$79 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 9/20. 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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Cheap Flights from Pensacola to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$160
Albany
Albany1 stop$251
Boston
Boston1 stop$160
Albany
Albany1 stop$251

Book Cheap Pensacola to Massachusetts Plane Tickets

 
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

Wed, Sep 10 - Wed, Sep 17
Spirit Airlines Logo
4:44 pm - 11:57 pmPNS-BOS
6h 13m1 stop
Spirit Airlines Logo
6:10 am - 3:39 pmBOS-PNS
10h 29m1 stop
$160Spirit Airlines
Find Deal
Sat, Sep 6 - Tue, Sep 9
Spirit Airlines Logo
4:44 pm - 11:57 pmPNS-BOS
6h 13m1 stop
Spirit Airlines Logo
6:10 am - 3:39 pmBOS-PNS
10h 29m1 stop
$162Spirit Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
 Logo
7:10 pm - 7:57 pmPNS-BDL
23h 47m1 stop
 Logo
8:37 pm - 6:10 pmBDL-PNS
22h 33m1 stop
Wed, Oct 22 - Sat, Oct 25
American Airlines Logo
1:53 pm - 10:01 pmPNS-BDL
7h 08m1 stop
American Airlines Logo
1:52 pm - 6:22 pmBDL-PNS
5h 30m1 stop
$251American Airlines
Find Deal
Tue, Sep 16 - Wed, Oct 8
American Airlines Logo
3:57 pm - 11:59 pmPNS-ALB
7h 02m1 stop
American Airlines Logo
6:00 am - 10:13 amALB-PNS
5h 13m1 stop
$251American Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
 Logo
4:36 pm - 4:12 pmPNS-BDL
22h 36m1 stop
 Logo
11:44 am - 4:51 pmBDL-PNS
6h 07m1 stop
Tue, Sep 9 - Wed, Sep 10
Delta Logo
7:05 am - 1:36 pmPNS-BDL
5h 31m1 stop
Delta Logo
7:00 am - 1:08 pmBDL-PNS
7h 08m1 stop
$257Delta
Find Deal
Tue, Sep 9 - Wed, Sep 17
Delta Logo
6:00 am - 11:14 amPNS-ALB
4h 14m1 stop
Delta Logo
5:45 am - 11:34 amALB-PNS
6h 49m1 stop
$257Delta
Find Deal
Tue, Oct 28 - Sun, Nov 2
Southwest Logo
10:10 am - 9:15 pmPNS-BDL
10h 05m2 stops
Southwest Logo
5:00 am - 2:50 pmBDL-PNS
10h 50m2 stops
$362Southwest
Find Deal
Tue, Oct 28 - Sun, Nov 2
Southwest Logo
7:40 am - 2:30 pmPNS-BDL
5h 50m1 stop
Southwest Logo
12:20 pm - 9:55 pmBDL-PNS
10h 35m1 stop
$367Southwest
Find Deal
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

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 August and January, when the average cost of round-trip tickets is $436 and $391 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 4 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 1% increase in price.
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 4244 reviews
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

4.0 OkayJjais, Aug 2025MCO - BNA
Read more Southwest reviews

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

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.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

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.

Pretty good. The food was just mediocre, the boarding and crew were good.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

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 flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

For the minimalist experience, it is really a great ride-- feels a little like public transport i guess

I didn’t mind being delayed due to weather, but continuing to post (and not update) that we would be delayed until after the flight was already supposed to have taken off was a bit much. In the future, please announce the delay even if the time is still unknown.

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

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

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

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