How far in advance should I book tickets for a flight with Southwest from Washington, D.C. to Boston?

Generally, when trying to get a below average price for your ticket, try to book around 14 days before departure. For the cheapest possible price, our data suggests booking 43 days before departure.

What is the cheapest Southwest flight from Washington, D.C. to Boston?

In the last 3 days, the lowest price for a flight with Southwest from Washington, D.C. to Boston was $111 for a return flight and $65 for a one-way flight.

Does Southwest fly direct to Boston from Washington, D.C.?

No, Southwest does not fly the route directly.

What’s the cheapest day of the week to fly from Washington, D.C. to Boston with Southwest?

On average, the cheapest day of the week to fly from Washington, D.C. to Boston with Southwest is Tuesday, when prices are around $73. The most expensive day is generally Thursday, where the average price is around $109.

What’s the cheapest month to fly from Washington, D.C. to Boston with Southwest?

The cheapest month for Southwest flights to Boston from Washington, D.C. is generally May, where plane tickets cost $127 on average. If possible, try to avoid the most expensive months of October and September, where tickets cost $274 and $426 respectively.

$96 Cheap Southwest Flights from Washington, D.C. to Boston

Flight Deals

Cheap Southwest Flight Deals from Washington, D.C. to Boston

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Washington, D.C. to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Washington, D.C. to Boston

Mon, Dec 8 - Tue, Dec 9

7:35 pm - 9:05 pmBWI-BOS

1h 30mnonstop

5:45 am - 7:25 amBOS-BWI

1h 40mnonstop

$191Southwest

Find Deal

Sat, Dec 6 - Mon, Dec 8

6:00 pm - 7:35 pmBWI-BOS

1h 35mnonstop

5:45 am - 7:25 amBOS-BWI

1h 40mnonstop

$203Southwest

Find Deal

Thu, Dec 4 - Sun, Dec 7

5:45 pm - 7:20 pmBWI-BOS

1h 35mnonstop

8:50 am - 10:30 amBOS-BWI

1h 40mnonstop

$214Southwest

Find Deal

Thu, Nov 27 - Tue, Dec 2

10:35 am - 12:05 pmBWI-BOS

1h 30mnonstop

5:35 pm - 7:20 pmBOS-BWI

1h 45mnonstop

$217Southwest

Find Deal

Wed, Nov 26 - Wed, Dec 3

9:10 pm - 10:40 pmBWI-BOS

1h 30mnonstop

5:45 am - 7:25 amBOS-BWI

1h 40mnonstop

$222Southwest

Find Deal

Fri, Nov 21 - Tue, Dec 2

6:35 am - 8:05 amBWI-BOS

1h 30mnonstop

7:45 am - 9:25 amBOS-BWI

1h 40mnonstop

$225Southwest

Find Deal

Sat, Dec 13 - Sat, Dec 20

6:35 am - 8:05 amBWI-BOS

1h 30mnonstop

7:45 am - 9:25 amBOS-BWI

1h 40mnonstop

$226Southwest

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:45 am - 8:15 amBWI-BOS

1h 30mnonstop

8:50 am - 10:30 amBOS-BWI

1h 40mnonstop

$232Southwest

Find Deal

Mon, Dec 22 - Sun, Dec 28

4:45 pm - 6:15 pmBWI-BOS

1h 30mnonstop

5:35 am - 7:15 amBOS-BWI

1h 40mnonstop

$234Southwest

Find Deal

Tue, Nov 25 - Tue, Dec 2

6:40 pm - 8:10 pmBWI-BOS

1h 30mnonstop

5:35 pm - 7:20 pmBOS-BWI

1h 45mnonstop

$235Southwest

Find Deal

Useful Info

Low season	February
High season	October
Cheapest flight	$96
Average price round-trip	$261

Best time to beat the crowds with an average 18% drop in price.

Most popular time to fly with an average 20% increase in price.

Flight from Baltimore to Boston

(price for this month)

When to Book Flights with Southwest from Washington, D.C. to Boston

Average price per month

Flight prices as travel date approaches

How far in advance should I book tickets for a flight with Southwest from Washington, D.C. to Boston?
Generally, when trying to get a below average price for your ticket, try to book around 14 days before departure. For the cheapest possible price, our data suggests booking 43 days before departure.
What is the cheapest Southwest flight from Washington, D.C. to Boston?
In the last 3 days, the lowest price for a flight with Southwest from Washington, D.C. to Boston was $111 for a return flight and $65 for a one-way flight.
Does Southwest fly direct to Boston from Washington, D.C.?
No, Southwest does not fly the route directly.
What’s the cheapest day of the week to fly from Washington, D.C. to Boston with Southwest?
On average, the cheapest day of the week to fly from Washington, D.C. to Boston with Southwest is Tuesday, when prices are around $73. The most expensive day is generally Thursday, where the average price is around $109.
What’s the cheapest month to fly from Washington, D.C. to Boston with Southwest?
The cheapest month for Southwest flights to Boston from Washington, D.C. is generally May, where plane tickets cost $127 on average. If possible, try to avoid the most expensive months of October and September, where tickets cost $274 and $426 respectively.

8.0

Very good4,240 verified ratings

8.0Comfort

8.1Boarding

8.6Crew

7.0Food

7.5Entertainment

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Cons -

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8.0 Very good

Margaret, Oct 2025

SAV-HOU

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 Very good

TODD, Oct 2025

CMH-HOU

Tried watching free movie and it kept freezing so I couldn’t finish.

10.0 Wonderful

Antonio, Oct 2025

PVD-MCO

Always reliable

10.0 Wonderful

Verified traveler, Oct 2025

MDW-BWI

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

4.0 Mediocre

Mike, Oct 2025

GRR-MDW

Staff/crew very good. 4 hour delay not good.

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

8.0 Very good

Verified traveler, Oct 2025

MHT-MDW

Getting worse with new changes.

4.0 Mediocre

Jeff, Oct 2025

MCI-SAN

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Everything you need to know for your flight from Washington, D.C. to Boston

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$96 Find Cheap Southwest Flights from Washington, D.C. to Boston

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Cheap Southwest Flight Deals from Washington, D.C. to Boston

Recent round-trip Southwest flight deals from Washington, D.C. to Boston

Recent one-way Southwest flight deals from Washington, D.C. to Boston

Recent last minute Southwest flight deals from Washington, D.C. to Boston

Recent direct Southwest flight deals from Washington, D.C. to Boston

Good to know

When to Book Flights with Southwest from Washington, D.C. to Boston

FAQs for flying to Boston with Southwest

How far in advance should I book tickets for a flight with Southwest from Washington, D.C. to Boston?

What is the cheapest Southwest flight from Washington, D.C. to Boston?

Does Southwest fly direct to Boston from Washington, D.C.?

What’s the cheapest day of the week to fly from Washington, D.C. to Boston with Southwest?

What’s the cheapest month to fly from Washington, D.C. to Boston with Southwest?

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Everything you need to know for your flight from Washington, D.C. to Boston

Other airlines flying from Washington, D.C. to Boston

Flight deals from the most popular airlines with KAYAK users flying the route

Cabin class types available on flights to Boston

Cabin classes available on flights to Washington, D.C.. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Boston with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.