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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)
Sun, 20 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
£139
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
£82
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
£117
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
£108
Frontier Airlines
F9 4601 🔥 Hot deal
15:35
New York, Newark Liberty International Airport (EWR)
Mon, 21 sep
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
£98
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
£104
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
£119
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
£131
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
£60
Frontier Airlines
F9 4601 🔥 Hot deal
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
£98
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
£89
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
£59
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
£60
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
£121
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
£87
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
£82
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
£127
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
£94
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
£96
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
£89
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
£108
Southwest Airlines
WN 4003
19:00
New York, LaGuardia Airport (LGA)
Fri, 25 sep
5h 45min
1 stop
00:45
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep +1
£133
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
£85
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
£109
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
£114
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
£92
Southwest Airlines
WN 2414
18:00
New York, LaGuardia Airport (LGA)
Sat, 26 sep
2h 20min
Direct
20:20
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
£129
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
£115
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
£118
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
£110
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
£72
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
£98
Southwest Airlines
WN 2411
10:00
New York, LaGuardia Airport (LGA)
Tue, 29 sep
2h 15min
Direct
12:15
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
£126
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Tue, 29 sep
7h 11min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
£101
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Tue, 29 sep
5h 46min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
£89
Southwest Airlines
WN 2414
17:25
New York, LaGuardia Airport (LGA)
Tue, 29 sep
2h 20min
Direct
19:45
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
£60
Southwest Airlines
WN 2714
01:35
New York, LaGuardia Airport (LGA)
Wed, 30 sep
2h 20min
Direct
03:55
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
£60
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Wed, 30 sep
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
£89
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Wed, 30 sep
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
£89
Southwest Airlines
WN 2714
01:35
New York, LaGuardia Airport (LGA)
Thu, 1 oct
2h 20min
Direct
03:55
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
£102
Southwest Airlines
WN 2542
14:55
New York, LaGuardia Airport (LGA)
Thu, 1 oct
2h 20min
Direct
17:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
£61
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Thu, 1 oct
7h 11min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
£71
Frontier Airlines
F9 3453
20:55
New York, LaGuardia Airport (LGA)
Thu, 1 oct
7h 49min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 2 oct +1
£125
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Fri, 2 oct
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Fri, 2 oct
£102
Frontier Airlines
F9 3453
20:55
New York, LaGuardia Airport (LGA)
Fri, 2 oct
7h 49min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct +1
£95
Southwest Airlines
WN 2912
10:15
New York, LaGuardia Airport (LGA)
Sat, 3 oct
2h 30min
Direct
12:45
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
£114
Southwest Airlines
WN 2509
13:25
New York, LaGuardia Airport (LGA)
Sat, 3 oct
2h 30min
Direct
15:55
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
£85
Frontier Airlines
F9 4601
15:35
New York, Newark Liberty International Airport (EWR)
Sat, 3 oct
7h 16min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
£104
Frontier Airlines
F9 4731
17:00
New York, John F. Kennedy International Airport (JFK)
Sat, 3 oct
5h 51min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
£87
Southwest Airlines
WN 2913
10:00
New York, LaGuardia Airport (LGA)
Sun, 4 oct
2h 30min
Direct
12:30
Chicago, Chicago Midway International Airport (MDW)
Sun, 4 oct
£112

Low price calendar

September 2026
Price chart (September 2026)
min: £56 · max: £105
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£82
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£104
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£82
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£96
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£85
27
Good deal
£72
28
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Good deal
£56
30
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£89

Cheap flights New York to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
£68
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
£71

Popular destinations from New York

All →
NYC
New York — Orlando
United States → United States
ORL
from
£13
NYC
New York — Atlanta
United States → United States
ATL
from
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NYC
New York — Cleveland
United States → United States
CLE
from
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NYC
New York — Chicago
United States → United States
CHI
from
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New York — Dallas
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DFW
from
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NYC
New York — Miami
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from
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New York — Detroit
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DTT
from
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Popular destinations to Chicago Midway International Airport

All →
ATL
Atlanta — Chicago
United States → United States
MDW
from
£28
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
£41
HOU
Houston — Chicago
United States → United States
MDW
from
£45
DFW
Dallas — Chicago
United States → United States
MDW
from
£53
PHL
Philadelphia — Chicago
United States → United States
MDW
from
£53
ORL
Orlando — Chicago
United States → United States
MDW
from
£54
TPA
Tampa — Chicago
United States → United States
MDW
from
£55
MIA
Miami — Chicago
United States → United States
MDW
from
£56

Cheap flights New York to Chicago Midway International Airport

Interesting facts about the route

Flight time

2h 40min

Distance

1 163 km

Average price

£98

Most frequent flight

WN 834

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

£7

Buy

change

2 GB

data

15

days

£9

Buy

change

5 GB

data

30

days

£10

Buy

change

3 GB

data

30

days

£12

Buy

change

5 GB

data

30

days

£17

Buy

Frequently Asked Questions

The average ticket price New York Chicago Midway International Airport is £98. The cheapest ticket costs £59, operated by Southwest Airlines, flight 4741, departing New York on 22 September at 21:40, arriving Chicago Midway International Airport on 23 September at 00:10.
The average flight time is 2 hours 30 minutes.The fastest flight takes 2 hours 15 minutes, flight 2411operated by Southwest Airlines, departing New York on 20 September at 10:00, arriving Chicago Midway International Airport on 20 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.