comes as no surprise. This flight came a good 1.5 days ahead of hurricane Helene which was still far out in the gulf. However, the flight never removed the seated buckle light. The staff announced from the beginning that due to the bad weather (I suppose the hurricane a day and a half away) they would have to do an abbreviated service with water and a snack. I am fine with their water and snack offering, but this was one of the smoothest flights I've had in years. If Southwest believes a flight like this requires everyone to remain seated, then all of their flights should remain buckled for the entire flight. I cannot help but wonder if things like this are a sneaky way to cut back on expenses since the airline is currently under a lot of pressure to reduce costs.

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.

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.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

It was terrible, if they ran flights on time it would make a big difference.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

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.

the pilot that landed this flight in Philadelphia did an amazing job, the weather was absolutely terrible and we landed safely.

Per usual, flight status, staff courtesy and professionalism were excellent

The seats were crammed and the guy in front of me wouldn't stop reclining. If AA is cramming extra rows in, they need to take away the reclining in coach. My knees were smashed for 4 1/2 hours and I was very close to confronting the passenger in front of me.

AA can't control the weather. But the airplane was hot and stuffy while stuck on the runway with a broken entertainment system.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

I paid for streaming wifi and the connection was poor.

We had an 8 hr delay so it was not good

Easy boarding. Met expectations for a 2-3 hour flight. Early arrival at DFW caused a 39 minute delay on the tarmac in getting to our gate. 😏 overall, good flight.

Very efficient process and boarding, seats felt standard. Flight conditions from take off to landing had been very smooth. Alcohol on the menu however was not available… Will fly Spirit in the future for the price, you can’t really complain if you fly light.

Bad experience. Unhappy with the changing of flight times and one particular flight attendant (Bartholomew) on our flight from Orlando to Detroit. Traveling with a large family of 7, including our 18 month old, can be arduous but when the airline changes your flight time from landing at 9:30 pm to landing after midnight, this becomes much more difficult. When our 18 month old was predictably over tired and fussy, my wife and I tried to move to an open row so we can console her more effectively. The flight attendent rebuked us and said we could not sit in an exit row. We were not planning on sitting there for more than a few minutes but just to have space to console our screaming 18 month old. Spirit did not allow for a family friendly trip. Likely will be choosing a different airline next time.

I book a filght for me and my daughter from Miami home to Las Vegas and getting her checked in was awful the lady at the baggage check in was horrible!!! She was the rudest person I have ever encountered in my entire life!!!! My daughter dose not speak Spanish and so I was trying to translate for her but the woman would not let me so my daughter was 100 💯 confused because she could not understand what was going on or being said at all horrible absolutely horrible and rude extremely stressful worst experience ever!!!!!!! And then we were actually told by other air port staff not to complain because if we did sprint would make sure we miss our flight ✈️ that they do it all the time 😧

This was my first experience with Spirit. The flight was originally delayed because of mechanical problems. There was a major storm moving through our area later in the day. Spirit kept changing the gate and taking the plane for other flights. They did this 6 times until we left 7 hours later, right at the worse time. I am sure it is because they originally delayed the flight through their fault. They would have had to pay for everybody's hotel and later flight. It was a money decision. The pilot did an exceptional job flying and landing the plane in horrific weather. It was one of the roughest and shakiest landings that I have ever done in my extensive flying experience. I just can never go through this discount BS again. Spirit gave us a $30 voucher each for next travel and a $12 meal voucher... but that's nothing compared to sitting in an airport for 7 hours.

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