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Massachusetts

$96+ Cheap flights from Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SEA
Aug 10 — Aug 171
Mon 8/10
Mon 8/17
1 adult, Economy
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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 July 11, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/25

8:15 am-10:12 am

Nonstop2h 57m

Chicago O'Hare Intl

Tue 8/4

7:45 pm-11:21 pm

Nonstop2h 36m

$166

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/8

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Wed 9/9

6:10 am-9:33 am

Nonstop2h 23m

$168

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/8

7:30 am-9:24 am

Nonstop2h 54m

Chicago O'Hare Intl

Thu 9/17

7:35 am-11:08 am

Nonstop2h 33m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/4

8:05 am-10:04 am

Nonstop2h 59m

Chicago O'Hare Intl

Fri 9/4

7:59 pm-11:34 pm

Nonstop2h 35m

$170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/22

11:05 am-12:59 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 8/24

9:40 am-6:27 pm

1 stop7h 47m

$171

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/7

5:01 am-8:48 am

1 stop4h 47m

Chicago O'Hare Intl

Tue 9/15

8:24 pm-11:58 pm

Nonstop2h 34m

$171

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 9/16

1:05 pm-10:05 pm

1 stop9h 00m

Orlando

Tue 9/22

10:20 am-4:10 pm

1 stop5h 50m

$183
Quickest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/5

6:42 pm-8:40 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 9/7

6:15 am-9:36 am

Nonstop2h 21m

$183

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 12/15

11:20 am-8:00 pm

2 stops8h 40m

Orlando

Wed 12/16

2:30 pm-7:00 pm

1 stop4h 30m

$184

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/20

5:21 pm-7:27 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 8/23

8:20 pm-11:51 pm

Nonstop2h 31m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/9

Showing 1-10 of 60 resultsSorted by cheapest first
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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.
Estimated round-trip 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.

What is the cheapest month to book a flight from Massachusetts?

Currently, March is the cheapest month in which you can book a flight from Massachusetts (average of $108). Flying from Massachusetts in December will prove the most costly (average of $1,317). 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: Delta, Alaska Airlines, JetBlue, American Airlines, United Airlines. These airlines depart to the following popular destinations: Seattle.

Ethiopian Air
Ethiopian Air
From $828
ASKY
ASKY
From $451
Kenya Airways
Kenya Airways
From $327
Air Peace
Air Peace
From $233

What is the cheapest place to fly to from Massachusetts?

The cheapest city to fly to from Massachusetts is Presque Isle, with prices starting at $52. Explore other affordable destinations below.

Presque Isle
Presque Isle
From $52
Massena Richards Field
Massena Richards Field
From $55
Nantucket Memorial
Nantucket Memorial
From $58
Rutland
Rutland
From $67

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 63 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.

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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 July 11, 2026.

  • What is the cheapest month to fly from Massachusetts?

    March is currently the cheapest month to fly from Massachusetts. At this moment in time December is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Massachusetts?

    Check out the cheapest flights from Massachusetts to embark to:
    Fly from Boston to Orlando from $84 round trip
    Fly from Boston to Sarasota from $85 round trip
    Fly from Boston to Des Moines from $85 round trip
    Fly from Boston to Fort Lauderdale from $86 round trip
    Fly from Boston to Knoxville from $87 round trip

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