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FromBostonFri–Sundirect1 adult
Cheap weekend flights from Boston
The cheapest weekend from Boston is Orlando, at $157 return. October is the cheapest month, and Cancún, Savannah and Buffalo turn up as the best fare most often.
20 weekends ahead62 destinations · 21 countries · checked
Prices move. This page is rebuilt daily and shows the cheapest trip per weekend. The board searches live and knows every airline on the route.
Search live from BostonWeekend flights from Boston: quick answers
How cheap is a weekend flight from Boston?
Right now the cheapest is $157 return to Orlando. Across the next six months, half of all weekends have a trip at $398 or less.
What is the cheapest month for a weekend trip from Boston?
October, where the best weekend fare is $157 return.
Where can you fly for a weekend from Boston?
62 destinations in 21 countries have direct Friday-to-Sunday round trips in the months ahead. Cancún, Savannah and Buffalo come up as the cheapest most often.
Do I need to take days off work?
Usually not: every trip on this page leaves on Friday and returns on Sunday, so the work week stays intact. An early Friday departure can still mean leaving work after lunch, so check the times on the card. For longer breaks, the live board has a Long weekends option that searches around public holidays.
How fresh are these prices?
This page was rebuilt on September 3, 2026 and refreshes daily. Fares are from Kiwi.com; the final price is always the one at checkout.