$251 Find Cheap Flights from Tallahassee to Massachusetts

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Massachusetts departing on 8/27. 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 Tallahassee 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 Tallahassee to Massachusetts, as well as popular online travel agencies
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Cheap Flights from Tallahassee to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$251
Albany
Albany1 stop$311
Boston
Boston1 stop$251
Albany
Albany1 stop$311

Book Cheap Tallahassee 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 Tallahassee 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 Tallahassee to Massachusetts

Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
12:47 pm - 11:54 pm
TLH
-
BOS
11h 07m
1 stop
Multiple Airlines Logo
12:51 pm - 8:58 am
BOS
-
TLH
20h 07m
1 stop
$251Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
12:47 pm - 11:54 pm
TLH
-
BOS
11h 07m
1 stop
Multiple Airlines Logo
9:15 am - 8:58 am
BOS
-
TLH
23h 43m
2 stops
$297Multiple Airlines
Wed, May 13 - Tue, May 19
Delta Logo
7:07 pm - 11:58 pm
TLH
-
ALB
4h 51m
1 stop
Delta Logo
6:00 am - 11:05 am
ALB
-
TLH
5h 05m
1 stop
$311Delta
Sat, May 23 - Sat, May 30
Delta Logo
5:23 pm - 12:33 am
TLH
-
BDL
7h 10m
1 stop
Delta Logo
6:00 am - 11:05 am
BDL
-
TLH
5h 05m
1 stop
$311Delta
Wed, May 13 - Tue, May 19
Delta Logo
11:51 am - 11:18 pm
TLH
-
ALB
11h 27m
2 stops
Delta Logo
6:00 am - 11:05 am
ALB
-
TLH
5h 05m
1 stop
$316Delta
Tue, Aug 4 - Sat, Aug 8
Multiple Airlines Logo
2:17 pm - 11:54 pm
TLH
-
BOS
9h 37m
1 stop
Multiple Airlines Logo
6:00 am - 7:28 am
BOS
-
TLH
25h 28m
2 stops
$347Multiple Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
3:27 pm - 10:02 pm
TLH
-
BDL
6h 35m
2 stops
American Airlines Logo
6:01 am - 11:35 am
BDL
-
TLH
5h 34m
1 stop
$372American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
6:21 pm - 11:57 pm
TLH
-
BDL
5h 36m
1 stop
American Airlines Logo
9:25 am - 5:51 pm
BDL
-
TLH
8h 26m
2 stops
$404American Airlines
Sat, Jul 4 - Wed, Jul 15
American Airlines Logo
6:00 am - 2:11 pm
TLH
-
BDL
8h 11m
2 stops
American Airlines Logo
2:09 pm - 10:05 pm
BDL
-
TLH
7h 56m
1 stop
$428American Airlines
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
6:00 am - 2:11 pm
TLH
-
BDL
8h 11m
2 stops
American Airlines Logo
9:25 am - 5:51 pm
BDL
-
TLH
8h 26m
2 stops
$466American Airlines
Booking Insights

KAYAK's insights & trends for Tallahassee to Massachusetts flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tallahassee 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 Tallahassee to Massachusetts is October, when tickets cost $477 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $649 and $623 respectively.

Good to know

Low seasonJanuary
Cheapest flight$251
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Tallahassee to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Tallahassee 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 Tallahassee to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Tallahassee 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 Tallahassee 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 Tallahassee 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 Tallahassee 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 Tallahassee 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 airlines flying from Tallahassee to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Tallahassee 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 Tallahassee 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.
7.9
DeltaOverall score based on 8293 reviews
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Mar 2026
TPA - ATL
Read more Delta reviews

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(?)

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

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

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

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

Information on your arrival and departure airports