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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, Chicago Midway International Airport (MDW)
Sat, 12 sep
2h 10min
Direct
19:20
New York, LaGuardia Airport (LGA)
Sat, 12 sep
133 NZ$
Southwest Airlines
WN 3948
10:00
Chicago, Chicago Midway International Airport (MDW)
Mon, 14 sep
2h
Direct
12:00
New York, LaGuardia Airport (LGA)
Mon, 14 sep
182 NZ$
Southwest Airlines
WN 269
14:35
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
2h 5min
Direct
16:40
New York, LaGuardia Airport (LGA)
Sat, 19 sep
253 NZ$
Southwest Airlines
WN 4797
17:10
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
2h 10min
Direct
19:20
New York, LaGuardia Airport (LGA)
Sat, 19 sep
135 NZ$
Southwest Airlines
WN 3183
10:25
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
2h
Direct
12:25
New York, LaGuardia Airport (LGA)
Sun, 20 sep
204 NZ$
Southwest Airlines
WN 3948
10:00
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
2h
Direct
12:00
New York, LaGuardia Airport (LGA)
Mon, 21 sep
224 NZ$
Southwest Airlines
WN 4236 Best price
22:45
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
2h 10min
Direct
00:55
New York, LaGuardia Airport (LGA)
Wed, 23 sep +1
133 NZ$
Southwest Airlines
WN 487
00:50
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
2h 5min
Direct
02:55
New York, LaGuardia Airport (LGA)
Sat, 26 sep
188 NZ$
Southwest Airlines
WN 4198
11:00
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
2h
Direct
13:00
New York, LaGuardia Airport (LGA)
Sat, 26 sep
218 NZ$
Southwest Airlines
WN 3183
10:25
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
2h
Direct
12:25
New York, LaGuardia Airport (LGA)
Sun, 27 sep
246 NZ$
Southwest Airlines
WN 2013
22:10
Chicago, Chicago Midway International Airport (MDW)
Mon, 28 sep
2h 5min
Direct
00:15
New York, LaGuardia Airport (LGA)
Tue, 29 sep +1
144 NZ$
Southwest Airlines
WN 2905
10:10
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
2h 5min
Direct
12:15
New York, LaGuardia Airport (LGA)
Thu, 1 oct
254 NZ$
Southwest Airlines
WN 2905
10:05
Chicago, Chicago Midway International Airport (MDW)
Sun, 4 oct
2h 5min
Direct
12:10
New York, LaGuardia Airport (LGA)
Sun, 4 oct
233 NZ$
Southwest Airlines
WN 2905
10:10
Chicago, Chicago Midway International Airport (MDW)
Mon, 5 oct
2h 5min
Direct
12:15
New York, LaGuardia Airport (LGA)
Mon, 5 oct
140 NZ$
Southwest Airlines
WN 309
00:35
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
2h 10min
Direct
02:45
New York, LaGuardia Airport (LGA)
Tue, 6 oct
231 NZ$
Southwest Airlines
WN 2905
10:00
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
2h 5min
Direct
12:05
New York, LaGuardia Airport (LGA)
Tue, 6 oct
143 NZ$
Southwest Airlines
WN 2745
22:10
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
2h 5min
Direct
00:15
New York, LaGuardia Airport (LGA)
Thu, 8 oct +1
173 NZ$
Southwest Airlines
WN 2905
10:10
Chicago, Chicago Midway International Airport (MDW)
Fri, 9 oct
2h 5min
Direct
12:15
New York, LaGuardia Airport (LGA)
Fri, 9 oct
189 NZ$
Southwest Airlines
WN 2905
10:05
Chicago, Chicago Midway International Airport (MDW)
Sun, 11 oct
2h 5min
Direct
12:10
New York, LaGuardia Airport (LGA)
Sun, 11 oct
243 NZ$
Southwest Airlines
WN 1162
00:25
Chicago, Chicago Midway International Airport (MDW)
Wed, 14 oct
2h 5min
Direct
02:30
New York, LaGuardia Airport (LGA)
Wed, 14 oct
221 NZ$
Southwest Airlines
WN 2905
10:05
Chicago, Chicago Midway International Airport (MDW)
Sun, 25 oct
2h 5min
Direct
12:10
New York, LaGuardia Airport (LGA)
Sun, 25 oct
243 NZ$
Southwest Airlines
WN 258
18:30
Chicago, Chicago Midway International Airport (MDW)
Tue, 3 nov
2h 5min
Direct
20:35
New York, LaGuardia Airport (LGA)
Tue, 3 nov
186 NZ$
Southwest Airlines
WN 2958
01:15
Chicago, Chicago Midway International Airport (MDW)
Tue, 10 nov
2h 5min
Direct
03:20
New York, LaGuardia Airport (LGA)
Tue, 10 nov
223 NZ$
Southwest Airlines
WN 921
23:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 12 nov
2h 5min
Direct
01:20
New York, LaGuardia Airport (LGA)
Fri, 13 nov +1
146 NZ$
Southwest Airlines
WN 921
23:15
Chicago, Chicago Midway International Airport (MDW)
Fri, 13 nov
2h 5min
Direct
01:20
New York, LaGuardia Airport (LGA)
Sat, 14 nov +1
218 NZ$
Southwest Airlines
WN 814
11:00
Chicago, Chicago Midway International Airport (MDW)
Fri, 20 nov
2h 5min
Direct
13:05
New York, LaGuardia Airport (LGA)
Fri, 20 nov
197 NZ$
Southwest Airlines
WN 814
11:00
Chicago, Chicago Midway International Airport (MDW)
Mon, 23 nov
2h 5min
Direct
13:05
New York, LaGuardia Airport (LGA)
Mon, 23 nov
223 NZ$
Southwest Airlines
WN 4731
01:40
Chicago, Chicago Midway International Airport (MDW)
Tue, 19 jan
2h
Direct
03:40
New York, LaGuardia Airport (LGA)
Tue, 19 jan
236 NZ$

Low price calendar

September 2026
Price chart (September 2026)
min: 145 NZ$ · max: 240 NZ$
01.09.2026 — no data 02.09.2026 — no data 03.09.2026 — no data 04.09.2026 — no data 05.09.2026 — no data 06.09.2026 — no data 07.09.2026 — no data 08.09.2026 — no data 09.09.2026 — no data 10.09.2026 — no data 11.09.2026 — no data 12.09.2026 — 187 NZ$ 13.09.2026 — 145 NZ$ 14.09.2026 — 182 NZ$ 15.09.2026 — 225 NZ$ 16.09.2026 — 210 NZ$ 17.09.2026 — 226 NZ$ 18.09.2026 — 224 NZ$ 19.09.2026 — 186 NZ$ 20.09.2026 — 204 NZ$ 21.09.2026 — 228 NZ$ 22.09.2026 — 220 NZ$ 23.09.2026 — 194 NZ$ 24.09.2026 — 240 NZ$ 25.09.2026 — 204 NZ$ 26.09.2026 — 235 NZ$ 27.09.2026 — 195 NZ$ 28.09.2026 — 234 NZ$ 29.09.2026 — 220 NZ$ 30.09.2026 — 177 NZ$ 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30
Mon
Tue
Wed
Thu
Fri
Sat
Sun
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187 NZ$
13
Good deal
145 NZ$
14
Good deal
182 NZ$
15
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225 NZ$
16
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210 NZ$
17
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226 NZ$
18
placeholder
224 NZ$
19
Good deal
186 NZ$
20
placeholder
204 NZ$
21
placeholder
228 NZ$
22
placeholder
220 NZ$
23
placeholder
194 NZ$
24
placeholder
240 NZ$
25
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204 NZ$
26
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235 NZ$
27
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195 NZ$
28
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234 NZ$
29
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220 NZ$
30
Good deal
177 NZ$

Popular Southwest Airlines flights Chicago – New York

All →
Flight Departure days Price from
WN4236 Tue NZ$133
WN4797 Sat NZ$133
WN2905 MonTueThuFriSun NZ$140
WN2013 Mon NZ$144
WN921 ThuFri NZ$146
WN2745 Wed NZ$173
WN3948 Mon NZ$182
WN258 Tue NZ$186
WN487 Sat NZ$188
WN814 MonFri NZ$197

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
NZ$37
CHI
Chicago — Orlando
United States → United States
MCO
from
NZ$37
CHI
Chicago — Atlanta
United States → United States
ATL
from
NZ$38
CHI
Chicago — Houston
United States → United States
IAH
from
NZ$38
CHI
Chicago — Houston
United States → United States
HOU
from
NZ$38
CHI
Chicago — Denver
United States → United States
DEN
from
NZ$41
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
NZ$42
CHI
Chicago — Miami
United States → United States
MIA
from
NZ$43

Popular destinations to New York

All →
ORL
Orlando — New York
United States → United States
NYC
from
NZ$31
ATL
Atlanta — New York
United States → United States
NYC
from
NZ$38
FLL
Fort Lauderdale — New York
United States → United States
NYC
from
NZ$50
MIA
Miami — New York
United States → United States
NYC
from
NZ$60
DFW
Dallas — New York
United States → United States
NYC
from
NZ$94
TPA
Tampa — New York
United States → United States
NYC
from
NZ$96
RDU
Raleigh — New York
United States → United States
NYC
from
NZ$107
LAX
Los Angeles — New York
United States → United States
NYC
from
NZ$119

Flight statistics Chicago – New York, Southwest Airlines

We gathered interesting facts about the flight for you

Cheapest flight

WN 4236

NZ$133

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
NZ$146
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
NZ$186
Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sat
Price from
NZ$191
United Airlines
United Airlines
Tue, Wed, Thu, Fri, Sat, Sun
Price from
NZ$191

Internet abroad

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All plans

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30

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NZ$15

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2 GB

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15

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NZ$22

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5 GB

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30

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NZ$24

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NZ$28

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30

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NZ$39

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Chicago – New York costs NZ$133, 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.