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$176+ Cheap flights from Boston

BOS — SYD
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find flights from Boston within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest return flight

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 10/12

16:35-18:45

Nonstop3h 10m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$176

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 19/12

05:45-07:51

Nonstop3h 06m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$205

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 23/12

05:30-09:49

1 stop5h 19m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$233

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 30/12

19:40-23:39

1 stop4h 59m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$233

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Fri 11/12

16:35-18:45

Nonstop3h 10m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$233

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 26/12

05:30-09:49

1 stop5h 19m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$233

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 2/12

14:00-20:45

1 stop7h 45m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$233

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Fri 27/11

13:35-15:33

Nonstop2h 58m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$253

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 10/11

07:30-09:35

Nonstop3h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$253
Fastest return journey

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 18/4

20:10-22:04

Nonstop2h 54m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

$253

Flights are sorted by cheapest return flights first.

Deals found on 29/10

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Boston

Have a flexible travel schedule? Discover the best time to fly from Boston with our price prediction graph.
Estimated return price

Travel insights for flights from Boston

Get recent, data-driven insights about flights from Boston including ideal travel times, pricing trends, and more.

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

Currently, May is the cheapest month in which you can book a flight from Boston (average of $1,790). Flying from Boston in December will prove the most costly (average of $2,638). 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 Boston?

When flying from Boston check dates and pricing for the following: Qantas Airways, United Airlines. As they depart for the following popular destinations: Sydney.

Qantas Airways
Qantas Airways
From $1,622
Air Canada
Air Canada
From $1,280
United Airlines
United Airlines
From $1,755

What are popular destinations to fly to from Boston?

Boston offers frequent flights to New York (860 flights per day), Chicago (275 flights per day) and Orlando (226 flights per day).

Los Angeles
Los Angeles
From $269
San Francisco
San Francisco
From $274
Simpson Bay Princess Juliana
Simpson Bay Princess Juliana
From $279
Edinburgh Turnhouse
Edinburgh Turnhouse
From $769

What is the cheapest place to fly to from Boston?

The cheapest city to fly to from Boston is Grand Rapids Gerald R. Ford Intl, with prices starting at $65. Explore other affordable destinations below.

Grand Rapids Gerald R. Ford Intl
Grand Rapids Gerald R. Ford Intl
From $65
Syracuse Hancock Intl
Syracuse Hancock Intl
From $164
Los Angeles
Los Angeles
From $269
San Francisco
San Francisco
From $274

When is the best time to book a flight from Boston?

The best time to book flights from Boston is 1 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Airline reviews for flights from Boston

Get a feel of what it's like to fly with Qantas Airways and United Airlines from Boston by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
1,121 reviews
Check prices

Overall

7.5

Food

7.0

Crew

8.1

Comfort

7.5

Boarding

7.7

Entertainment

7.2

Reviews

1 / 20
4.0
Okay

Robyn,Aug 2026

LAX - SYD

I was flabbergasted when the crew completely missed me in the distribution of food and drinks in Business Class - even after they looked twice at my opened table. However - this has happened to me on my last longhaul QF flight and with the same hosty (older woman with curly bob). She obviously cannot handly the stress of initial boarding as both times she has come back to me with an apology. When compared to our usual Business/ First longhauls with Qatar or Emirates, Qantas leave ALOT to be desired. I would highly recommend going with another airline. BTW I'm a 4th gen Aussie and previous Qantas employee - I would love to love them if they provided service but they just dont.
Qantas Airways
7.5
Good
1,121 reviews
Qantas Airways
7.5
Good
1,121 reviews
Check prices

Overall

7.5

Food

7.0

Crew

8.1

Comfort

7.5

Boarding

7.7

Entertainment

7.2

Reviews

1 / 20
4.0
Okay

Robyn,Aug 2026

LAX - SYD

I was flabbergasted when the crew completely missed me in the distribution of food and drinks in Business Class - even after they looked twice at my opened table. However - this has happened to me on my last longhaul QF flight and with the same hosty (older woman with curly bob). She obviously cannot handly the stress of initial boarding as both times she has come back to me with an apology. When compared to our usual Business/ First longhauls with Qatar or Emirates, Qantas leave ALOT to be desired. I would highly recommend going with another airline. BTW I'm a 4th gen Aussie and previous Qantas employee - I would love to love them if they provided service but they just dont.
United Airlines
7.3
Good
10,449 reviews
Qantas Airways
7.5
Good
1,121 reviews
Check prices

Overall

7.5

Food

7.0

Crew

8.1

Comfort

7.5

Boarding

7.7

Entertainment

7.2

Reviews

1 / 20
4.0
Okay

Robyn,Aug 2026

LAX - SYD

I was flabbergasted when the crew completely missed me in the distribution of food and drinks in Business Class - even after they looked twice at my opened table. However - this has happened to me on my last longhaul QF flight and with the same hosty (older woman with curly bob). She obviously cannot handly the stress of initial boarding as both times she has come back to me with an apology. When compared to our usual Business/ First longhauls with Qatar or Emirates, Qantas leave ALOT to be desired. I would highly recommend going with another airline. BTW I'm a 4th gen Aussie and previous Qantas employee - I would love to love them if they provided service but they just dont.

Browse thousands of different options on Cheapflights for your next trip

Related info for your journey

  • What are the most popular destinations to fly to from Boston?

    For the current month, the most popular flights from Boston are Nashville, Atlanta, Barcelona-El Prat Airport. Atlanta, Mumbai, Oranjestad are the most popular locations from Boston year round.

  • What is the cheapest flight from Boston to anywhere?

    Users have flown out of Boston for as low as $65 to Grand Rapids (prices may vary depending on the airline and departure time). On average, users have booked flights for $1,229 to fly from Boston.

  • What are the cheapest airlines flying from Boston to anywhere?

    According to our data, users have found Air Canada, Qantas Airways, and United Airlines to have the cheapest round-trip prices from Boston. Some of the destinations and prices are as follows: Air Canada flights from Boston to Brisbane ($1,280). Qantas Airways flights from Boston to Sydney Kingsford Smith ($1,622). United Airlines flights from Boston to Sydney Kingsford Smith ($1,755).

  • What is the cheapest premium economy flight from Boston?

    Options for some of the cheapest premium economy flights from Boston we have found on Cheapflights are as follows:
    Fly from Boston Logan Intl to Philadelphia starting at $1,696
    Fly from Boston Logan Intl to San Francisco starting at $5,026
    Fly from Boston Logan Intl to London Heathrow Airport starting at $6,575

  • What is the cheapest month to fly from Boston?

    Currently, the cheapest month for flights from Boston is May. The most expensive month for flights is December. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

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

    View the cheapest flight destinations from Boston:
    Fly from Boston to London from $494 round trip
    Fly from Boston to Sydney from $1,632 round trip
    Fly from Boston to Melbourne from $1,672 round trip

  • How does Cheapflights help users find flights from Boston?

    Cheapflights makes it easy to find flights from Boston by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

  • Why should you use Cheapflights to find cheap flight tickets from Boston?

    Cheapflights simply makes it quick and affordable to book flights from Boston 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 Boston with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Boston become cheaper?

    Not ready to book yet? You can track prices for flights from Boston on Cheapflights with our Price Alerts feature and get notified when better prices are available.

See more FAQs

Fly with Cheapflights

How does Cheapflights help users find flights from Boston?

Cheapflights makes it easy to find flights from Boston by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Boston?

Cheapflights simply makes it quick and affordable to book flights from Boston 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 Boston with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Boston become cheaper?

Not ready to book yet? You can track prices for flights from Boston on Cheapflights with our Price Alerts feature and get notified when better prices are available.

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