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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 🔥 Hot deal
10:00
New York, Ла Гуардиа (LGA)
Tue, 15 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Tue, 15 sep
79 $
Southwest Airlines
WN 2714
01:35
New York, Ла Гуардиа (LGA)
Wed, 16 sep
2h 20min
Direct
03:55
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
169 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Wed, 16 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
127 $
Frontier Airlines
F9 3287
10:15
New York, Ла Гуардиа (LGA)
Wed, 16 sep
12h 36min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
125 $
Frontier Airlines
F9 4601 🔥 Hot deal
15:35
New York, Ньюарк Либерти (EWR)
Wed, 16 sep
7h 16min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
79 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Wed, 16 sep
5h 51min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
120 $
Southwest Airlines
WN 2414
17:25
New York, Ла Гуардиа (LGA)
Wed, 16 sep
2h 20min
Direct
19:45
Chicago, Чикаго-Мидвей (MDW)
Wed, 16 sep
79 $
Southwest Airlines
WN 2714
01:35
New York, Ла Гуардиа (LGA)
Thu, 17 sep
2h 20min
Direct
03:55
Chicago, Чикаго-Мидвей (MDW)
Thu, 17 sep
83 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Thu, 17 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Thu, 17 sep
159 $
Frontier Airlines
F9 3287
10:15
New York, Ла Гуардиа (LGA)
Thu, 17 sep
12h 31min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Thu, 17 sep
118 $
Southwest Airlines
WN 2412
11:25
New York, Ла Гуардиа (LGA)
Thu, 17 sep
2h 20min
Direct
13:45
Chicago, Чикаго-Мидвей (MDW)
Thu, 17 sep
115 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Thu, 17 sep
5h 46min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Thu, 17 sep
141 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Fri, 18 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Fri, 18 sep
112 $
Southwest Airlines
WN 4003
19:00
New York, Ла Гуардиа (LGA)
Fri, 18 sep
5h 45min
1 stop
00:45
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep +1
134 $
Frontier Airlines
F9 3453
20:55
New York, Ла Гуардиа (LGA)
Fri, 18 sep
7h 49min
1 stop
04:44
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep +1
141 $
Southwest Airlines
WN 4889
00:55
New York, Ла Гуардиа (LGA)
Sat, 19 sep
2h 25min
Direct
03:20
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
107 $
Southwest Airlines
WN 4240
01:05
New York, Ла Гуардиа (LGA)
Sat, 19 sep
13h 15min
1 stop
14:20
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
165 $
Southwest Airlines
WN 2412
11:35
New York, Ла Гуардиа (LGA)
Sat, 19 sep
2h 20min
Direct
13:55
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
79 $
Southwest Airlines
WN 2413
13:40
New York, Ла Гуардиа (LGA)
Sat, 19 sep
2h 25min
Direct
16:05
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
109 $
Frontier Airlines
F9 4601
15:35
New York, Ньюарк Либерти (EWR)
Sat, 19 sep
7h 16min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
140 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Sat, 19 sep
5h 51min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
123 $
Southwest Airlines
WN 2414
18:00
New York, Ла Гуардиа (LGA)
Sat, 19 sep
2h 20min
Direct
20:20
Chicago, Чикаго-Мидвей (MDW)
Sat, 19 sep
145 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Sun, 20 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Sun, 20 sep
186 $
Southwest Airlines
WN 2412
11:20
New York, Ла Гуардиа (LGA)
Sun, 20 sep
2h 20min
Direct
13:40
Chicago, Чикаго-Мидвей (MDW)
Sun, 20 sep
109 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Mon, 21 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Mon, 21 sep
156 $
Frontier Airlines
F9 3287
10:15
New York, Ла Гуардиа (LGA)
Mon, 21 sep
12h 36min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Mon, 21 sep
145 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Mon, 21 sep
5h 51min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Mon, 21 sep
138 $
Frontier Airlines
F9 3453
20:55
New York, Ла Гуардиа (LGA)
Mon, 21 sep
7h 49min
1 stop
04:44
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep +1
158 $
Southwest Airlines
WN 4889
00:55
New York, Ла Гуардиа (LGA)
Tue, 22 sep
2h 25min
Direct
03:20
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
175 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Tue, 22 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
80 $
Frontier Airlines
F9 4601
15:35
New York, Ньюарк Либерти (EWR)
Tue, 22 sep
7h 11min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
141 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Tue, 22 sep
5h 46min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Tue, 22 sep
119 $
Southwest Airlines
WN 4741
21:40
New York, Ла Гуардиа (LGA)
Tue, 22 sep
2h 30min
Direct
00:10
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep +1
79 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Wed, 23 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep
80 $
Frontier Airlines
F9 4601
15:35
New York, Ньюарк Либерти (EWR)
Wed, 23 sep
7h 16min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep
128 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Wed, 23 sep
5h 51min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep
116 $
Southwest Airlines
WN 3058
20:10
New York, Ла Гуардиа (LGA)
Wed, 23 sep
2h 30min
Direct
22:40
Chicago, Чикаго-Мидвей (MDW)
Wed, 23 sep
110 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Thu, 24 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Thu, 24 sep
129 $
Frontier Airlines
F9 3287
10:15
New York, Ла Гуардиа (LGA)
Thu, 24 sep
12h 31min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Thu, 24 sep
126 $
Frontier Airlines
F9 4601
15:35
New York, Ньюарк Либерти (EWR)
Thu, 24 sep
7h 11min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Thu, 24 sep
128 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Thu, 24 sep
5h 46min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Thu, 24 sep
119 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Fri, 25 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Fri, 25 sep
144 $
Southwest Airlines
WN 4889
00:55
New York, Ла Гуардиа (LGA)
Sat, 26 sep
2h 25min
Direct
03:20
Chicago, Чикаго-Мидвей (MDW)
Sat, 26 sep
113 $
Frontier Airlines
F9 3287
10:15
New York, Ла Гуардиа (LGA)
Sat, 26 sep
12h 36min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Sat, 26 sep
145 $
Frontier Airlines
F9 4731
17:00
New York, Кеннеди (JFK)
Sat, 26 sep
5h 51min
1 stop
22:51
Chicago, Чикаго-Мидвей (MDW)
Sat, 26 sep
123 $
Southwest Airlines
WN 4741
21:50
New York, Ла Гуардиа (LGA)
Sat, 26 sep
2h 30min
Direct
00:20
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep +1
126 $
Frontier Airlines
F9 1659
09:55
New York, Ньюарк Либерти (EWR)
Sun, 27 sep
42h 49min
2 stops
04:44
Chicago, Чикаго-Мидвей (MDW)
Tue, 29 sep +1
157 $
Southwest Airlines
WN 2411
10:00
New York, Ла Гуардиа (LGA)
Sun, 27 sep
2h 15min
Direct
12:15
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
146 $
Frontier Airlines
F9 4601
15:35
New York, Ньюарк Либерти (EWR)
Sun, 27 sep
7h 11min
1 stop
22:46
Chicago, Чикаго-Мидвей (MDW)
Sun, 27 sep
96 $
Southwest Airlines
WN 4889
00:55
New York, Ла Гуардиа (LGA)
Tue, 29 sep
2h 25min
Direct
03:20
Chicago, Чикаго-Мидвей (MDW)
Tue, 29 sep
131 $

Low price calendar

September 2026
Price chart (September 2026)
min: 75 $ · max: 141 $
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119 $
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130 $
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141 $
18
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112 $
19
Good deal
109 $
20
Good deal
109 $
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138 $
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141 $
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110 $
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128 $
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113 $
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Good deal
96 $
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Good deal
75 $
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119 $

Cheap flights New York to Chicago Midway International Airport

Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$75
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
$96

Popular destinations from New York

All →
NYC
New York — Orlando
United States → United States
ORL
from
$18
NYC
New York — Atlanta
United States → United States
ATL
from
$20
NYC
New York — Cleveland
United States → United States
CLE
from
$22
NYC
New York — Chicago
United States → United States
CHI
from
$22
NYC
New York — Dallas
United States → United States
DFW
from
$26
NYC
New York — Miami
United States → United States
MIA
from
$27
NYC
New York — Fort Lauderdale
United States → United States
FLL
from
$27
NYC
New York — Detroit
United States → United States
DTT
from
$28

Popular destinations to Chicago Midway International Airport

All →
ATL
Atlanta — Chicago
United States → United States
MDW
from
$37
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
$55
HOU
Houston — Chicago
United States → United States
MDW
from
$60
DFW
Dallas — Chicago
United States → United States
MDW
from
$70
PHL
Philadelphia — Chicago
United States → United States
MDW
from
$71
TPA
Tampa — Chicago
United States → United States
MDW
from
$74
MIA
Miami — Chicago
United States → United States
MDW
from
$75
DEN
Denver — Chicago
United States → United States
MDW
from
$77

Cheap flights New York to Chicago Midway International Airport

Interesting facts about the route

Flight time

2h 45min

Distance

1 163 km

Average price

$130

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

$9

Buy

change

2 GB

data

15

days

$13

Buy

change

5 GB

data

30

days

$14

Buy

change

3 GB

data

30

days

$16

Buy

change

5 GB

data

30

days

$23

Buy

Frequently Asked Questions

The average ticket price New York Chicago Midway International Airport is $130. The cheapest ticket costs $79, 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.