$64+ 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 10/30. 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
BostonFort Lauderdale
BOS Boston Logan Intl - FLL Fort Lauderdale
BOSFLL
Boston Logan Intl
Tue 10/20
6:45 am-2:50 pm
2 stops8h 05m
Fort Lauderdale
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 10/22
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 11/27
7:15 am-12:29 pm
1 stop5h 14m
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
Sat 10/17
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
BostonFort Lauderdale
BOS Boston Logan Intl - FLL Fort Lauderdale
BOSFLL
Boston Logan Intl
Wed 12/2
2:45 pm-9:51 pm
1 stop7h 06m
Fort Lauderdale
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 11/18
10:45 am-12:40 pm
Nonstop1h 55m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonFort Lauderdale
BOS Boston Logan Intl - FLL Fort Lauderdale
BOSFLL
Boston Logan Intl
Wed 12/9
2:35 pm-8:35 pm
1 stop6h 00m
Fort Lauderdale
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 10/19
9:51 am-3:24 pm
1 stop5h 33m
Washington, D.C. Reagan-National
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 10/17
6:00 am-10:53 am
1 stop5h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Sat 10/17
3:40 pm-6:54 pm
Nonstop3h 14m
Orlando
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 $243). Flying from Massachusetts in April will prove the most costly (average of $387). 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: JetBlue, Delta, American Airlines, Frontier, Southwest. These airlines depart to the following popular destinations: Orlando.
What is the cheapest place to fly to from Massachusetts?
The cheapest city to fly to from Massachusetts is Knoxville McGhee Tyson, with prices starting at $57. 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 23 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 Orlando. Price data was last updated on September 19, 2026.
Those who are seeking the cheapest fare on flights departing from Massachusetts would be wise to consider leaving during Sunday afternoons 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 26, 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 26, 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 26, 2026.