Cheap flights from Cleveland to Boston from $104

In general, January is the cheapest month to fly from Cleveland to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $158. If you aren’t able to travel during the month of January, then book flights to Boston from Cleveland during September instead. Flights to Boston in September, while not as cheap as those in January, still average around $177.

The cheapest day to depart from Cleveland to Boston is on a Friday when prices can be found for as low as $249. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $451.

According to our data, the cheapest time of day to fly to Boston is in the morning. momondo users have found flights departing from Cleveland to Boston in the morning for as low as $273. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $596 per ticket.

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

You are more likely to see cheaper flights to Boston from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $225 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Cleveland for as low as $180 on momondo.

You could potentially save up to 14% on your flight if you consider stops on a Cleveland to Boston flight.

As of May 2026, prices for Cleveland to Boston flights are approximately 1% more expensive when compared to flights at the same time last year.

United Airlines and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Boston Logan Intl

JetBlue, Delta and Frontier are the top three most popular airlines that fly to Boston from Cleveland according to our data. JetBlue is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 8 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

The number of flights available between Cleveland and Boston is 11 per day as of May 2026. The most frequent departure time is 9:00AM, with 65% of daily flights leaving at noon.

The number of flights available between Cleveland and Boston is 81 per week as of May 2026. The most frequent departure day is Fri, with 23% of weekly flights leaving on this day.