$160+ Cheap flights from Massachusetts
This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
BOS — STN
8 Nov — 15 Nov1
Find flights from Massachusetts within your budget
Find flights departing from Massachusetts that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 9 October 2026. In the last 7 days, Cheapflights users made a total of 7,457,451 searches
Fly to
Route
Depart
Return
Cheapest return flight
BostonToronto
BOS Boston Logan Intl - YYZ Toronto Pearson Intl
BOSYYZ
Boston Logan Intl
Wed 28/10
15:01-21:15
1 stop6h 14m
Toronto Pearson Intl
Wed 31/12
00:00-00:00
Nonstop0h 00m
$160
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 29/10
06:00-13:08
1 stop8h 08m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$160
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 5/12
09:05-14:53
1 stop6h 48m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$160
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 17/12
13:05-16:17
1 stop4h 12m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$160
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 1/12
13:05-18:26
1 stop6h 21m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$160
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 3/12
09:05-14:49
1 stop6h 44m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$160
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 26/11
17:20-23:20
1 stop7h 00m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$160
BostonToronto
BOS Boston Logan Intl - YYZ Toronto Pearson Intl
BOSYYZ
Boston Logan Intl
Thu 29/10
10:25-16:47
1 stop6h 22m
Toronto Pearson Intl
Wed 31/12
00:00-00:00
Nonstop0h 00m
$167
BostonToronto
BOS Boston Logan Intl - YYZ Toronto Pearson Intl
BOSYYZ
Boston Logan Intl
Sat 14/11
19:00-23:26
1 stop4h 26m
Toronto Pearson Intl
Wed 31/12
00:00-00:00
Nonstop0h 00m
$167
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 28/10
06:00-10:28
1 stop5h 28m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
$184
Showing 1-10 of 60 resultsSorted by cheapest first
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.
BOS-ORD
BOS-YYZ
BOS-LAX
BOS-MXP
BOS-EDI
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Travel insights for flights from Massachusetts
Get recent, data-driven insights about flights from Massachusetts including ideal travel times, pricing trends, and more.
USMA-STN
BOS-ORD
BOS-YYZ
BOS-LAX
BOS-MXP
What is the cheapest place to fly to from Massachusetts?
The cheapest city to fly to from Massachusetts is Grand Rapids Gerald R. Ford Intl, with prices starting at $66. Explore other affordable destinations below.
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Direct flights from USA
Book a direct flight from one of these other cities located in USA.
Popular international destinations from United States
The most popular international flight routes departing from United States 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 9 October 2026.
Fly from other United States cities
Popular Return 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 9 October 2026.
Popular flight searches
Check out other popular destinations found by fellow travellers 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 9 October 2026.
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How does Cheapflights help users find flights from Massachusetts?
Deals for flights from Massachusetts are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Massachusetts?
Cheapflights simply makes it quick and affordable to book flights from Massachusetts by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Massachusetts with no change fees?
Certainly. Search results for flights from Massachusetts shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Massachusetts become cheaper?
Yes, Cheapflights offers price alerts on flights from Massachusetts so you can book your travels when it’s right. The Price Alerts feature is available by clicking the bell icon next to the flight deals above and providing your email address.