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Cheap flights New York to Chicago Midway International Airport

1 passenger, economy

Cheap flights New York to Chicago Midway International Airport

Compare prices, duration and stops

Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Wed, 16 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
161 S$
Frontier Airlines
F9 3287
10:15
New York, LaGuardia Airport (LGA)
Wed, 16 sep
12h 36min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
159 S$
Frontier Airlines
F9 4601 🔥 Hot deal
15:35
New York, Newark Liberty International Airport (EWR)
Wed, 16 sep
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
100 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Wed, 16 sep
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
153 S$
Southwest Airlines
WN 2414
17:25
New York, LaGuardia Airport (LGA)
Wed, 16 sep
2h 20min
Direct
19:45
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
101 S$
Southwest Airlines
WN 2714
01:35
New York, LaGuardia Airport (LGA)
Thu, 17 sep
2h 20min
Direct
03:55
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
105 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Thu, 17 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
202 S$
Frontier Airlines
F9 3287
10:15
New York, LaGuardia Airport (LGA)
Thu, 17 sep
12h 31min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
150 S$
Southwest Airlines
WN 2412
11:25
New York, LaGuardia Airport (LGA)
Thu, 17 sep
2h 20min
Direct
13:45
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
146 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Thu, 17 sep
5h 46min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
179 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Fri, 18 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep
142 S$
Southwest Airlines
WN 4003
19:00
New York, LaGuardia Airport (LGA)
Fri, 18 sep
5h 45min
1 stop
00:45
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep +1
170 S$
Frontier Airlines
F9 3453
20:55
New York, LaGuardia Airport (LGA)
Fri, 18 sep
7h 49min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep +1
179 S$
Southwest Airlines
WN 4889
00:55
New York, LaGuardia Airport (LGA)
Sat, 19 sep
2h 25min
Direct
03:20
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
137 S$
Southwest Airlines
WN 4240
01:05
New York, LaGuardia Airport (LGA)
Sat, 19 sep
13h 15min
1 stop
14:20
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
210 S$
Southwest Airlines
WN 2412
11:35
New York, LaGuardia Airport (LGA)
Sat, 19 sep
2h 20min
Direct
13:55
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
101 S$
Southwest Airlines
WN 2413
13:40
New York, LaGuardia Airport (LGA)
Sat, 19 sep
2h 25min
Direct
16:05
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
139 S$
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Sat, 19 sep
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
178 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Sat, 19 sep
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
157 S$
Southwest Airlines
WN 2414
18:00
New York, LaGuardia Airport (LGA)
Sat, 19 sep
2h 20min
Direct
20:20
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
185 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Sun, 20 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
237 S$
Southwest Airlines
WN 2412
11:20
New York, LaGuardia Airport (LGA)
Sun, 20 sep
2h 20min
Direct
13:40
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
139 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Mon, 21 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
199 S$
Frontier Airlines
F9 3287
10:15
New York, LaGuardia Airport (LGA)
Mon, 21 sep
12h 36min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
184 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Mon, 21 sep
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
176 S$
Frontier Airlines
F9 3453
20:55
New York, LaGuardia Airport (LGA)
Mon, 21 sep
7h 49min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep +1
201 S$
Southwest Airlines
WN 4889
00:55
New York, LaGuardia Airport (LGA)
Tue, 22 sep
2h 25min
Direct
03:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
222 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Tue, 22 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
102 S$
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Tue, 22 sep
7h 11min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
179 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Tue, 22 sep
5h 46min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
151 S$
Southwest Airlines
WN 4741
21:40
New York, LaGuardia Airport (LGA)
Tue, 22 sep
2h 30min
Direct
00:10
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep +1
101 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Wed, 23 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
101 S$
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Wed, 23 sep
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
179 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Wed, 23 sep
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
147 S$
Southwest Airlines
WN 3058
20:10
New York, LaGuardia Airport (LGA)
Wed, 23 sep
2h 30min
Direct
22:40
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
140 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Thu, 24 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
164 S$
Frontier Airlines
F9 3287
10:15
New York, LaGuardia Airport (LGA)
Thu, 24 sep
12h 31min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
160 S$
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Thu, 24 sep
7h 11min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
162 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Thu, 24 sep
5h 46min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
151 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Fri, 25 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 sep
184 S$
Southwest Airlines
WN 4889
00:55
New York, LaGuardia Airport (LGA)
Sat, 26 sep
2h 25min
Direct
03:20
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
144 S$
Frontier Airlines
F9 3287
10:15
New York, LaGuardia Airport (LGA)
Sat, 26 sep
12h 36min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
184 S$
Southwest Airlines
WN 2412
11:35
New York, LaGuardia Airport (LGA)
Sat, 26 sep
2h 20min
Direct
13:55
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
193 S$
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Sat, 26 sep
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
157 S$
Southwest Airlines
WN 4741
21:50
New York, LaGuardia Airport (LGA)
Sat, 26 sep
2h 30min
Direct
00:20
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep +1
160 S$
Frontier Airlines
F9 1659
09:55
New York, Newark Liberty International Airport (EWR)
Sun, 27 sep
42h 49min
2 stops
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep +1
200 S$
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Sun, 27 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
186 S$
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Sun, 27 sep
7h 11min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
122 S$
Southwest Airlines
WN 4889
00:55
New York, LaGuardia Airport (LGA)
Tue, 29 sep
2h 25min
Direct
03:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
167 S$
Southwest Airlines
WN 2411 Best price
10:00
New York, LaGuardia Airport (LGA)
Tue, 29 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
96 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 96 S$ · max: 179 S$
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Tue
Wed
Thu
Fri
Sat
Sun
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165 S$
17
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179 S$
18
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142 S$
19
Good deal
139 S$
20
Good deal
139 S$
21
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176 S$
22
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179 S$
23
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140 S$
24
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162 S$
25
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26
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144 S$
27
Good deal
122 S$
28
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29
Good deal
96 S$
30
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152 S$

Cheap flights New York to Chicago Midway International Airport

Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$96
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$122

Popular destinations from New York

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CLE
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CHI
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Popular destinations to Chicago Midway International Airport

All →
ATL
Atlanta — Chicago
United States → United States
MDW
from
S$47
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
S$69
HOU
Houston — Chicago
United States → United States
MDW
from
S$76
DFW
Dallas — Chicago
United States → United States
MDW
from
S$89
PHL
Philadelphia — Chicago
United States → United States
MDW
from
S$90
ORL
Orlando — Chicago
United States → United States
MDW
from
S$92
TPA
Tampa — Chicago
United States → United States
MDW
from
S$94
MIA
Miami — Chicago
United States → United States
MDW
from
S$96

Cheap flights New York to Chicago Midway International Airport

Interesting facts about the route

Flight time

2h 40min

Distance

1 163 km

Average price

S$167

Most frequent flight

WN 2411

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

S$11

Buy

change

2 GB

data

15

days

S$16

Buy

change

5 GB

data

30

days

S$18

Buy

change

3 GB

data

30

days

S$20

Buy

change

5 GB

data

30

days

S$29

Buy

Frequently Asked Questions

The average ticket price New York Chicago Midway International Airport is S$167. The cheapest ticket costs S$101, operated by Southwest Airlines, flight 2414, departing New York on 16 September at 17:25, arriving Chicago Midway International Airport on 16 September at 19:45.
The average flight time is 2 hours 25 minutes. The fastest flight takes 2 hours 15 minutes, flight 2411 operated by Southwest Airlines, departing New York on 16 September at 10:00, arriving Chicago Midway International Airport on 16 September at 12:15.
Flights on the New York - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from New York to Chicago Midway International Airport is 1163 km.