$64 Find Cheap Flights from Maryland to Massachusetts

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Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Reagan Washington National Airport to West Tisbury

FAQs for booking flights from Maryland to Massachusetts

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Maryland 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 Maryland 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 Maryland 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 Maryland 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 Maryland to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Massachusetts?

    Maryland and Massachusetts are connected by different airlines. The airlines that fly that route the most regularly are Southwest (52 flights per week), Delta (22 flights per week), and Spirit Airlines (12 flights per week).

  • How many airports are there in Massachusetts?

    There are 6 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 95% of all flights arriving there.

  • Which is the cheapest airport to fly into in Massachusetts?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $171.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Thursday where round-trip tickets can be as cheap as $238. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $438 on average.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $223 on average. Morning departures are around 46% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $472.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Maryland found in the last 72 hours was to Boston, at $95 round-trip. The most popular route is Baltimore (BWI) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $95.

  • What is the cheapest month to fly from Maryland to Massachusetts?

    The cheapest month for flights from Maryland to Massachusetts is July, when tickets cost $195 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $314 and $295 respectively.

  • How far in advance should I book a flight from Maryland to Massachusetts?

    To get a below average price on the flight from Maryland to Massachusetts, you should book around 3 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Maryland, there are direct flights to Massachusetts from 1 city. This city is Baltimore and there are 116 direct flights each week.

  • How many direct flights to Massachusetts are there each day?

    There are around 17 direct flights from within Maryland to Massachusetts every day. Most flights (38%) depart in the morning.

  • How many direct flights to Massachusetts are there each week?

    Each week there are around 116 direct flights from within Maryland to Massachusetts. The most common day for departures is Sunday, with 19% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Maryland to Massachusetts takes 6h 07m, covering a distance of 343 miles. The shortest route is Baltimore (BWI) to Hartford (BDL) with an average flight time of 1h 15m.

  • How many long-haul flights are there to Massachusetts each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Massachusetts. Instead, there are 116 short-haul flights (up to 3 hour flight duration), with the most arriving from Baltimore.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (86% of total searches to Massachusetts). The next most popular destinations are Albany (7%) and West Tisbury (4%). Searches for flights to Nantucket (3%), to Hyannis (1%) and to Worcester (0%) are also popular.

Reviews of the top 5 airlines serving from Maryland to Massachusetts

 
Need help choosing which airline to fly with from Maryland 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 4314 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

The AC broke and we were onboard for 2 hrs waiting for them to fix it. It was so hot and we could not get any water or anything to drink. They finally let us off the plane after the second attempt and we boarded a new plane. We didn't land till 12:15am!

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

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.

Bad. I know TSA is a mess right now but they “overbooked” the flight and almost didn’t let 10 of us on. Can’t put even a normal backpack under the seat, tray table is barely a foot wide, have to pay for literally everything. Apparently you can bid on your seats, too, so really the baseline ticket only covers the possibility of maybe getting on the plane. The staff were nice though, can only imagine the stress they are under.

Customer service online / on the phone are horrible. Flight crew is great but gate agents and customer service are terrible

We flew Spirit because it was cheaper but the seats were so uncomfortable. I don;t need to be fed snacks on a plane but when it's a 3-4 hour trip then at least a drink is nice. The flight attendants had nothing to do the whole flight except for gossip loudly to each other right behind our seats, and they talked so much my husband couldn't even rest! I was fine with no tv or entertainment but the seats were so uncomfortable with no recline, no padding, and I am short but even for me to leg room was tough for a 3-4 hour trip. We probably would fly spirit again if we had to, but it's definitely not our favorite!

The flight itself and the crew were great. Sitting on the tarmac for over an hour until our gate opened up was really frustrating. Missed our scheduled bus and got home two hours later

We sat on the tarmac for an hour and a half after landing.

Got surprised by passing an additional fee when selecting seats. No snack or drink offered. Will never use spirit again.

There absolutely needs to be WiFi on flights. Not sure why this new aircraft did not have the capability, but it made for a very frustrating flight. I honestly would have paid twice as much for another airline to have WiFi as an option, especially as a mom with kids who have disabilities.

Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Maryland

Cabin classes available on flights to Maryland. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.