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Flights Chicago – Boston (Logan), Southwest Airlines

1 passenger, economy

Prices updated on 3 November at 11:12

Southwest Airlines: nonstop flights Chicago – Boston per week: 11. Flight time: 2 hours 20 minutes. Tickets from $100 (departure 14 November).

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

Flight schedule Chicago – Boston (Logan), Southwest Airlines

Compare prices, duration and stops

Southwest Airlines
WN 4113
08:30
Chicago Midway International Airport (MDW)
Tue, 3 Nov
2h 30min
Direct
12:00
Logan (BOS)
Tue, 3 Nov
$110
Southwest Airlines
WN 4379
19:15
Chicago Midway International Airport (MDW)
Wed, 4 Nov
2h 15min
Direct
22:30
Logan (BOS)
Wed, 4 Nov
$156
Southwest Airlines
WN 4113
07:50
Chicago Midway International Airport (MDW)
Sun, 8 Nov
2h 20min
Direct
11:10
Logan (BOS)
Sun, 8 Nov
$160
Southwest Airlines
WN 4113 Best price
07:40
Chicago Midway International Airport (MDW)
Sat, 14 Nov
2h 15min
Direct
10:55
Logan (BOS)
Sat, 14 Nov
$100
Southwest Airlines
WN 2902
03:45
Chicago Midway International Airport (MDW)
Tue, 24 Nov
2h 15min
Direct
07:00
Logan (BOS)
Tue, 24 Nov
$120
Southwest Airlines
WN 4113
07:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
2h 20min
Direct
11:05
Logan (BOS)
Thu, 26 Nov
$159
Southwest Airlines
WN 3014
05:35
Chicago Midway International Airport (MDW)
Sun, 29 Nov
2h 15min
Direct
08:50
Logan (BOS)
Sun, 29 Nov
$340
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Fri, 11 Dec
2h 20min
Direct
20:10
Logan (BOS)
Fri, 11 Dec
$130
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Mon, 14 Dec
2h 30min
Direct
21:00
Logan (BOS)
Mon, 14 Dec
$117
Southwest Airlines
WN 2901
01:05
Chicago Midway International Airport (MDW)
Tue, 22 Dec
2h 15min
Direct
04:20
Logan (BOS)
Tue, 22 Dec
$128
Southwest Airlines
WN 2902
18:25
Chicago Midway International Airport (MDW)
Fri, 25 Dec
2h 20min
Direct
21:45
Logan (BOS)
Fri, 25 Dec
$110
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Mon, 4 Jan
2h 20min
Direct
20:10
Logan (BOS)
Mon, 4 Jan
$160
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Tue, 5 Jan
2h 30min
Direct
21:00
Logan (BOS)
Tue, 5 Jan
$150

Southwest Airlines direct flight schedule Chicago — Boston

Direct flights: 2 · First departure: 03:45 · Last departure: 16:50

Departure → arrivalFlightAirport DaysDurationPrice
03:45→07:00 Southwest Airlines WN 2902 Chicago MidwayMDW MonTueWedThuFriSatSun 2h 15min
16:50→20:10 Southwest Airlines WN 4113 Chicago MidwayMDW MonTueWedThuFriSatSun 2h 20min
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 Chicago — Boston

Low price calendar

From
To
Lowest price of the month Thu, 19 Nov · One way from $93

Popular Southwest Airlines flights Chicago – Boston (Logan)

All →
Flight Departure days Price from
WN4113 MonTueThuFriSatSun $100
WN2902 TueFri $110
WN2901 Tue $128
WN4379 Wed $156
WN3014 Sun $340

Popular destinations from Chicago

All →
CHI
Chicago — Denver
United States → United States
DEN
from
$31
CHI
Chicago — Nashville
United States → United States
BNA
from
$33
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
$43
CHI
Chicago — Miami
United States → United States
MIA
from
$50
CHI
Chicago — Phoenix
United States → United States
PHX
from
$58
CHI
Chicago — St Louis
United States → United States
STL
from
$60
CHI
Chicago — Atlanta
United States → United States
ATL
from
$61
CHI
Chicago — Orlando
United States → United States
ORL
from
$65

Popular destinations to Boston

All →
WAS
Washington — Boston
United States → United States
BOS
from
$55
ORL
Orlando — Boston
United States → United States
BOS
from
$60
NYC
New York — Boston
United States → United States
BOS
from
$65
PHL
Philadelphia — Boston
United States → United States
BOS
from
$92
DEN
Denver — Boston
United States → United States
BOS
from
$102
LAS
Las Vegas — Boston
United States → United States
BOS
from
$110
PHX
Phoenix — Boston
United States → United States
BOS
from
$110
BWI
Baltimore — Boston
United States → United States
BOS
from
$117

Flight statistics Chicago – Boston (Logan), Southwest Airlines

Cheapest flightWN 4113
$100
Fastest flightWN 4113
2h 15min
Average time
2h 20min
Distance
1 370 km

Airports on the Chicago — Boston route

From → to Flights Direct Price from
Chicago Midway International AirportMDW LoganBOS
55

Departure airports · Chicago

Arrival airports · Boston

Other airlines Chicago – Boston (Logan)

Frontier Airlines
Frontier Airlines
Mon, Tue, Sat, Sun
Price from
$109
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$150
Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Sat, Sun
Price from
$177
United Airlines
United Airlines
Mon, Wed, Thu, Sat, Sun
Price from
$187

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Chicago – Boston costs $100, flight WN4113, departing at 07:40.
The fastest Southwest Airlines flight Chicago – Boston takes 2h 15min, flight WN4379, departing at 19:15.
The earliest Southwest Airlines flight Chicago – Boston (WN3014) departs at 05:35.