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Massachusetts

$73+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SEA
Jun 25 — Jul 21
Thu 6/25
Thu 7/2
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 May 26, 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

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 8/22

7:35 pm-10:54 pm

Nonstop3h 19m

Orlando

Sat 8/29

7:00 am-10:10 am

Nonstop3h 10m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/28

8:15 pm-10:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 8/4

1:55 pm-5:31 pm

Nonstop2h 36m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/14

4:15 pm-6:19 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sat 7/18

4:30 pm-8:11 pm

Nonstop2h 41m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/13

11:05 am-1:00 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 6/17

8:20 pm-11:51 pm

Nonstop2h 31m

$205

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/9

8:15 pm-10:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Fri 7/10

1:55 pm-5:31 pm

Nonstop2h 36m

$205

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/23

8:15 pm-10:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 7/28

6:00 am-11:16 am

1 stop4h 16m

$211

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/20

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 8/22

8:00 pm-11:35 pm

Nonstop2h 35m

$211

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/14

5:45 am-9:36 am

1 stop4h 51m

Chicago O'Hare Intl

Mon 7/20

9:41 pm-1:14 am

Nonstop2h 33m

$215

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 6/15

8:20 pm-10:20 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 6/17

6:00 am-11:16 am

1 stop4h 16m

$215

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/31

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 8/3

9:41 pm-1:14 am

Nonstop2h 33m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/23

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 $1,379). 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, Hawaiian Airlines. These airlines depart to the following popular destinations: Seattle.

JetBlue
JetBlue
From $68
Delta
Delta
From $58
American Airlines
American Airlines
From $107
United Airlines
United Airlines
From $84

What is the cheapest place to fly to from Massachusetts?

The cheapest city to fly to from Massachusetts is Fort Lauderdale, with prices starting at $43. Explore other affordable destinations below.

Fort Lauderdale
Fort Lauderdale
From $43
Presque Isle
Presque Isle
From $43
Des Moines
Des Moines
From $53
Asheville Regional
Asheville Regional
From $57

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 48 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 May 26, 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 Valparaiso from $77 round trip
    Fly from Boston to Sarasota from $111 round trip
    Fly from Boston to Syracuse from $114 round trip
    Fly from Boston to Washington, D.C. from $127 round trip
    Fly from Boston to Knoxville from $131 round trip

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