$108 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$210
Albany
Albany1 stop$277
Boston
Boston1 stop$210
Albany
Albany1 stop$277
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 $202 and $364 in October.
The lowest price found in the past 5 days was $210 on Frontier (Oct 17-Oct 21).

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 $193 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 $193.

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 $279 on average. Morning departures are around 45% 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 $618.

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

No, with an average price for the route of $342, prices are generally cheapest when you fly direct.

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 June and July, when the average cost of round-trip tickets is $338 and $321 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, Tuesday is the most expensive day to fly from Cleveland to Massachusetts. For your return ticket, we recommend flying on a Friday and avoiding Mondays 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 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

January

Cheapest flight

$108
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Cleveland to Hartford

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 $199 one-way - $297 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 8505 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.8Comfort
7.2Food
Airline reviews

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.

4.0 OkayNoel, Aug 2026
Read more Delta reviews

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.

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

The tray table was broken and the food was terrible.

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

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.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

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.

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.

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

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

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

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

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.

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

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