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Flights Boston (Logan) – Chicago, Southwest Airlines

1 passenger, economy

Prices updated on 3 November at 11:12

Southwest Airlines: nonstop flights Boston – Chicago per week: 15. Flight time: 2 hours 45 minutes. Tickets from C$140 (departure 14 November).

See also: Chicago — Boston (Logan), Southwest AirlinesAirline Southwest Airlines

Flight schedule Boston (Logan) – Chicago, Southwest Airlines

Compare prices, duration and stops

Southwest Airlines
WN 816
17:55
Logan (BOS)
Tue, 3 Nov
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Tue, 3 Nov
C$153
Southwest Airlines
WN 816
18:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
C$255
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
C$140
Southwest Airlines
WN 816
22:25
Logan (BOS)
Wed, 25 Nov
3h
Direct
00:25
Chicago Midway International Airport (MDW)
Thu, 26 Nov +1
C$239
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
C$142
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Fri, 27 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Fri, 27 Nov
C$221
Southwest Airlines
WN 813
12:50
Logan (BOS)
Tue, 8 Dec
2h 50min
Direct
14:40
Chicago Midway International Airport (MDW)
Tue, 8 Dec
C$150
Southwest Airlines
WN 816
17:55
Logan (BOS)
Thu, 10 Dec
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Thu, 10 Dec
C$150
Southwest Airlines
WN 813
12:45
Logan (BOS)
Fri, 11 Dec
2h 45min
Direct
14:30
Chicago Midway International Airport (MDW)
Fri, 11 Dec
C$198
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 12 Dec
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 12 Dec
C$150
Southwest Airlines
WN 816
18:30
Logan (BOS)
Sun, 13 Dec
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Sun, 13 Dec
C$242
Southwest Airlines
WN 816
22:25
Logan (BOS)
Tue, 22 Dec
3h
Direct
00:25
Chicago Midway International Airport (MDW)
Wed, 23 Dec +1
C$207
Southwest Airlines
WN 2185
15:05
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
16:50
Chicago Midway International Airport (MDW)
Mon, 4 Jan
C$223
Southwest Airlines
WN 813
12:45
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
14:30
Chicago Midway International Airport (MDW)
Mon, 4 Jan
C$145
Southwest Airlines
WN 2758
16:20
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
18:05
Chicago Midway International Airport (MDW)
Mon, 4 Jan
C$208
Southwest Airlines
WN 816
18:30
Logan (BOS)
Mon, 4 Jan
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Mon, 4 Jan
C$206
Southwest Airlines
WN 816
01:55
Logan (BOS)
Wed, 6 Jan
2h 45min
Direct
03:40
Chicago Midway International Airport (MDW)
Wed, 6 Jan
C$210
Southwest Airlines
WN 698
13:10
Logan (BOS)
Fri, 22 Jan
2h 45min
Direct
14:55
Chicago Midway International Airport (MDW)
Fri, 22 Jan
C$152

Southwest Airlines direct flight schedule Boston — Chicago

Direct flights: 4 · First departure: 07:05 · Last departure: 18:30

Departure → arrivalFlightAirport DaysDurationPrice
07:05→08:50 Southwest Airlines WN 2185 LoganBOS MonTueWedThuFriSatSun 2h 45min
12:45→14:30 Southwest Airlines WN 813 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.

Direct flights by other airlines: 7 Full schedule Boston — Chicago

Low price calendar

From
To
Lowest price of the month Thu, 5 Nov · One way from C$137

Popular Southwest Airlines flights Boston (Logan) – Chicago

All →
Flight Departure days Price from
WN2758 MonSat C$140
WN0813 Thu C$142
WN813 MonTueFri C$145
WN816 MonTueWedThuFriSun C$150
WN698 Fri C$152
WN2185 MonFri C$221

Popular destinations from Boston

All →
BOS
Boston — Washington
United States → United States
WAS
from
C$71
BOS
Boston — Orlando
United States → United States
ORL
from
C$84
BOS
Boston — Austin
United States → United States
AUS
from
C$96
BOS
Boston — Lebanon
United States → United States
LEB
from
C$96
BOS
Boston — Rutland
United States → United States
RUT
from
C$104
BOS
Boston — Fort Lauderdale
United States → United States
FLL
from
C$110

Popular destinations to Chicago

All →
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
C$48
ORL
Orlando — Chicago
United States → United States
CHI
from
C$64
BNA
Nashville — Chicago
United States → United States
CHI
from
C$67
DEN
Denver — Chicago
United States → United States
CHI
from
C$75
TPA
Tampa — Chicago
United States → United States
CHI
from
C$75
DFW
Dallas — Chicago
United States → United States
CHI
from
C$76
ATL
Atlanta — Chicago
United States → United States
CHI
from
C$94
LAX
Los Angeles — Chicago
United States → United States
CHI
from
C$106
PHL
Philadelphia — Chicago
United States → United States
CHI
from
C$109

Flight statistics Boston (Logan) – Chicago, Southwest Airlines

Cheapest flightWN 2758
C$140
Fastest flightWN 0813
2h 40min
Average time
2h 46min
Distance
1 370 km

Airports on the Boston — Chicago route

From → to Flights Direct Price from
LoganBOS Chicago Midway International AirportMDW
66

Departure airports · Boston

Arrival airports · Chicago

Трансфер из аэропорта O'Hare International Airport

Индивидуальная машина до курорта или отеля

Расстояние и время в пути — ориентировочные

Other airlines Boston (Logan) – Chicago

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri
Price from
C$148
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
C$162
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
C$163

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Boston – Chicago costs C$140, flight WN2758, departing at 15:10.
The fastest Southwest Airlines flight Boston – Chicago takes 2h 40min, flight WN0813, departing at 13:05.
The earliest Southwest Airlines flight Boston – Chicago (WN2185) departs at 07:05.