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Best Weekend Trips from Boston

Real short-haul destinations from Boston — 2.5h flight time or under — ranked by flight time, with real live fares. Not every destination from Boston fits a weekend; this page only shows the ones that do.

Real weekend-trip destinations

DestinationFlight timeFare
Montreal1h 15m€137
Philadelphia1h 15m€113
Washington1h 16m€91
Baltimore1h 25m€190
Toronto1h 35m€81
New York1h 50m€92
Chicago2h 20m€89
Atlanta2h 30m€87

Making the most of a weekend trip

  • Pack cabin baggage only where you can — it's usually enough for 2-3 nights and skips checked-bag fees.
  • A Friday evening or Saturday morning departure with a Sunday evening return is the classic weekend pattern.
  • Book accommodation close to the centre — a short trip loses real time to a long transfer each way.
  • Check each route's own page for a full fare calendar before settling on exact dates.
  • Have a backup destination from the list above — the cheapest option can shift by the time you book.

Continue planning your trip to Montreal

Same destination, real availability — no need to search again.

Flights to MontrealHotels in MontrealThings to do in MontrealRent a car

Continue planning your trip to Philadelphia

Same destination, real availability — no need to search again.

Flights to PhiladelphiaHotels in PhiladelphiaThings to do in PhiladelphiaRent a car

Continue planning your trip to Washington

Same destination, real availability — no need to search again.

Flights to WashingtonHotels in WashingtonThings to do in WashingtonRent a car

More from Boston

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FAQs — Weekend trips from Boston

Ottawa has the shortest real flight time from Boston among the routes we checked, at around 1h 5m.