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Find cheap Southwest flights to Boston from $68

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Flights Deals

Cheap Southwest Flight Deals to Boston

 
Here are some of the best deals found on KAYAK recently from Southwest 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.

Recent round-trip Southwest flight deals to Boston

KAYAK's recommended round-trip Southwest deals departing in the coming months to Boston.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
1:50 pm - 7:20 pmORD-BOS
4h 30m1 stop
Southwest Logo
6:50 am - 2:15 pmBOS-ORD
8h 25m1 stop
$136Southwest
Find Deal
Wed, Aug 27 - Sun, Aug 31
Southwest Logo
1:50 pm - 12:25 amORD-BOS
9h 35m1 stop
Southwest Logo
5:45 am - 11:50 amBOS-ORD
7h 05m1 stop
$142Southwest
Find Deal
Fri, Jun 6 - Tue, Jun 10
Southwest Logo
1:50 pm - 12:25 amORD-BOS
9h 35m1 stop
Southwest Logo
5:00 am - 12:45 pmBOS-ORD
8h 45m1 stop
$148Southwest
Find Deal
Fri, Jun 6 - Wed, Jun 11
Southwest Logo
6:35 am - 8:10 amBWI-BOS
1h 35mnonstop
Southwest Logo
7:55 pm - 9:30 pmBOS-BWI
1h 35mnonstop
$161Southwest
Find Deal
Wed, May 21 - Wed, May 21
Southwest Logo
6:20 am - 7:50 amBWI-BOS
1h 30mnonstop
Southwest Logo
9:45 pm - 11:20 pmBOS-BWI
1h 35mnonstop
$173Southwest
Find Deal
Thu, May 29 - Mon, Jun 2
Southwest Logo
1:50 pm - 7:10 pmORD-BOS
4h 20m1 stop
Southwest Logo
6:05 am - 11:50 amBOS-ORD
6h 45m1 stop
$186Southwest
Find Deal
Tue, May 13 - Tue, May 20
Southwest Logo
4:00 pm - 11:55 pmORD-BOS
6h 55m1 stop
Southwest Logo
5:50 am - 1:05 pmBOS-ORD
8h 15m1 stop
$192Southwest
Find Deal
Wed, Jun 25 - Mon, Jun 30
Southwest Logo
10:50 pm - 12:25 amBWI-BOS
1h 35mnonstop
Southwest Logo
5:15 am - 6:45 amBOS-BWI
1h 30mnonstop
$195Southwest
Find Deal
Fri, Jun 27 - Sun, Jun 29
Southwest Logo
1:50 pm - 10:45 pmORD-BOS
7h 55m1 stop
Southwest Logo
5:00 am - 12:45 pmBOS-ORD
8h 45m1 stop
$197Southwest
Find Deal
Fri, Jun 27 - Wed, Jul 2
Southwest Logo
1:50 pm - 12:25 amORD-BOS
9h 35m1 stop
Southwest Logo
5:00 am - 12:45 pmBOS-ORD
8h 45m1 stop
$198Southwest
Find Deal
Thu, Jul 3 - Tue, Jul 8
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Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$68
Average price round-trip$291
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago O'Hare Airport to Boston
(price for this month)

When to book flights with Southwest to Boston

Average price per month
Flight prices as travel date approaches

FAQs for flying to Boston with Southwest

  • Which other airlines fly to Boston?

    Along with Southwest, you can also fly to Boston with United Airlines, JetBlue, Cape Air, JetBlue, Allegiant Air, Allegiant Air, Hawaiian Airlines, United Airlines, Delta, Delta and American Airlines.

  • How much is a flight to Boston with Southwest?

    On average, Southwest flights to Boston cost $170 one-way.

  • Which airport do Southwest flights to Boston fly into?

    You’ll fly into Boston Logan Airport when flying to Boston with Southwest.

Top tips for your flights to Boston with Southwest

  • The cheapest flight to Boston with Southwest found on KAYAK in the last 2 weeks departed from Chicago Midway Airport and cost $48.

Southwest customer reviews

8.0
Very goodBased on 4,294 verified guest reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
K
8.0 Very good
Start drink service earlier. We were rushed.
J
8.0 Very good
It is southwest seat was ok. Not the most comfortable seat
H
6.0 Okay
They were more than 2 hours late.
H
10.0 Wonderful
Good
J
8.0 Very good
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
J
6.0 Okay
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
A
10.0 Wonderful
Plz don't take away free bags and free seating
D
6.0 Okay
The seats were a bit cramped and worn, but otherwise okay.
D
6.0 Okay
The seats were a bit cramped, but otherwise okay.
A
8.0 Very good
It departed late
Read more about Southwest

Everything you need to know for your flight to Boston

Other airlines flying to Boston

Flight deals from the most popular airlines with KAYAK users flying the route
Delta flights to Boston
American Airlines flights to Boston
United Airlines flights to Boston
Spirit Airlines flights to Boston
JetBlue flights to Boston

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