$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 (25 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 $227.

  • 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 $304 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 $373.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Massachusetts found in the last 72 hours was to Baltimore, at $133 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 $133.

  • 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 98 direct flights each week.

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

    There are around 14 direct flights from within Massachusetts to Maryland every day. Most flights (58%) depart in the afternoon.

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

    Each week there are around 98 direct flights from within Massachusetts to Maryland. The most common day for departures is Sunday, with 17% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Massachusetts to Maryland takes 6h 12m, covering a distance of 335 miles. The shortest route is Hartford (BDL) to Philadelphia (PHL) with an average flight time of 1h 17m.

  • 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 98 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. (84% of total searches to Maryland). The next most popular destinations are Philadelphia (16%) 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 4333 reviews
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

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.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

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

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

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

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.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

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

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

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.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

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.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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.