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Massachusetts

$59+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MIA
พ.ค. 9 — พ.ค. 161
ส. 5/9
ส. 5/16
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 เมษายน 9, 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

BostonFort Lauderdale

BOS - FLL

BOSFLL

Boston Logan Intl

ส. 4/25

8:16 pm-11:41 pm

Nonstop3h 25m

Fort Lauderdale

ส. 5/2

6:40 am-5:33 pm

1 stop10h 53m

$138

BostonFort Lauderdale

BOS - FLL

BOSFLL

Boston Logan Intl

จ. 8/24

5:30 am-9:03 am

Nonstop3h 33m

Fort Lauderdale

พ. 8/26

8:57 pm-8:20 am

1 stop11h 23m

$158
Quickest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

ศ. 5/8

7:30 am-9:30 am

Nonstop3h 00m

Chicago O'Hare Intl

อา. 5/10

7:30 am-11:01 am

Nonstop2h 31m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

พฤ. 6/18

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

พฤ. 6/18

9:26 pm-12:59 am

Nonstop2h 33m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

พ. 5/13

12:30 pm-2:30 pm

Nonstop3h 00m

Chicago O'Hare Intl

อา. 5/24

6:00 am-11:16 am

1 stop4h 16m

$182

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

พ. 5/20

8:00 am-1:47 pm

1 stop6h 47m

Chicago O'Hare Intl

อา. 5/24

7:00 am-10:35 am

Nonstop2h 35m

$186

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

พฤ. 5/7

5:45 am-9:37 am

1 stop4h 52m

Chicago O'Hare Intl

จ. 5/11

6:00 am-9:25 am

Nonstop2h 25m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

อ. 5/12

11:40 am-9:55 pm

2 stops11h 15m

Chicago O'Hare Intl

จ. 5/18

2:00 pm-8:15 am

2 stops17h 15m

$194

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

อา. 5/17

7:00 am-10:15 am

Nonstop3h 15m

Orlando

ส. 5/30

7:54 pm-11:04 pm

Nonstop3h 10m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

อา. 5/17

5:30 am-4:05 pm

2 stops11h 35m

Chicago O'Hare Intl

อ. 5/19

2:40 pm-10:30 pm

1 stop6h 50m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/7

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, August is the cheapest month in which you can book a flight from Massachusetts (average of $57). Flying from Massachusetts in December will prove the most costly (average of $108). 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 cheapest time to fly from Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Miami. Price data was last updated on April 4, 2026.

Those who are seeking the cheapest fare on flights departing from Massachusetts would be wise to consider leaving during Wednesday evenings 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.

Which airlines fly from Massachusetts?

For flights departing from Massachusetts check dates and pricing for the following: American Airlines, Spirit Airlines, Delta, JetBlue, Frontier. These airlines depart to the following popular destinations: Miami.

Ethiopian Air
Ethiopian Air
From $559
ASKY
ASKY
From $451
Kenya Airways
Kenya Airways
From $380
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 $38. Explore other affordable destinations below.

Presque Isle
Presque Isle
From $38
Valparaiso Destin-Ft Walton Beach
Valparaiso Destin-Ft Walton Beach
From $43
Traverse City Cherry Capital
Traverse City Cherry Capital
From $52

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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 เมษายน 9, 2026.

  • What is the cheapest month to fly from Massachusetts?

    August 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 Baltimore from $72 round trip
    Fly from Boston to Valparaiso from $75 round trip
    Fly from Boston to Presque Isle from $76 round trip
    Fly from Boston to Des Moines from $77 round trip
    Fly from Boston to Orlando from $83 round trip

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