$60+ Cheap flights from Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
Find flights from Massachusetts within your budget
Fly to
Route
Depart
Return
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Sat 10/24
9:00 am-2:24 pm
1 stop5h 24m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Fri 10/16
6:00 am-10:44 am
1 stop4h 44m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Wed 10/14
6:40 pm-10:59 pm
1 stop4h 19m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Mon 10/5
6:00 am-7:56 am
Nonstop1h 56m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - IAD Washington, D.C. Dulles Intl
BOSIAD
Boston Logan Intl
Fri 10/16
5:45 am-7:20 am
Nonstop1h 35m
Washington, D.C. Dulles Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Sun 10/4
6:00 am-9:46 am
1 stop3h 46m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Fri 10/2
9:51 am-2:24 pm
1 stop4h 33m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Thu 10/29
12:00 pm-4:28 pm
1 stop4h 28m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
HartfordOrlando
BDL Hartford Bradley Intl - MCO Orlando
BDLMCO
Hartford Bradley Intl
Thu 10/15
7:05 pm-12:23 am
1 stop5h 18m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonWashington, D.C.
BOS Boston Logan Intl - DCA Washington, D.C. Reagan-National
BOSDCA
Boston Logan Intl
Sat 9/12
2:19 pm-3:59 pm
Nonstop1h 40m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
Best time to book a flight from Massachusetts
Have a flexible travel schedule? Discover the best time to fly from Massachusetts with our price prediction graph.
Travel insights for flights from Massachusetts
Get recent, data-driven insights about flights from Massachusetts including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Massachusetts (average of $196). Flying from Massachusetts in October will prove the most costly (average of $284). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
Which airlines fly from Massachusetts?
For flights departing from Massachusetts check dates and pricing for the following: United Airlines, American Airlines, Delta, JetBlue. These airlines depart to the following popular destinations: Chicago.
What is the cheapest place to fly to from Massachusetts?
The cheapest city to fly to from Massachusetts is Des Moines, with prices starting at $59. Explore other affordable destinations below.
When is the best time to book a flight from Massachusetts?
To ensure you get the cheapest price possible for a flight from Massachusetts, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
When is the cheapest time to fly from Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to O'Hare Intl. Price data was last updated on June 8, 2026.
Those who are seeking the cheapest fare on flights departing from Massachusetts would be wise to consider leaving during Friday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday at noon when fares are usually the most expensive.
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Popular international destinations from Massachusetts
The most popular international flight routes departing from Massachusetts we’ve come across at this time.
Fly from popular cities in Massachusetts
Consider departing from one of these cities also located in Massachusetts. Flight origins are based on user searches made on Cheapflights and were last updated on September 9, 2026.
Fly from other United States cities
Popular Round-Trip Flight Destinations
Consider these popular destinations that Cheapflights users have chosen when departing from Massachusetts. Routes are based on user searches and were last updated on September 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Related info for your journey
Access useful and relevant information related to your journey from Massachusetts. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated September 9, 2026.