$83 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 5/7. 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, 0 bags

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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$172
Albany
Albany1 stop$298
Boston
Boston1 stop$172
Albany
Albany1 stop$298

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, Apr 29 - Mon, May 4
Multiple Airlines Logo
6:36 am - 12:43 pm
PNS
-
BDL
29h 07m
1 stop
Multiple Airlines Logo
8:42 pm - 3:53 pm
BDL
-
PNS
20h 11m
1 stop
$159Multiple Airlines
Wed, May 6 - Wed, May 13
Multiple Airlines Logo
4:48 pm - 9:12 am
PNS
-
BOS
15h 24m
1 stop
Multiple Airlines Logo
10:07 am - 1:59 pm
BOS
-
PNS
28h 52m
1 stop
$172Multiple Airlines
Wed, May 6 - Wed, May 13
Multiple Airlines Logo
4:48 pm - 9:12 am
PNS
-
BOS
15h 24m
1 stop
Multiple Airlines Logo
9:20 am - 1:59 pm
BOS
-
PNS
29h 39m
1 stop
$174Multiple Airlines
Wed, May 6 - Wed, May 13
Multiple Airlines Logo
4:48 pm - 9:12 am
PNS
-
BOS
15h 24m
1 stop
Multiple Airlines Logo
10:07 am - 1:59 pm
BOS
-
PNS
28h 52m
1 stop
$183Multiple Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
4:48 pm - 9:12 am
PNS
-
BOS
15h 24m
1 stop
Multiple Airlines Logo
10:07 am - 3:53 pm
BOS
-
PNS
6h 46m
1 stop
$190Multiple Airlines
Wed, Sep 9 - Sat, Sep 12
Breeze Airways Logo
10:30 am - 6:18 pm
PNS
-
BDL
6h 48m
1 stop
Breeze Airways Logo
6:00 am - 12:45 pm
BDL
-
PNS
7h 45m
1 stop
$234Breeze Airways
Wed, Sep 9 - Sat, Sep 12
Breeze Airways Logo
10:30 am - 6:18 pm
PNS
-
BDL
6h 48m
1 stop
Breeze Airways Logo
6:00 am - 12:45 pm
BDL
-
PNS
7h 45m
1 stop
$235Breeze Airways
Tue, May 5 - Tue, May 12
American Airlines Logo
5:55 pm - 11:57 pm
PNS
-
ALB
5h 02m
1 stop
American Airlines Logo
2:45 pm - 9:24 pm
ALB
-
PNS
7h 39m
1 stop
$351American Airlines
Tue, May 5 - Tue, May 12
American Airlines Logo
7:11 am - 5:00 pm
PNS
-
ALB
8h 49m
2 stops
American Airlines Logo
5:30 pm - 9:24 pm
ALB
-
PNS
4h 54m
1 stop
$356American Airlines
Fri, Aug 14 - Mon, Aug 17
Delta Logo
7:00 am - 2:39 pm
PNS
-
ORH
6h 39m
2 stops
Delta Logo
3:18 pm - 10:01 pm
ORH
-
PNS
7h 43m
2 stops
$458Delta
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.

How much is a round-trip flight from Pensacola to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Pensacola to Massachusetts departing in May.

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 $279 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 $279.

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 May, when tickets cost $348 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $463 and $458 respectively.

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, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$83
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 3% 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.

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 4334 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

2.0 MediocreDavid, Apr 2026
MCO - MCI
Read more Southwest reviews

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

I have never been assaulted they way I was today in Charlotte - shame on American

The staff are very, very professional. It's what flying should feel like.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

The flight attendant in business class was excellent! Professional, friendly and attentive.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

It was great. Smooth flight, comfortable, left on time and landed on time.

The attendant at the gate was not helpful at all and she was rude when we asked why the flight was delayed.

a weekend long saga that ultimately led to a canceled trip. totally unreliable.

Long long delay, no AC while delayed, gate changes, just for the most uncomfortable flight of your life.

Everything was smooth sailing. Great crew, easy flight and was surprised with an upgraded seat. Thank you all!

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

I truly admired that the last minute flight attendants were willing to come to serve flight # 1465 and think they should be extra compensated. Doesn't have to beonetary a star a permanent position with Spirit as long as she flies etc. They were o so pleasant and accommodating. 😊😊. Please also serve water. Plain unadulterated water 💧! Invest in a filter of your own the cost of bottles are a penny on the dollar and you could have a plug on advertising with labeling. This could be hilarious "WATER TO REFREST THE SPIRIT FROM SPIRIT ITSELF!" - Free idea!😄😄😄. Anyway overall, though a tad late the flight met expectations. Thanks you Spirit, for everything.

The ticket price are reasonable, however, they can do better with the price on the luggage. Overall, I will continue using spirit.

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is always late. Every single time. Always a different reason

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

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

Information on your arrival and departure airports