$105 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 7/22. 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 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$212
Albany
Albany2 stops$734
Boston
Boston1 stop$212
Albany
Albany2 stops$734

Cheap Flights from Pensacola to Massachusetts

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pensacola to Massachusetts

Sat, Jul 26 - Sat, Aug 2
Spirit Airlines Logo
1:39 pm - 11:48 pmPNS-BOS
9h 09m1 stop
Spirit Airlines Logo
6:10 am - 6:29 pmBOS-PNS
13h 19m1 stop
$212Spirit Airlines
Find Deal
Wed, Jul 23 - Sat, Jul 26
Spirit Airlines Logo
1:53 pm - 11:48 pmPNS-BOS
8h 55m1 stop
Spirit Airlines Logo
6:10 am - 6:29 pmBOS-PNS
13h 19m1 stop
$222Spirit Airlines
Find Deal
Wed, Aug 27 - Sun, Aug 31
Delta Logo
6:00 am - 2:56 pmPNS-ORH
7h 56m2 stops
Delta Logo
3:55 pm - 9:46 pmORH-PNS
6h 51m2 stops
$337Delta
Find Deal
Sun, Jul 27 - Tue, Jul 29
Delta Logo
4:37 pm - 10:08 pmPNS-BDL
4h 31m1 stop
Delta Logo
5:04 pm - 9:42 pmBDL-PNS
5h 38m1 stop
$362Delta
Find Deal
Wed, Jul 23 - Sun, Jul 27
 Logo
11:13 am - 11:31 pmPNS-BDL
11h 18m1 stop
 Logo
6:20 am - 3:15 pmBDL-PNS
9h 55m1 stop
Tue, Jul 15 - Tue, Jul 22
 Logo
1:53 pm - 12:25 amPNS-BDL
9h 32m2 stops
 Logo
6:20 am - 10:41 pmBDL-PNS
17h 21m2 stops
Tue, Jul 15 - Tue, Jul 22
Southwest Logo
9:35 am - 4:05 pmPNS-BDL
5h 30m1 stop
Southwest Logo
5:25 am - 12:35 pmBDL-PNS
8h 10m1 stop
$427Southwest
Find Deal
Tue, Jul 15 - Tue, Jul 22
Southwest Logo
6:50 am - 3:45 pmPNS-BDL
7h 55m2 stops
Southwest Logo
5:25 am - 12:35 pmBDL-PNS
8h 10m1 stop
$432Southwest
Find Deal
Tue, Jul 15 - Sat, Jul 19
American Airlines Logo
6:09 am - 3:04 pmPNS-ORH
7h 55m1 stop
American Airlines Logo
3:29 pm - 9:00 pmORH-PNS
6h 31m1 stop
$442American Airlines
Find Deal
Tue, Jul 15 - Sat, Jul 19
American Airlines Logo
5:32 pm - 3:04 pmPNS-ORH
20h 32m2 stops
American Airlines Logo
3:29 pm - 10:45 amORH-PNS
20h 16m1 stop
$452American Airlines
Find Deal
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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 July, when tickets cost $352 (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 Saturdays 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 seasonAugust
Cheapest flight$105
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 1% 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.

Reviews of the 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 4273 reviews
8.2Boarding
7.0Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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:

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.

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.

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.

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.

Flight was on time and was not crowded. Flight attendants were very understanding of my wife’s back problems.

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Boarding east and ontime. Seat spacing was tight, and seats don’t recline.

The flight was canceled and was bounced around time wise with my elderly parents. That being said the gentleman in custody service was amazingly helpful

It amaze me how other airlines leave on time and Spirit always have some type of delay. I’ve flown with Spirit many times, but it reached a point I’d rather pay twice the amount and not deal with this corporation they never do nothing to reimburse people for their time or headaches.

Easy boarding and good flight. Need to work on the beverage and snack situation

Spirit charges you to breathe in their presence. They have you pick and buy your seat in advance and then I got bumped from the seat I paid for because THEY overbooked the flight by a dozen people. they do not provide any entertainment, they do not provide even a small cup of water - you have to pay for everything. I will never fly Spirit again.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

The flight, the pilot, the flight crew, and the ground personnel were all great, despite the sudden and lengthy FAA Ground Stop in Boston, which SPIRIT obviously had nothing to do with and no control over.

The seats! Do not nickel and dime! Be transparent about all your fees!

Everything you need to know for your flight from Pensacola to Massachusetts

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