Flights Boston (Logan) – Chicago Midway International Airport, Southwest Airlines

From

To

Depart

Return

Passengers

1 passenger, economy

Prices updated on 5 November at 11:13

Southwest Airlines: nonstop flights Boston – Chicago Midway International Airport per week: 27. Flight time: 2 hours 45 minutes. Tickets from C$138 (departure 14 November).

See also: Airline Southwest Airlines

Flight schedule Boston (Logan) – Chicago Midway International Airport, Southwest Airlines

Compare prices, duration and stops

Filters

Stops

Direct only 1 stop 2+ stops

Price

C$138 C$395 C$395

WN 816

02:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

C$166

WN 816

18:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

C$252

WN 787

16:10

Logan (BOS)

Sat, 7 Nov

8h 25min

1 stop

23:35

Chicago Midway International Airport (MDW)

Sat, 7 Nov

C$181

WN 2185

07:05

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Mon, 9 Nov

C$149

WN 813

20:45

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

22:30

Chicago Midway International Airport (MDW)

Mon, 9 Nov

C$189

WN 791

03:30

Logan (BOS)

Tue, 10 Nov

5h 40min

1 stop

08:10

Chicago Midway International Airport (MDW)

Tue, 10 Nov

C$157

WN 2758 Best price

15:10

Logan (BOS)

Sat, 14 Nov

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 14 Nov

C$138

WN 819

05:10

Logan (BOS)

Sun, 15 Nov

10h

1 stop

14:10

Chicago Midway International Airport (MDW)

Sun, 15 Nov

C$220

WN 792

05:35

Logan (BOS)

Sun, 15 Nov

9h 15min

2 stops

13:50

Chicago Midway International Airport (MDW)

Sun, 15 Nov

C$191

WN 816

18:30

Logan (BOS)

Sun, 15 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Sun, 15 Nov

C$313

WN 816

22:25

Logan (BOS)

Wed, 25 Nov

3h

Direct

00:25

Chicago Midway International Airport (MDW)

Thu, 26 Nov +1

C$237

WN 481

15:45

Logan (BOS)

Thu, 26 Nov

9h 35min

1 stop

00:20

Chicago Midway International Airport (MDW)

Fri, 27 Nov +1

C$196

WN 0813

13:05

Logan (BOS)

Thu, 26 Nov

2h 40min

Direct

14:45

Chicago Midway International Airport (MDW)

Thu, 26 Nov

C$140

WN 2185

07:05

Logan (BOS)

Fri, 27 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Fri, 27 Nov

C$219

WN 813

12:50

Logan (BOS)

Tue, 1 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 1 Dec

C$236

WN 813

12:50

Logan (BOS)

Tue, 8 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 8 Dec

C$148

WN 816

17:55

Logan (BOS)

Thu, 10 Dec

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Thu, 10 Dec

C$148

WN 813

12:45

Logan (BOS)

Fri, 11 Dec

2h 45min

Direct

14:30

Chicago Midway International Airport (MDW)

Fri, 11 Dec

C$196

WN 2758

15:10

Logan (BOS)

Sat, 12 Dec

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 12 Dec

C$148

WN 816

18:30

Logan (BOS)

Sun, 13 Dec

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Sun, 13 Dec

C$239

WN 4995

15:10

Logan (BOS)

Mon, 14 Dec

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Mon, 14 Dec

C$167

WN 816

22:25

Logan (BOS)

Tue, 22 Dec

3h

Direct

00:25

Chicago Midway International Airport (MDW)

Wed, 23 Dec +1

C$205

WN 816

06:25

Logan (BOS)

Thu, 24 Dec

2h 55min

Direct

08:20

Chicago Midway International Airport (MDW)

Thu, 24 Dec

C$251

WN 800

13:20

Logan (BOS)

Thu, 24 Dec

6h 35min

1 stop

18:55

Chicago Midway International Airport (MDW)

Thu, 24 Dec

C$271

WN 1957

17:30

Logan (BOS)

Thu, 24 Dec

5h

1 stop

21:30

Chicago Midway International Airport (MDW)

Thu, 24 Dec

C$254

WN 816

01:55

Logan (BOS)

Fri, 25 Dec

2h 45min

Direct

03:40

Chicago Midway International Airport (MDW)

Fri, 25 Dec

C$169

WN 816

17:55

Logan (BOS)

Fri, 25 Dec

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Fri, 25 Dec

C$195

WN 956

22:20

Logan (BOS)

Sat, 26 Dec

11h 20min

1 stop

08:40

Chicago Midway International Airport (MDW)

Sun, 27 Dec +1

C$288

WN 813

19:45

Logan (BOS)

Wed, 30 Dec

2h 45min

Direct

21:30

Chicago Midway International Airport (MDW)

Wed, 30 Dec

C$200

WN 816

06:25

Logan (BOS)

Thu, 31 Dec

2h 55min

Direct

08:20

Chicago Midway International Airport (MDW)

Thu, 31 Dec

C$202

WN 958

21:10

Logan (BOS)

Thu, 31 Dec

5h 35min

1 stop

01:45

Chicago Midway International Airport (MDW)

Fri, 1 Jan +1

C$215

WN 4929

01:10

Logan (BOS)

Sat, 2 Jan

5h 20min

1 stop

05:30

Chicago Midway International Airport (MDW)

Sat, 2 Jan

C$239

WN 2939

20:20

Logan (BOS)

Sat, 2 Jan

2h 45min

Direct

22:05

Chicago Midway International Airport (MDW)

Sat, 2 Jan

C$395

WN 2185

15:05

Logan (BOS)

Mon, 4 Jan

2h 45min

Direct

16:50

Chicago Midway International Airport (MDW)

Mon, 4 Jan

C$221

WN 813

12:45

Logan (BOS)

Mon, 4 Jan

2h 45min

Direct

14:30

Chicago Midway International Airport (MDW)

Mon, 4 Jan

C$143

WN 2758

16:20

Logan (BOS)

Mon, 4 Jan

2h 45min

Direct

18:05

Chicago Midway International Airport (MDW)

Mon, 4 Jan

C$206

WN 816

18:30

Logan (BOS)

Mon, 4 Jan

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Mon, 4 Jan

C$204

WN 816

01:55

Logan (BOS)

Wed, 6 Jan

2h 45min

Direct

03:40

Chicago Midway International Airport (MDW)

Wed, 6 Jan

C$207

WN 4127

07:25

Logan (BOS)

Thu, 21 Jan

2h 50min

Direct

09:15

Chicago Midway International Airport (MDW)

Thu, 21 Jan

C$151

WN 698

13:10

Logan (BOS)

Fri, 22 Jan

2h 45min

Direct

14:55

Chicago Midway International Airport (MDW)

Fri, 22 Jan

C$151

WN 698

13:10

Logan (BOS)

Mon, 1 Feb

2h 45min

Direct

14:55

Chicago Midway International Airport (MDW)

Mon, 1 Feb

C$247

WN 4127

07:15

Logan (BOS)

Mon, 1 Mar

3h

Direct

09:15

Chicago Midway International Airport (MDW)

Mon, 1 Mar

C$247

WN 4695

15:30

Logan (BOS)

Fri, 12 Mar

2h 45min

Direct

17:15

Chicago Midway International Airport (MDW)

Fri, 12 Mar

C$276

WN 4695

07:30

Logan (BOS)

Tue, 16 Mar

2h 45min

Direct

09:15

Chicago Midway International Airport (MDW)

Tue, 16 Mar

C$244

WN 980

13:20

Logan (BOS)

Tue, 16 Mar

2h 45min

Direct

15:05

Chicago Midway International Airport (MDW)

Tue, 16 Mar

C$250

WN 4443

01:30

Logan (BOS)

Wed, 17 Mar

2h 50min

Direct

03:20

Chicago Midway International Airport (MDW)

Wed, 17 Mar

C$243

WN 4695

07:30

Logan (BOS)

Thu, 1 Apr

2h 45min

Direct

09:15

Chicago Midway International Airport (MDW)

Thu, 1 Apr

C$289

WN 329

12:40

Logan (BOS)

Tue, 20 Apr

4h 45min

1 stop

16:25

Chicago Midway International Airport (MDW)

Tue, 20 Apr

C$237

WN 744

02:20

Logan (BOS)

Fri, 23 Apr

4h 30min

1 stop

05:50

Chicago Midway International Airport (MDW)

Fri, 23 Apr

C$240

WN 633

10:45

Logan (BOS)

Fri, 23 July

2h 40min

Direct

12:25

Chicago Midway International Airport (MDW)

Fri, 23 July

C$258

Southwest Airlines direct flight schedule Boston — Chicago Midway International Airport

Direct flights: 7 · First departure: 07:05 · Last departure: 18:30

Departure → arrivalFlightAirport DaysDurationPrice

07:05→08:50 Southwest Airlines WN 2185 LoganBOS MonTueWedThuFriSatSun 2h 45min

07:15→09:05 Southwest Airlines WN 4127 LoganBOS MonTueWedThuFriSatSun 2h 50min

07:30→09:15 Southwest Airlines WN 4695 LoganBOS MonTueWedThuFriSatSun 2h 45min

12:45→14:30 Southwest Airlines WN 813 LoganBOS MonTueWedThuFriSatSun 2h 45min

13:10→14:55 Southwest Airlines WN 698 LoganBOS MonTueWedThuFriSatSun 2h 45min

15:10→16:55 Southwest Airlines WN 2758 LoganBOS MonTueWedThuFriSatSun 2h 45min

18:30→20:15 Southwest Airlines WN 816 LoganBOS MonTueWedThuFriSatSun 2h 45min

Local time: departure at the departure airport, arrival at the arrival airport. Days and prices are based on tickets found for the coming months.

Low price calendar

From

To

Lowest price of the month Thu, 26 Nov · One way from C$140

Popular Southwest Airlines flights Boston (Logan) – Chicago Midway International Airport

All →

Flight	Departure days	Price from
WN2758	MonSat	C$138
WN0813	Thu	C$140
WN813	MonTueWedFri	C$143
WN816	MonTueWedThuFriSun	C$148
WN2185	MonFri	C$149
WN4127	MonThu	C$151
WN698	MonFri	C$151
WN4995	Mon	C$167
WN4443	Wed	C$243
WN4695	TueThuFri	C$244

Popular destinations from Boston

All →

BOS

Boston — Orlando

United States → United States

ORL

from

C$60

BOS

Boston — Washington

United States → United States

WAS

from

C$70

BOS

Boston — Lebanon

United States → United States

LEB

from

C$94

BOS

Boston — Austin

United States → United States

AUS

from

C$95

BOS

Boston — Des Moines

United States → United States

DSM

from

C$98

BOS

Boston — Rutland

United States → United States

RUT

from

C$103

Popular destinations to Chicago Midway International Airport

All →

DFW

Dallas — Chicago

United States → United States

MDW

from

C$75

ATL

Atlanta — Chicago

United States → United States

MDW

from

C$93

ORL

Orlando — Chicago

United States → United States

MDW

from

C$117

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

C$119

PHL

Philadelphia — Chicago

United States → United States

MDW

from

C$135

DEN

Denver — Chicago

United States → United States

MDW

from

C$136

TPA

Tampa — Chicago

United States → United States

MDW

from

C$142

NYC

New York — Chicago

United States → United States

MDW

from

C$144

LAX

Los Angeles — Chicago

United States → United States

MDW

from

C$159

Flight statistics Boston (Logan) – Chicago Midway International Airport, Southwest Airlines

Cheapest flightWN 2758: C$138
Fastest flightWN 0813: 2h 40min
Average time: 2h 46min
Distance: 1 382 km

Airports on the Boston — Chicago Midway International Airport route

From → to	Flights	Direct	Price from
LoganBOS Chicago Midway International AirportMDW	25	13

Departure airports · Boston

LoganBOS

Arrival airports · Chicago Midway International Airport

Chicago Midway International AirportMDW ≈ 14 km from the centre

Трансфер из аэропорта Chicago Midway International Airport

Индивидуальная машина до курорта или отеля

Расстояние и время в пути — ориентировочные

Other airlines Boston (Logan) – Chicago Midway International Airport

Frontier Airlines

Mon, Tue, Wed, Thu, Fri, Sat

Price from

C$163

Internet abroad

eSIM · United States

change

3 GB

data

30

days

C$13

change

2 GB

data

15

days

C$17

change

5 GB

data

30

days

C$20

change

3 GB

data

30

days

C$22

change

5 GB

data

30

days

C$31

Frequently Asked Questions

The cheapest Southwest Airlines ticket Boston – Chicago Midway International Airport costs C$138, flight WN2758, departing at 15:10.

The fastest Southwest Airlines flight Boston – Chicago Midway International Airport takes 2h 40min, flight WN0813, departing at 13:05.

The earliest Southwest Airlines flight Boston – Chicago Midway International Airport (WN816) departs at 06:25.