$69 Find Cheap Flights from Massachusetts to Maryland

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Low seasonFebruary
Cheapest flight$69
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Boston to Philadelphia

FAQs for booking flights from Massachusetts to Maryland

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

    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 Massachusetts to Maryland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Massachusetts to Maryland 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 Massachusetts to Maryland?

    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 Massachusetts to Maryland 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 Massachusetts to Maryland?

    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 Massachusetts to Maryland 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 Maryland?

    Massachusetts and Maryland are connected by different airlines. The airlines that fly that route the most regularly are Southwest (40 flights per week), Delta (20 flights per week), and Korean Air (7 flights per week).

  • How many airports are there in Maryland?

    There are 3 airports in Maryland. The busiest airport is Baltimore/Washington Airport (BWI), with 98% of all flights arriving there.

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Maryland is Baltimore/Washington Airport (BWI), with an average flight price of $226.

  • What is the cheapest day to fly to Maryland?

    Based on KAYAK data, the cheapest day to fly to Maryland is Friday where round-trip tickets can be as cheap as $291. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $391 on average.

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

    The cheapest time of day to fly to Maryland is generally in the evening, when round-trip flights cost $303 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $376.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Massachusetts found in the last 72 hours was to Baltimore, at $141 round-trip. The most popular route is Boston (BOS) to Baltimore (BWI) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $141.

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

    The cheapest month for flights from Massachusetts to Maryland is June, when tickets cost $186 (return) on average. On the other hand, the most expensive months are November and October, when the average cost of round-trip tickets is $330 and $294 respectively.

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

    To get a below average price on the flight from Massachusetts to Maryland, you should book around 3 weeks before departure, which saves you about 37% 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 Maryland?

    From Massachusetts, there are direct flights to Maryland from 1 city. This city is Boston and there are 88 direct flights each week.

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

    There are around 13 direct flights from within Massachusetts to Maryland every day. Most flights (53%) depart in the afternoon.

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

    Each week there are around 88 direct flights from within Massachusetts to Maryland. The most common day for departures is Thursday, with 16% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Massachusetts to Maryland takes 5h 04m, covering a distance of 335 miles. The shortest route is Hartford (BDL) to Baltimore (BWI) with an average flight time of 1h 20m.

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

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Maryland. Instead, there are 88 short-haul flights (up to 3 hour flight duration), with the most arriving from Boston.

  • What are the most popular destinations in Maryland?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (88% of total searches to Maryland). The next most popular destinations are Philadelphia (12%) and Salisbury (0%).

Reviews of the top 5 airlines serving from Massachusetts to Maryland

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

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

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.

We had a 5 hour delay on the tarmac in Baltimore

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

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

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.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

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

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

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.

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.

The bag situation was confusing. I didn’t know I had to pay for Carry ons. The seats were uncomfortable and there was no entertainment

4 hour delay, 2 hours in the airport and then 2 hours on the tarmac. With a flight full of kids it would have been better to leave us in the airport for the delay, it was crying kids chaos on the flight. Miserable. And no apology or airline credit for the significant delay.

They charged late fees for selecting seats (no $0 options). They also changed my gate within the last half hour and are refusing to reimburse my costs to drive across the country with two small children in a rental car.

The flight itself was great except for an air traffic controller delay. We left 30 min late but they made up most of the time in flight. The booking was frustrating, as we chose a certain flight and it was changed four times. We got to Orlando several hours later than the original flight we chose.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

Flight was cancelled with very little notice. Had to scramble to find transportation to my Mexico vacation.

Every Spirit flight we took was delayed by nearly 2 hours. We arrived in MCO and learned that our connection had been canceled. There were no options for rebooking for 4 days. No hotel vouchers provided, no transportation etc. The airline essentially stranded us, and rhe passengers from 6 other flights hours from our destinations with no assistance. Still no word on my refund. Terrible customer service.

AWFUL THEY CANCELED MY FLIGHT LESS THAN 12 HOURS BEFORE AND GAVE NO WAY TO GET A REFUND OR BOOK A NEW FLIGHT. THEN HAD THE AUDACITY TO GIVE ME A $30 VOUCHER ON A $500 FLIGHT

Everything you need to know for your flight to Maryland

Cabin class types available on flights to Massachusetts

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