Rp 1,985,689+ 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 29/10. 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 — DPS
9 Nov — 16 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 10 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
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 19/11
14.00-19.25
1 stop6h 25m
Chicago O'Hare Intl
Wed 31/12
00.00-01.00
Nonstop0h 00m
Rp 1,985,689
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 12/11
09.15-13.59
1 stop5h 44m
Chicago O'Hare Intl
Wed 31/12
00.00-01.00
Nonstop0h 00m
Rp 1,985,689
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
Rp 1,985,689
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
Rp 1,985,689
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
Rp 1,985,689
BostonNewark
BOS Boston Logan Intl - EWR Newark
BOSEWR
Boston Logan Intl
Tue 1/12
12.00-13.28
Nonstop1h 28m
Newark
Wed 31/12
00.00-00.00
Nonstop0h 00m
Rp 2,218,247
BostonNewark
BOS Boston Logan Intl - EWR Newark
BOSEWR
Boston Logan Intl
Tue 8/12
06.25-08.04
Nonstop1h 39m
Newark
Wed 31/12
00.00-00.00
Nonstop0h 00m
Rp 2,218,247
BostonNewark
BOS Boston Logan Intl - EWR Newark
BOSEWR
Boston Logan Intl
Wed 16/12
06.25-08.04
Nonstop1h 39m
Newark
Wed 31/12
00.00-00.00
Nonstop0h 00m
Rp 2,218,247
BostonNewark
BOS Boston Logan Intl - EWR Newark
BOSEWR
Boston Logan Intl
Wed 11/11
06.25-08.00
Nonstop1h 35m
Newark
Wed 31/12
00.00-00.00
Nonstop0h 00m
Rp 2,218,247
BostonMiami
BOS Boston Logan Intl - MIA Miami
BOSMIA
Boston Logan Intl
Sun 6/12
09.15-18.50
1 stop9h 35m
Miami
Wed 31/12
00.00-00.00
Nonstop0h 00m
Rp 2,325,582
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-AUS
BOS-MIA
BOS-PIT
BOS-ORD
BOS-EWR
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-DPS
BOS-AUS
BOS-MIA
BOS-PIT
BOS-ORD
What is the cheapest month to book a flight from Massachusetts?
Currently, February is the cheapest month in which you can book a flight from Massachusetts (average of Rp 20,500,894). Flying from Massachusetts in December will prove the most costly (average of Rp 37,889,088). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
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 45 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.
Browse thousands of different options on Cheapflights for your next trip
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Direct flights from USA
Other Massachusetts origins
Other United States cities
Popular flights
Direct flights from USA
Book a direct flight from one of these other cities located in USA.
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 10 October 2026.
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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 10 October 2026.
Fly with Cheapflights
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How does Cheapflights help users find flights from Massachusetts?
Cheapflights helps you search for flights from Massachusetts via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
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.