$78 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 4/4. 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

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$203
Albany
Albany1 stop$280
Boston
Boston1 stop$203
Albany
Albany1 stop$280

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

Sat, Apr 4 - Sun, Apr 5
Multiple Airlines Logo
7:00 am - 6:09 pm
PNS
-
BOS
10h 09m
1 stop
Multiple Airlines Logo
11:31 am - 9:14 pm
BOS
-
PNS
10h 43m
1 stop
$203Multiple Airlines
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
11:18 am - 5:23 pm
PNS
-
BDL
5h 05m
1 stop
Multiple Airlines Logo
8:42 pm - 10:29 pm
BDL
-
PNS
26h 47m
1 stop
$211Multiple Airlines
Sat, Apr 4 - Tue, Apr 7
Spirit Airlines Logo
7:00 am - 6:09 pm
PNS
-
BOS
10h 09m
1 stop
Spirit Airlines Logo
9:45 am - 9:14 pm
BOS
-
PNS
12h 29m
1 stop
$221Spirit Airlines
Thu, Apr 9 - Sun, Apr 12
Spirit Airlines Logo
2:15 pm - 11:59 pm
PNS
-
BOS
8h 44m
1 stop
Spirit Airlines Logo
5:45 am - 1:16 pm
BOS
-
PNS
8h 31m
1 stop
$229Spirit Airlines
Fri, Sep 11 - Tue, Sep 15
Breeze Airways Logo
8:58 am - 10:21 pm
PNS
-
BDL
12h 23m
2 stops
Breeze Airways Logo
7:05 am - 9:50 am
BDL
-
PNS
27h 45m
1 stop
$282Breeze Airways
Wed, Apr 15 - Wed, Apr 22
Breeze Airways Logo
11:18 am - 5:23 pm
PNS
-
BDL
5h 05m
1 stop
Breeze Airways Logo
8:05 am - 8:55 am
BDL
-
PNS
25h 50m
1 stop
$293Breeze Airways
Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
5:07 am - 1:26 pm
PNS
-
ALB
7h 19m
1 stop
American Airlines Logo
2:11 pm - 6:12 pm
ALB
-
PNS
5h 01m
1 stop
$351American Airlines
Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
5:07 am - 2:15 pm
PNS
-
ALB
8h 08m
2 stops
American Airlines Logo
2:11 pm - 6:12 pm
ALB
-
PNS
5h 01m
1 stop
$356American Airlines
Tue, Jun 9 - Thu, Jun 18
Delta Logo
7:00 am - 2:39 pm
PNS
-
ORH
6h 39m
2 stops
Delta Logo
3:18 pm - 11:05 am
ORH
-
PNS
20h 47m
1 stop
$403Delta
Tue, Jun 9 - Thu, Jun 18
Delta Logo
6:00 am - 2:39 pm
PNS
-
ORH
7h 39m
2 stops
Delta Logo
3:18 pm - 11:24 pm
ORH
-
PNS
9h 06m
2 stops
$409Delta
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 $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 October, when tickets cost $350 (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 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$78
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 15% 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.

  • How many flights are there between Pensacola and Massachusetts per day?

    There is a maximum of 1 nonstop flight a day that takes off from Pensacola and lands in Massachusetts, with an average flight time of 3h 06m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 3 flights.

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 4324 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

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.

10.0 ExcellentEric, Mar 2026
MCO - BNA
Read more Southwest reviews

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.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

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.

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.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

The flight was great as well as the airline staff

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

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.

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

The flight attendants and the service is getting worse by the day.

Other than nearly three hour delay for maintenance issues, everything went smooth

we boarded the plane and then sat for OVER AN HOUR on it, first waiting for fuel and then the crew timed out. the flight kept getting delayed longer and longer, a 9:30pm flight is still on the ground at 1:15am.

Smooth flight staff very friendly and we arrived 15 mins earlier

Return flight was canceled. Needed to reschedule with another airline the next day. Cost an an additional $84. At another airport 45 miles further away

Bad airline to travel with my flight was delayed for more than 3 hours they act like it’s normal

Like Spirit but bad that you have to pay for water 🙃

My flight was ultimately cancelled but the lack of updates and professionalism from the crew leading up to the cancellation announcement was frustrating for all passengers.

Delay due to personnel issues on Spirit’s end. Original departure time 9:30pm. Took off at 2:15am. Lost an entire night’s sleep bc Spirit couldn’t get a crew together. Very poor.

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

I’m still waiting to get on the flight. No one knows what’s happening. The passengers have gotten no updates. We have been up all night and waiting at the airport. This is no way to operate and we should be refunded for this lack of respect for their passengers.

Flight was delayed, then undelayed, then delayed again. Gate was changed to the other side of the airport. Horrible seats with no screens. Spirit os truly awful, even for a budget option.

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

Information on your arrival and departure airports