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Flights Chicago – Boston (Logan), Southwest Airlines

1 passenger, economy

Flight schedule Chicago – Boston (Logan), Southwest Airlines

Compare prices, duration and stops

Southwest Airlines
WN 2681
12:40
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
2h 20min
Direct
15:00
Boston, Logan (BOS)
Sat, 19 sep
103 $
Southwest Airlines
WN 3094
10:45
Chicago, Чикаго-Мидвей (MDW)
Mon, 21 sep
2h 15min
Direct
13:00
Boston, Logan (BOS)
Mon, 21 sep
167 $
Southwest Airlines
WN 4215
23:00
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
2h 25min
Direct
01:25
Boston, Logan (BOS)
Wed, 23 sep +1
178 $
Southwest Airlines
WN 1677
11:40
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep
2h 15min
Direct
13:55
Boston, Logan (BOS)
Wed, 23 sep
178 $
Southwest Airlines
WN 2681
11:00
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
2h 15min
Direct
13:15
Boston, Logan (BOS)
Sun, 27 sep
181 $
Southwest Airlines
WN 4860
17:50
Chicago, Чикаго-Мидвей (MDW)
Tue, 29 sep
2h 20min
Direct
20:10
Boston, Logan (BOS)
Tue, 29 sep
144 $
Southwest Airlines
WN 4535
10:00
Chicago, Чикаго-Мидвей (MDW)
Sun, 4 oct
2h 25min
Direct
12:25
Boston, Logan (BOS)
Sun, 4 oct
132 $
Southwest Airlines
WN 2842
14:10
Chicago, Чикаго-Мидвей (MDW)
Wed, 7 oct
2h 20min
Direct
16:30
Boston, Logan (BOS)
Wed, 7 oct
157 $
Southwest Airlines
WN 2851
01:55
Chicago, Чикаго-Мидвей (MDW)
Tue, 13 oct
10h 55min
1 stop
12:50
Boston, Logan (BOS)
Tue, 13 oct
354 $
Southwest Airlines
WN 1687
03:05
Chicago, Чикаго-Мидвей (MDW)
Tue, 13 oct
11h 10min
1 stop
14:15
Boston, Logan (BOS)
Tue, 13 oct
141 $
Southwest Airlines
WN 4113
13:50
Chicago, Чикаго-Мидвей (MDW)
Sun, 1 nov
2h 20min
Direct
16:10
Boston, Logan (BOS)
Sun, 1 nov
120 $
Southwest Airlines
WN 2902
00:45
Chicago, Чикаго-Мидвей (MDW)
Tue, 24 nov
2h 15min
Direct
03:00
Boston, Logan (BOS)
Tue, 24 nov
116 $
Southwest Airlines
WN 4113 Best price
13:45
Chicago, Чикаго-Мидвей (MDW)
Thu, 26 nov
2h 20min
Direct
16:05
Boston, Logan (BOS)
Thu, 26 nov
97 $
Southwest Airlines
WN 4113
13:50
Chicago, Чикаго-Мидвей (MDW)
Fri, 11 dec
2h 20min
Direct
16:10
Boston, Logan (BOS)
Fri, 11 dec
125 $
Southwest Airlines
WN 4113
14:30
Chicago, Чикаго-Мидвей (MDW)
Mon, 14 dec
2h 30min
Direct
17:00
Boston, Logan (BOS)
Mon, 14 dec
112 $
Southwest Airlines
WN 2901
22:05
Chicago, Чикаго-Мидвей (MDW)
Mon, 21 dec
2h 15min
Direct
00:20
Boston, Logan (BOS)
Tue, 22 dec +1
124 $
Southwest Airlines
WN 4113
14:30
Chicago, Чикаго-Мидвей (MDW)
Tue, 5 jan
2h 30min
Direct
17:00
Boston, Logan (BOS)
Tue, 5 jan
145 $

Low price calendar

September 2026
Price chart (September 2026)
min: 99 $ · max: 181 $
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120 $
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107 $
19
Good deal
102 $
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167 $
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145 $
22
Good deal
99 $
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178 $
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181 $
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138 $
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144 $
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Popular Southwest Airlines flights Chicago – Boston (Logan)

All →
Flight Departure days Price from
WN4113 MonTueThuFriSun $97
WN2681 SatSun $103
WN2902 Tue $116
WN3094 MonThu $120
WN2901 Mon $124
WN4535 Sun $132
WN1687 Tue $141
WN4860 Tue $144
WN2842 Wed $157
WN4215 Tue $178

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
$21
CHI
Chicago — Orlando
United States → United States
MCO
from
$21
CHI
Chicago — Atlanta
United States → United States
ATL
from
$22
CHI
Chicago — Houston
United States → United States
IAH
from
$22
CHI
Chicago — Houston
United States → United States
HOU
from
$22
CHI
Chicago — New York
United States → United States
NYC
from
$23
CHI
Chicago — Denver
United States → United States
DEN
from
$24
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
$24
CHI
Chicago — Miami
United States → United States
MIA
from
$25

Popular destinations to Boston

All →
ORL
Orlando — Boston
United States → United States
BOS
from
$27
FLL
Fort Lauderdale — Boston
United States → United States
BOS
from
$44
WAS
Washington — Boston
United States → United States
BOS
from
$45
NYC
New York — Boston
United States → United States
BOS
from
$60
MIA
Miami — Boston
United States → United States
BOS
from
$68
ATL
Atlanta — Boston
United States → United States
BOS
from
$74
BUF
Buffalo — Boston
United States → United States
BOS
from
$77
LAX
Los Angeles — Boston
United States → United States
BOS
from
$79

Flight statistics Chicago – Boston (Logan), Southwest Airlines

We gathered interesting facts about the flight for you

Cheapest flight

WN 4113

$97

Fastest flight

WN 2902

2h 15min

Average time

3h 18min

Distance

1 370 km

Passenger reviews

No reviews for this route yet

Other airlines Chicago – Boston (Logan)

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$97
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$102
Frontier Airlines
Frontier Airlines
Thu, Fri, Sat
Price from
$139
American Airlines
American Airlines
Wed, Thu, Sat, Sun
Price from
$145

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Chicago – Boston costs $97, flight WN4113, departing at 13:45.
The fastest Southwest Airlines flight Chicago – Boston takes 2h 15min, flight WN3094, departing at 10:45.
The earliest Southwest Airlines flight Chicago – Boston (WN2681) departs at 12:40.