$177 Find Cheap Flights from Cleveland to Massachusetts - Compare and Save

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Cheap Flights from Cleveland to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Boston
Boston1 stop$286
Nantucket
Nantucket1 stop$994
Albany
Albany1 stop$287
Boston
Boston1 stop$286
Nantucket
Nantucket1 stop$994
Albany
Albany1 stop$287
Booking Insights

KAYAK's insights & trends for Cleveland to Massachusetts flights

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

How much is a round-trip flight from Cleveland to Massachusetts?

Flight prices are typical for this route right now.

Flights to Massachusetts from Cleveland usually cost between $238 and $426 in October.
The lowest price found in the past 5 days was $286 on Frontier (Oct 23-Oct 25).

What is the cheapest Cleveland to Massachusetts flight route?

The cheapest ticket to Massachusetts from Cleveland found in the last 5 days was to Boston, at $308 round-trip. The most popular route is from Cleveland (CLE) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $308.

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 $287 on average. Morning departures are around 44% 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 $662.

Can I save money by flying with a layover from Cleveland to Massachusetts?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $460 on average.

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

The cheapest month for flights from Cleveland to Massachusetts is January, when tickets cost $159 (return) on average. On the other hand, the most expensive months are September and June, when the average cost of round-trip tickets is $358 and $339 respectively.

What’s the cheapest day of the week to fly from Cleveland to Massachusetts?

If your flying dates are flexible, you should consider flying to Massachusetts on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Cleveland to Massachusetts. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

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

To get a below average price on the flight from Cleveland to Massachusetts, you should book around 2 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low season

January

Cheapest flight

$177
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Cleveland to Boston

FAQs - booking Massachusetts flights

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

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

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

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Cleveland to the following destinations at these prices or less: Boston $276 one-way - $429 round-trip

Reviews of the top 5 airlines serving from Cleveland to Massachusetts

 
Need help choosing which airline to fly with from Cleveland 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.
7.8
DeltaOverall score based on 8628 reviews
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

Flight was delayed and not a lot of communication on why until we got on the plane.

6.0 GoodJennifer, Oct 2026
Read more Delta reviews

Flight was delayed and not a lot of communication on why until we got on the plane.

Horrible experience. Delta delayed the flight to 11pm which happens. Apparently the pilots were there but we were waiting for flight attendants to arrive from Detroit and they were delayed. They could have made arrangements but that’s fine. What was truly horrible was that at 10:50pm the pilot comes out and says the flight will be cancelled but hasn’t been cancelled yet in the system. It’s being cancelled because the pilots have timed out. As soon as that plane got delayed past 10:50pm delta knew it couldn’t fly. Yet they made us wait around for hours. When the flight finally got cancelled all the area hotels were booked and flights for the next day were unavailable until midday. All I wanted was to spend one day with my family before needing to fly abroad on another delta flight. That will be my last flight with them. I’ll take my 800k miles flown and annual spend to an airline that isn’t so thoughtless.

got ahead of the schedule, nothing else to like. crew management of boarding when overhead bag space was virtually gone in the midst of their priority zone 3 should have been better. but they absolutely did not care. ryanair crew is better than this!

The crew were very respectful. And also they were welcoming.they did help us locate our seats.i enjoyed.

Terrible. Waited on runway for 1+ hour after landing and then was brought to wrong terminal

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

Please stop those idiotic and unrelenting announcements, commercials and stupid credit card drivel. All together about 15 minutes of stupidness that annoys each passenger.

Flight was delayed 14 hours due to DC air show and weather. Missed connection to MUC.

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

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

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

I like flying first class, and United has a nice one

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

The flight from Cleveland to Newark was great. The connecting flight wasn’t so good.

Flight was not comfortable and crew was rude and not wanted to help, i would never choose united if there is alternate options . not cooperative with baby

Seat comfort is still an issue. Seats way too hard or lacking lumbar support. Entertainment system has lots of nice features like “Don’t wake me for meals”. The Bluetooth headphone pairing works well if you know how to make your pods available for pairing. While this trip I didn’t find any of the many many movies that interesting, there is plenty in there for all tastes. Crew were excellent. Captain was good about telling us how limg seat belt sign would be on while going around a storm system. Wi-Fi was quite good for only $8 bucks for mileage plus members. Be sure to load a credit card into your United app to pay for food or drinks.

They lost my luggage and have ruined first day of my vacation. Still don’t have it. I have nothing. I also paid for a seat I did not get. They changed both our seats with no notice. Will never fly this airline again.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

Flight was delayed 3 hours. No food on plane besides snacks

Nice plane, with TV, comfortable seats and leg room. Updated regularly on time changes

What's not to like? Value?definitely. Every JetBlue member was extremely friendly on this flight. Very very nice new-ish aircraft,plenty of room. GOOD coffee. Entertainment,I didn't need it,but I think its available. What to do better? Well,there's nothing we can do about the other people, unbelievable how some folks are operating. Just don't allow people to lug all their stuff onto the aircraft. 1 bag. That's it. Be easier for you too. I personally would enjoy more options in schedule. One flight in and out a day is warranted given the local,I understand, but the times are inconvenient. Again, I completely understand why it is that way,It would however be great to have different options.

Had to wait over an hour in line for a Jet Blue agent to appear at the the counter. Ended up a customer service agent from another airline lines helped to check us in, and boarding pass,

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

There was a screen but no earphones that could use the older input so I could listen to anything.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

It was a code share with Alaska - would have been great if I actually made it on the plane, claimed I didn’t have a ticket or a seat even thought I was checked in.

Plenty of overhead space but forced to check my carry-ons both legs

The flight from CLE to JFK was fantasti! Pilots and cre were informative and accommodating.

Everything was ok except that we had to de-ice the plane which took about 20 mins. I realize this is a safety issue, but it caused us to miss a connection in Charlotte by 15 mins which meant a four hour layover. I think the thing that bothered me was American Airlines knew we were only 15 mins late, so couldn’t they have waited for us? There were about 10 of us that had to take alternate planes. I remember recently waiting 15 to 20 mins for passengers connecting with flights we were on. Just wondering why they couldn’t do the same for ours.

Another American flight delay. Gate staff was gratuitously abusive of anyone expressing frustration. This will be my last American Airlines flight

Abysmal, getting delayed approximately 13 times, having to switch out a crew with another crew that timed out within an hour, and customer service representatives that abandoned the stranded travelers. Terrible service

Flight attendants used to be nice to people. And any flight over 5 hours should have some kind of food other than tiny pretzels and one drink comped.

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

There was extremely long wait times to check in my bags and pass through TSA. I almost missed my flights on several occasions.

On both our outgoing flight and our return flight, Frontier split up our seats. We were two adults and two small children, one an infant. Both flights were only about half full with full rows of empty seats. Yet, the airline split us up. No, we did not spend the extra $40 per person each way to purchase seat assignments ahead of time. But should we have to do this? If so, then the advertised ticket price was $40 off. What makes this even more egregious is that the plane was not full. So, there was no reason for Frontier to split up our group other than to extract an extra $320. A stewardess even had the nerve to tell me “if you want your family to sit together, I recommend that you purchase seat assignments next time.” On a half empty flight? Ridiculous. We will not be flying Frontier again.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

More options for your flight from Cleveland to Massachusetts

Complete your trip to Massachusetts with a hotel stay or car rental