Does Southwest fly direct to Chicago Midway Airport from Boston?

Yes, Southwest does offer direct flights for the route, with around 5 flights per week.

What’s the cheapest day of the week to fly from Boston to Chicago Midway Airport with Southwest?

On average, the cheapest day of the week to fly from Boston to Chicago Midway Airport with Southwest is Monday, when prices are around $50. The most expensive day is generally Sunday, where the average price is around $68.

What’s the cheapest month to fly from Boston to Chicago Midway Airport with Southwest?

The cheapest month for Southwest flights to Chicago Midway Airport from Boston is generally June, where plane tickets cost $68 on average. If possible, try to avoid the most expensive months of November and July, where tickets cost $203 and $213 respectively.

$64 Cheap Southwest Flights from Boston to Chicago Midway Airport

BOS - MDW

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Flight Deals

Cheap Southwest Flight Deals from Boston to Chicago Midway Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Boston to Chicago Midway Airport 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 Boston to Chicago Midway Airport

Tue, Dec 16 - Sun, Dec 21

5:30 am - 7:15 amBOS-MDW

2h 45mnonstop

5:30 am - 8:45 amMDW-BOS

2h 15mnonstop

$124Southwest

Find Deal

Sun, Nov 9 - Mon, Nov 10

5:15 am - 7:00 amBOS-MDW

2h 45mnonstop

9:35 am - 12:50 pmMDW-BOS

2h 15mnonstop

$127Southwest

Find Deal

Sun, Nov 9 - Mon, Nov 10

5:15 am - 7:00 amBOS-MDW

2h 45mnonstop

5:15 pm - 10:55 pmMDW-BOS

4h 40m1 stop

$137Southwest

Find Deal

Sat, Feb 7 - Mon, Feb 9

5:30 am - 7:20 amBOS-MDW

2h 50mnonstop

6:35 pm - 9:50 pmMDW-BOS

2h 15mnonstop

$141Southwest

Find Deal

Fri, Nov 21 - Mon, Nov 24

6:55 pm - 8:45 pmBOS-MDW

2h 50mnonstop

7:15 pm - 10:30 pmMDW-BOS

2h 15mnonstop

$142Southwest

Find Deal

Wed, Nov 12 - Sun, Nov 16

5:30 am - 7:15 amBOS-MDW

2h 45mnonstop

5:05 am - 3:45 pmMDW-BOS

9h 40m1 stop

$143Southwest

Find Deal

Mon, Nov 10 - Wed, Nov 12

5:35 am - 11:10 amBOS-MDW

6h 35m1 stop

12:55 pm - 7:20 pmMDW-BOS

5h 25m1 stop

$147Southwest

Find Deal

Sat, Feb 7 - Mon, Feb 9

5:45 am - 11:25 amBOS-MDW

6h 40m1 stop

6:35 pm - 9:50 pmMDW-BOS

2h 15mnonstop

$151Southwest

Find Deal

Fri, Nov 21 - Mon, Nov 24

6:55 pm - 8:45 pmBOS-MDW

2h 50mnonstop

5:00 am - 12:50 pmMDW-BOS

6h 50m1 stop

$152Southwest

Find Deal

Sat, Jan 24 - Fri, Jan 30

5:30 am - 7:20 amBOS-MDW

2h 50mnonstop

2:00 pm - 5:10 pmMDW-BOS

2h 10mnonstop

$154Southwest

Find Deal

Useful Info

Low season	February
High season	July
Cheapest flight	$64
Average price round-trip	$287
Good deal one-way	$198

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly and prices are also 1% lower on average.

Flight from Boston to Chicago Midway Airport

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Boston to Chicago Midway Airport

Average price per month

Flight prices as travel date approaches

What is the cheapest Southwest flight from Boston to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight with Southwest from Boston to Chicago Midway Airport was $117 for a return flight and $58 for a one-way flight.
Does Southwest fly direct to Chicago Midway Airport from Boston?
Yes, Southwest does offer direct flights for the route, with around 5 flights per week.
What’s the cheapest day of the week to fly from Boston to Chicago Midway Airport with Southwest?
On average, the cheapest day of the week to fly from Boston to Chicago Midway Airport with Southwest is Monday, when prices are around $50. The most expensive day is generally Sunday, where the average price is around $68.
What’s the cheapest month to fly from Boston to Chicago Midway Airport with Southwest?
The cheapest month for Southwest flights to Chicago Midway Airport from Boston is generally June, where plane tickets cost $68 on average. If possible, try to avoid the most expensive months of November and July, where tickets cost $203 and $213 respectively.

8.0

Very good4,243 verified ratings

8.1Boarding

7.5Entertainment

8.6Crew

8.0Comfort

7.0Food

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

James, Oct 2025

TUS-LAS

Very good

8.0 Very good

Greg, Oct 2025

OAK-BUR

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

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.

Everything you need to know for your flight from Boston to Chicago Midway Airport

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Cabin class types available on flights to Chicago Midway Airport

First Class flights from Boston to Chicago Midway Airport

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Economy Class flights from Boston to Chicago Midway Airport

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BOS - MDW

$64 Find Cheap Southwest Flights from Boston to Chicago Midway Airport

Search hundreds of travel sites at once for deals on Southwest flights from Boston to Chicago Midway Airport

Cheap Southwest Flight Deals from Boston to Chicago Midway Airport

Recent round-trip Southwest flight deals from Boston to Chicago Midway Airport

Recent one-way Southwest flight deals from Boston to Chicago Midway Airport

Recent last minute Southwest flight deals from Boston to Chicago Midway Airport

Recent direct Southwest flight deals from Boston to Chicago Midway Airport

Good to know

When to Book Flights with Southwest from Boston to Chicago Midway Airport

FAQs for flying to Chicago Midway Airport with Southwest

What is the cheapest Southwest flight from Boston to Chicago Midway Airport?

Does Southwest fly direct to Chicago Midway Airport from Boston?

What’s the cheapest day of the week to fly from Boston to Chicago Midway Airport with Southwest?

What’s the cheapest month to fly from Boston to Chicago Midway Airport with Southwest?

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Everything you need to know for your flight from Boston to Chicago Midway Airport

Cabin class types available on flights to Chicago Midway Airport

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

Complete your trip to Chicago Midway Airport 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.

Find deals for your return flight

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.