Cheap flights from Cleveland to Massachusetts from $95

In general, January is the cheapest month to fly from Cleveland to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $159. If you aren’t able to travel to Massachusetts during the month of January, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $197.

According to our data, Friday is the cheapest day to fly to Massachusetts from Cleveland. The lowest ticket price found for a Friday departure recently was $261. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Cleveland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $450.

Our data shows that the cheapest Cleveland to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $277. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $610 on average. Flights to Massachusetts from Cleveland at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Cleveland Hopkins Intl to Boston Logan Intl for the best Cleveland Hopkins Intl - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $247 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Cleveland for as low as $210 on momondo.

There are 4 cabin classes available to choose from on Cleveland to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, JetBlue, and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Massachusetts

JetBlue, Delta and Frontier are the top three most popular airlines that fly to Massachusetts from Cleveland according to our data. JetBlue is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 5 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of August 2026, 14 flights take off from Cleveland and land in Massachusetts each day. The most common flight departure time for this route is 4:00PM, with 58% of daily flights taking off at noon.

As of August 2026, 103 flights take off from Cleveland and land in Massachusetts each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.