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

1 passenger, economy

Prices updated on 6 November at 11:16

Southwest Airlines: nonstop flights Boston – Chicago Midway International Airport per week: 27. Flight time: 2 hours 45 minutes. Tickets from $99 (departure 14 November).

See also: Airline Southwest Airlines

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

Compare prices, duration and stops

Southwest Airlines
WN 816
18:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
$181
Southwest Airlines
WN 787
16:10
Logan (BOS)
Sat, 7 Nov
8h 25min
1 stop
23:35
Chicago Midway International Airport (MDW)
Sat, 7 Nov
$130
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Mon, 9 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Mon, 9 Nov
$106
Southwest Airlines
WN 813
20:45
Logan (BOS)
Mon, 9 Nov
2h 45min
Direct
22:30
Chicago Midway International Airport (MDW)
Mon, 9 Nov
$135
Southwest Airlines
WN 791
03:30
Logan (BOS)
Tue, 10 Nov
5h 40min
1 stop
08:10
Chicago Midway International Airport (MDW)
Tue, 10 Nov
$113
Southwest Airlines
WN 2758 Best price
15:10
Logan (BOS)
Sat, 14 Nov
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 14 Nov
$99
Southwest Airlines
WN 819
05:10
Logan (BOS)
Sun, 15 Nov
10h
1 stop
14:10
Chicago Midway International Airport (MDW)
Sun, 15 Nov
$158
Southwest Airlines
WN 792
05:35
Logan (BOS)
Sun, 15 Nov
9h 15min
2 stops
13:50
Chicago Midway International Airport (MDW)
Sun, 15 Nov
$137
Southwest Airlines
WN 816
18:30
Logan (BOS)
Sun, 15 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Sun, 15 Nov
$224
Southwest Airlines
WN 816
22:25
Logan (BOS)
Wed, 25 Nov
3h
Direct
00:25
Chicago Midway International Airport (MDW)
Thu, 26 Nov +1
$170
Southwest Airlines
WN 481
15:45
Logan (BOS)
Thu, 26 Nov
9h 35min
1 stop
00:20
Chicago Midway International Airport (MDW)
Fri, 27 Nov +1
$141
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
$101
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Fri, 27 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Fri, 27 Nov
$157
Southwest Airlines
WN 813
12:50
Logan (BOS)
Tue, 1 Dec
2h 50min
Direct
14:40
Chicago Midway International Airport (MDW)
Tue, 1 Dec
$169
Southwest Airlines
WN 813
12:50
Logan (BOS)
Tue, 8 Dec
2h 50min
Direct
14:40
Chicago Midway International Airport (MDW)
Tue, 8 Dec
$106
Southwest Airlines
WN 816
17:55
Logan (BOS)
Thu, 10 Dec
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Thu, 10 Dec
$106
Southwest Airlines
WN 813
12:45
Logan (BOS)
Fri, 11 Dec
2h 45min
Direct
14:30
Chicago Midway International Airport (MDW)
Fri, 11 Dec
$140
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 12 Dec
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 12 Dec
$106
Southwest Airlines
WN 816
18:30
Logan (BOS)
Sun, 13 Dec
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Sun, 13 Dec
$171
Southwest Airlines
WN 4995
15:10
Logan (BOS)
Mon, 14 Dec
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Mon, 14 Dec
$120
Southwest Airlines
WN 816
22:25
Logan (BOS)
Tue, 22 Dec
3h
Direct
00:25
Chicago Midway International Airport (MDW)
Wed, 23 Dec +1
$147
Southwest Airlines
WN 816
06:25
Logan (BOS)
Thu, 24 Dec
2h 55min
Direct
08:20
Chicago Midway International Airport (MDW)
Thu, 24 Dec
$180
Southwest Airlines
WN 800
13:20
Logan (BOS)
Thu, 24 Dec
6h 35min
1 stop
18:55
Chicago Midway International Airport (MDW)
Thu, 24 Dec
$194
Southwest Airlines
WN 1957
17:30
Logan (BOS)
Thu, 24 Dec
5h
1 stop
21:30
Chicago Midway International Airport (MDW)
Thu, 24 Dec
$172
Southwest Airlines
WN 816
01:55
Logan (BOS)
Fri, 25 Dec
2h 45min
Direct
03:40
Chicago Midway International Airport (MDW)
Fri, 25 Dec
$121
Southwest Airlines
WN 816
17:55
Logan (BOS)
Fri, 25 Dec
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Fri, 25 Dec
$140
Southwest Airlines
WN 956
22:20
Logan (BOS)
Sat, 26 Dec
11h 20min
1 stop
08:40
Chicago Midway International Airport (MDW)
Sun, 27 Dec +1
$206
Southwest Airlines
WN 813
19:45
Logan (BOS)
Wed, 30 Dec
2h 45min
Direct
21:30
Chicago Midway International Airport (MDW)
Wed, 30 Dec
$143
Southwest Airlines
WN 816
06:25
Logan (BOS)
Thu, 31 Dec
2h 55min
Direct
08:20
Chicago Midway International Airport (MDW)
Thu, 31 Dec
$145
Southwest Airlines
WN 958
21:10
Logan (BOS)
Thu, 31 Dec
5h 35min
1 stop
01:45
Chicago Midway International Airport (MDW)
Fri, 1 Jan +1
$154
Southwest Airlines
WN 4929
01:10
Logan (BOS)
Sat, 2 Jan
5h 20min
1 stop
05:30
Chicago Midway International Airport (MDW)
Sat, 2 Jan
$171
Southwest Airlines
WN 2939
20:20
Logan (BOS)
Sat, 2 Jan
2h 45min
Direct
22:05
Chicago Midway International Airport (MDW)
Sat, 2 Jan
$283
Southwest Airlines
WN 2185
15:05
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
16:50
Chicago Midway International Airport (MDW)
Mon, 4 Jan
$158
Southwest Airlines
WN 813
12:45
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
14:30
Chicago Midway International Airport (MDW)
Mon, 4 Jan
$103
Southwest Airlines
WN 2758
16:20
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
18:05
Chicago Midway International Airport (MDW)
Mon, 4 Jan
$148
Southwest Airlines
WN 816
18:30
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Mon, 4 Jan
$146
Southwest Airlines
WN 816
01:55
Logan (BOS)
Wed, 6 Jan
2h 45min
Direct
03:40
Chicago Midway International Airport (MDW)
Wed, 6 Jan
$149
Southwest Airlines
WN 4127
07:25
Logan (BOS)
Thu, 21 Jan
2h 50min
Direct
09:15
Chicago Midway International Airport (MDW)
Thu, 21 Jan
$108
Southwest Airlines
WN 698
13:10
Logan (BOS)
Fri, 22 Jan
2h 45min
Direct
14:55
Chicago Midway International Airport (MDW)
Fri, 22 Jan
$108
Southwest Airlines
WN 698
13:10
Logan (BOS)
Mon, 1 Feb
2h 45min
Direct
14:55
Chicago Midway International Airport (MDW)
Mon, 1 Feb
$177
Southwest Airlines
WN 4127
07:15
Logan (BOS)
Mon, 1 Mar
3h
Direct
09:15
Chicago Midway International Airport (MDW)
Mon, 1 Mar
$177
Southwest Airlines
WN 4695
15:30
Logan (BOS)
Fri, 12 Mar
2h 45min
Direct
17:15
Chicago Midway International Airport (MDW)
Fri, 12 Mar
$197
Southwest Airlines
WN 4695
07:30
Logan (BOS)
Tue, 16 Mar
2h 45min
Direct
09:15
Chicago Midway International Airport (MDW)
Tue, 16 Mar
$175
Southwest Airlines
WN 980
13:20
Logan (BOS)
Tue, 16 Mar
2h 45min
Direct
15:05
Chicago Midway International Airport (MDW)
Tue, 16 Mar
$179
Southwest Airlines
WN 4443
01:30
Logan (BOS)
Wed, 17 Mar
2h 50min
Direct
03:20
Chicago Midway International Airport (MDW)
Wed, 17 Mar
$174
Southwest Airlines
WN 4695
07:30
Logan (BOS)
Thu, 1 Apr
2h 45min
Direct
09:15
Chicago Midway International Airport (MDW)
Thu, 1 Apr
$207
Southwest Airlines
WN 329
12:40
Logan (BOS)
Tue, 20 Apr
4h 45min
1 stop
16:25
Chicago Midway International Airport (MDW)
Tue, 20 Apr
$170
Southwest Airlines
WN 744
02:20
Logan (BOS)
Fri, 23 Apr
4h 30min
1 stop
05:50
Chicago Midway International Airport (MDW)
Fri, 23 Apr
$172
Southwest Airlines
WN 633
10:45
Logan (BOS)
Fri, 23 July
2h 40min
Direct
12:25
Chicago Midway International Airport (MDW)
Fri, 23 July
$185

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 $101

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

All →
Flight Departure days Price from
WN2758 MonSat $99
WN0813 Thu $101
WN813 MonTueWedFri $103
WN816 MonTueWedThuFriSun $106
WN2185 MonFri $106
WN4127 MonThu $108
WN698 MonFri $108
WN4995 Mon $120
WN4443 Wed $174
WN4695 TueThuFri $175

Popular destinations from Boston

All →
BOS
Boston — Orlando
United States → United States
ORL
from
$43
BOS
Boston — Washington
United States → United States
WAS
from
$50
BOS
Boston — Lebanon
United States → United States
LEB
from
$67
BOS
Boston — Austin
United States → United States
AUS
from
$68
BOS
Boston — Des Moines
United States → United States
DSM
from
$70
BOS
Boston — Rutland
United States → United States
RUT
from
$74

Popular destinations to Chicago Midway International Airport

All →
DFW
Dallas — Chicago
United States → United States
MDW
from
$55
ATL
Atlanta — Chicago
United States → United States
MDW
from
$67
ORL
Orlando — Chicago
United States → United States
MDW
from
$77
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
$85
DEN
Denver — Chicago
United States → United States
MDW
from
$98
PHL
Philadelphia — Chicago
United States → United States
MDW
from
$99
TPA
Tampa — Chicago
United States → United States
MDW
from
$102
NYC
New York — Chicago
United States → United States
MDW
from
$103
HOU
Houston — Chicago
United States → United States
MDW
from
$110

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

Cheapest flightWN 2758
$99
Fastest flightWN 0813
2h 40min
Average time
2h 47min
Distance
1 382 km

Airports on the Boston — Chicago Midway International Airport route

From → to Flights Direct Price from
LoganBOS Chicago Midway International AirportMDW
2513

Departure airports · Boston

Arrival airports · Chicago Midway International Airport

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
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
$132

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Boston – Chicago Midway International Airport costs $99, 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.