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Flights Chicago – New York, Southwest Airlines

1 passenger, economy

Flight schedule Chicago – New York, Southwest Airlines

Compare prices, duration and stops

Southwest Airlines
WN 4797
17:10
Chicago, Чикаго-Мидвей (MDW)
Sat, 12 sep
2h 10min
Direct
19:20
New York, Ла Гуардиа (LGA)
Sat, 12 sep
77 $
Southwest Airlines
WN 3948
10:00
Chicago, Чикаго-Мидвей (MDW)
Mon, 14 sep
2h
Direct
12:00
New York, Ла Гуардиа (LGA)
Mon, 14 sep
106 $
Southwest Airlines
WN 269
14:35
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
2h 5min
Direct
16:40
New York, Ла Гуардиа (LGA)
Sat, 19 sep
147 $
Southwest Airlines
WN 4797
17:10
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
2h 10min
Direct
19:20
New York, Ла Гуардиа (LGA)
Sat, 19 sep
78 $
Southwest Airlines
WN 3183
10:25
Chicago, Чикаго-Мидвей (MDW)
Sun, 20 sep
2h
Direct
12:25
New York, Ла Гуардиа (LGA)
Sun, 20 sep
119 $
Southwest Airlines
WN 3948
10:00
Chicago, Чикаго-Мидвей (MDW)
Mon, 21 sep
2h
Direct
12:00
New York, Ла Гуардиа (LGA)
Mon, 21 sep
130 $
Southwest Airlines
WN 4236 Best price
22:45
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
2h 10min
Direct
00:55
New York, Ла Гуардиа (LGA)
Wed, 23 sep +1
77 $
Southwest Airlines
WN 487
00:50
Chicago, Чикаго-Мидвей (MDW)
Sat, 26 sep
2h 5min
Direct
02:55
New York, Ла Гуардиа (LGA)
Sat, 26 sep
110 $
Southwest Airlines
WN 4198
11:00
Chicago, Чикаго-Мидвей (MDW)
Sat, 26 sep
2h
Direct
13:00
New York, Ла Гуардиа (LGA)
Sat, 26 sep
127 $
Southwest Airlines
WN 3183
10:25
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
2h
Direct
12:25
New York, Ла Гуардиа (LGA)
Sun, 27 sep
143 $
Southwest Airlines
WN 2013
22:10
Chicago, Чикаго-Мидвей (MDW)
Mon, 28 sep
2h 5min
Direct
00:15
New York, Ла Гуардиа (LGA)
Tue, 29 sep +1
84 $
Southwest Airlines
WN 2905
10:10
Chicago, Чикаго-Мидвей (MDW)
Thu, 1 oct
2h 5min
Direct
12:15
New York, Ла Гуардиа (LGA)
Thu, 1 oct
148 $
Southwest Airlines
WN 2905
10:05
Chicago, Чикаго-Мидвей (MDW)
Sun, 4 oct
2h 5min
Direct
12:10
New York, Ла Гуардиа (LGA)
Sun, 4 oct
135 $
Southwest Airlines
WN 2905
10:10
Chicago, Чикаго-Мидвей (MDW)
Mon, 5 oct
2h 5min
Direct
12:15
New York, Ла Гуардиа (LGA)
Mon, 5 oct
81 $
Southwest Airlines
WN 309
00:35
Chicago, Чикаго-Мидвей (MDW)
Tue, 6 oct
2h 10min
Direct
02:45
New York, Ла Гуардиа (LGA)
Tue, 6 oct
134 $
Southwest Airlines
WN 2905
10:00
Chicago, Чикаго-Мидвей (MDW)
Tue, 6 oct
2h 5min
Direct
12:05
New York, Ла Гуардиа (LGA)
Tue, 6 oct
83 $
Southwest Airlines
WN 2745
22:10
Chicago, Чикаго-Мидвей (MDW)
Wed, 7 oct
2h 5min
Direct
00:15
New York, Ла Гуардиа (LGA)
Thu, 8 oct +1
100 $
Southwest Airlines
WN 2905
10:10
Chicago, Чикаго-Мидвей (MDW)
Fri, 9 oct
2h 5min
Direct
12:15
New York, Ла Гуардиа (LGA)
Fri, 9 oct
110 $
Southwest Airlines
WN 2905
10:05
Chicago, Чикаго-Мидвей (MDW)
Sun, 11 oct
2h 5min
Direct
12:10
New York, Ла Гуардиа (LGA)
Sun, 11 oct
141 $
Southwest Airlines
WN 1162
00:25
Chicago, Чикаго-Мидвей (MDW)
Wed, 14 oct
2h 5min
Direct
02:30
New York, Ла Гуардиа (LGA)
Wed, 14 oct
129 $
Southwest Airlines
WN 2905
10:05
Chicago, Чикаго-Мидвей (MDW)
Sun, 25 oct
2h 5min
Direct
12:10
New York, Ла Гуардиа (LGA)
Sun, 25 oct
141 $
Southwest Airlines
WN 258
18:30
Chicago, Чикаго-Мидвей (MDW)
Tue, 3 nov
2h 5min
Direct
20:35
New York, Ла Гуардиа (LGA)
Tue, 3 nov
108 $
Southwest Airlines
WN 2958
01:15
Chicago, Чикаго-Мидвей (MDW)
Tue, 10 nov
2h 5min
Direct
03:20
New York, Ла Гуардиа (LGA)
Tue, 10 nov
130 $
Southwest Airlines
WN 921
23:15
Chicago, Чикаго-Мидвей (MDW)
Thu, 12 nov
2h 5min
Direct
01:20
New York, Ла Гуардиа (LGA)
Fri, 13 nov +1
85 $
Southwest Airlines
WN 921
23:15
Chicago, Чикаго-Мидвей (MDW)
Fri, 13 nov
2h 5min
Direct
01:20
New York, Ла Гуардиа (LGA)
Sat, 14 nov +1
127 $
Southwest Airlines
WN 814
11:00
Chicago, Чикаго-Мидвей (MDW)
Fri, 20 nov
2h 5min
Direct
13:05
New York, Ла Гуардиа (LGA)
Fri, 20 nov
114 $
Southwest Airlines
WN 814
11:00
Chicago, Чикаго-Мидвей (MDW)
Mon, 23 nov
2h 5min
Direct
13:05
New York, Ла Гуардиа (LGA)
Mon, 23 nov
130 $
Southwest Airlines
WN 4731
01:40
Chicago, Чикаго-Мидвей (MDW)
Tue, 19 jan
2h
Direct
03:40
New York, Ла Гуардиа (LGA)
Tue, 19 jan
137 $

Low price calendar

September 2026
Price chart (September 2026)
min: 84 $ · max: 139 $
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Mon
Tue
Wed
Thu
Fri
Sat
Sun
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109 $
13
Good deal
84 $
14
Good deal
106 $
15
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131 $
16
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122 $
17
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132 $
18
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130 $
19
Good deal
108 $
20
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119 $
21
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132 $
22
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128 $
23
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113 $
24
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139 $
25
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118 $
26
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137 $
27
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113 $
28
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136 $
29
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128 $
30
Good deal
103 $

Popular Southwest Airlines flights Chicago – New York

All →
Flight Departure days Price from
WN4236 Tue $77
WN4797 Sat $77
WN2905 MonTueThuFriSun $81
WN2013 Mon $84
WN921 ThuFri $85
WN2745 Wed $100
WN3948 Mon $106
WN258 Tue $108
WN487 Sat $110
WN814 MonFri $114

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 — 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 New York

All →
ORL
Orlando — New York
United States → United States
NYC
from
$18
ATL
Atlanta — New York
United States → United States
NYC
from
$22
FLL
Fort Lauderdale — New York
United States → United States
NYC
from
$29
MIA
Miami — New York
United States → United States
NYC
from
$35
DFW
Dallas — New York
United States → United States
NYC
from
$55
TPA
Tampa — New York
United States → United States
NYC
from
$56
RDU
Raleigh — New York
United States → United States
NYC
from
$62
LAX
Los Angeles — New York
United States → United States
NYC
from
$69

Flight statistics Chicago – New York, Southwest Airlines

We gathered interesting facts about the flight for you

Cheapest flight

WN 4236

$77

Fastest flight

WN 3948

2h

Average time

2h 4min

Distance

1 144 km

Passenger reviews

No reviews for this route yet

Other airlines Chicago – New York

Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$85
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$108
Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sat
Price from
$111
United Airlines
United Airlines
Tue, Wed, Thu, Fri, Sat, Sun
Price from
$111

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15

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Chicago – New York costs $77, flight WN4236, departing at 22:45.
The fastest Southwest Airlines flight Chicago – New York takes 2h, flight WN3948, departing at 10:00.
The earliest Southwest Airlines flight Chicago – New York (WN4797) departs at 17:10.