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Find Deals on Flights from New York to Chicago Midway (NYC - MDW)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from New York to Chicago Midway

(Round-trip)
Depart: Tue Jul 21 2015 Return: Wed Jul 22 2015 Trip spans 2 days
Delta
Delta
JFK
9:59a
MDW
2:53p
4h 54m
1 stop
MDW
2:30a
JFK
9:59a
7h 29m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Sep 22 2015 Trip spans 35 days
Delta
Delta
JFK
4:20a
MDW
11:44a
7h 24m
1 stop
MDW
2:00a
JFK
7:28a
5h 28m
1 stop
Depart: Sat Aug 22 2015 Return: Sun Aug 23 2015 Trip spans 2 days
Delta
Delta
JFK
7:00a
MDW
1:43p
6h 43m
1 stop
MDW
3:45a
JFK
9:59a
6h 14m
1 stop
Depart: Mon Aug 24 2015 Return: Mon Aug 31 2015 Trip spans 8 days
Delta
Delta
JFK
7:00a
MDW
1:44p
6h 44m
1 stop
MDW
9:40a
JFK
6:10p
8h 30m
1 stop
Depart: Wed Aug 26 2015 Return: Mon Aug 31 2015 Trip spans 6 days
Delta
Delta
JFK
2:30a
MDW
8:44a
6h 14m
1 stop
MDW
5:06a
JFK
9:59a
4h 53m
1 stop
Depart: Thu Aug 27 2015 Return: Mon Aug 31 2015 Trip spans 5 days
Delta
Delta
JFK
9:00a
MDW
5:18p
8h 18m
1 stop
MDW
5:06a
JFK
9:59a
4h 53m
1 stop
Depart: Fri Aug 28 2015 Return: Mon Aug 31 2015 Trip spans 4 days
Delta
Delta
JFK
9:00a
MDW
5:18p
8h 18m
1 stop
MDW
5:06a
JFK
9:59a
4h 53m
1 stop
Depart: Sat Aug 29 2015 Return: Mon Aug 31 2015 Trip spans 3 days
Delta
Delta
JFK
3:45a
MDW
11:51a
8h 06m
1 stop
MDW
5:06a
JFK
9:59a
4h 53m
1 stop
Depart: Mon Aug 31 2015 Return: Tue Sep 1 2015 Trip spans 2 days
Delta
Delta
JFK
9:00a
MDW
2:22p
5h 22m
1 stop
MDW
2:00a
JFK
7:29a
5h 29m
1 stop
Depart: Tue Sep 1 2015 Return: Sat Sep 12 2015 Trip spans 12 days
Delta
Delta
JFK
12:26p
MDW
6:09p
5h 43m
1 stop
MDW
2:00a
JFK
7:29a
5h 29m
1 stop
Depart: Wed Sep 2 2015 Return: Sat Sep 12 2015 Trip spans 11 days
Delta
Delta
JFK
10:30a
MDW
2:54p
4h 24m
1 stop
MDW
2:00a
JFK
7:29a
5h 29m
1 stop
Depart: Sat Sep 5 2015 Return: Tue Sep 8 2015 Trip spans 4 days
Delta
Delta
JFK
11:30a
MDW
5:10p
5h 40m
1 stop
MDW
7:06a
JFK
12:28p
5h 22m
1 stop
Depart: Sun Sep 6 2015 Return: Tue Sep 8 2015 Trip spans 3 days
Delta
Delta
JFK
2:29a
MDW
8:49a
6h 20m
1 stop
MDW
5:17a
JFK
10:48a
5h 31m
1 stop
Depart: Mon Sep 7 2015 Return: Tue Sep 8 2015 Trip spans 2 days
Delta
Delta
JFK
5:10a
MDW
9:23a
4h 13m
1 stop
MDW
7:06a
JFK
12:28p
5h 22m
1 stop
Depart: Tue Sep 8 2015 Return: Tue Oct 13 2015 Trip spans 36 days
Delta
Delta
JFK
5:10a
MDW
9:23a
4h 13m
1 stop
MDW
8:36a
JFK
2:28p
5h 52m
1 stop
Depart: Wed Sep 9 2015 Return: Sat Sep 12 2015 Trip spans 4 days
Delta
Delta
JFK
5:10a
MDW
9:23a
4h 13m
1 stop
MDW
2:00a
JFK
7:29a
5h 29m
1 stop
Depart: Thu Sep 10 2015 Return: Sat Sep 19 2015 Trip spans 10 days
Delta
Delta
JFK
5:10a
MDW
9:23a
4h 13m
1 stop
MDW
7:07a
JFK
12:30p
5h 23m
1 stop
Depart: Thu Aug 20 2015 Return: Tue Aug 25 2015 Trip spans 6 days
Delta
Delta
EWR
3:15a
MDW
9:23a
6h 08m
1 stop
MDW
3:10a
EWR
9:55a
6h 45m
1 stop
Depart: Mon Aug 17 2015 Return: Tue Aug 18 2015 Trip spans 2 days
Sun Country Air
Sun Country Air
JFK
3:15a
MDW
5:45p
14h 30m
1 stop
MDW
4:00a
JFK
3:05p
11h 05m
1 stop
Depart: Sun Sep 27 2015 Return: Sat Oct 10 2015 Trip spans 14 days
Delta
Delta
LGA
4:59a
MDW
9:23a
4h 24m
1 stop
MDW
8:36a
LGA
12:10p
3h 34m
1 stop
Select an airline:  Southwest
Direct flights NYC to MDW on Southwest
Flight # Depart LGA Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
2073 6:00 am 7:20 am Aug 9 - Sep 4
838 6:00 am 7:20 am Jul 10 - Aug 7
2250 6:05 am 7:25 am Jul 11 - Aug 8
2814 9:20 am 10:45 am Jun 27 - Aug 1
2088 9:30 am 11:05 am Aug 10 - Sep 4
2814 9:30 am 11:00 am Aug 8 - Aug 8
3653 9:30 am 11:05 am Aug 9 - Aug 30
806 9:30 am 11:05 am Jul 10 - Aug 7
694 11:10 am 12:40 pm Jul 12 - Aug 7
483 11:25 am 1:00 pm Aug 9 - Sep 4
2842 12:40 pm 2:15 pm Jul 18 - Aug 1
2842 12:40 pm 2:15 pm Aug 8 - Aug 8
381 3:15 pm 4:45 pm Aug 9 - Sep 4
633 3:25 pm 5:05 pm Jul 10 - Aug 7
4254 4:15 pm 5:50 pm Jul 11 - Aug 1
3554 5:35 pm 7:10 pm Aug 8 - Aug 8
1057 5:50 pm 7:20 pm Aug 9 - Aug 30
2743 5:50 pm 7:25 pm Aug 10 - Aug 28
163 5:55 pm 7:30 pm Jul 10 - Aug 7
1576 6:55 pm 8:30 pm Aug 9 - Sep 4
4535 6:55 pm 8:30 pm Jul 11 - Aug 1
5288 6:55 pm 8:30 pm Aug 8 - Aug 8
434 7:40 pm 9:15 pm Jul 10 - Aug 7
402 8:50 pm 10:15 pm Jul 11 - Aug 1
402 8:55 pm 10:20 pm Aug 8 - Aug 8
902 8:55 pm 10:20 pm Jul 10 - Aug 7
935 8:55 pm 10:25 pm Aug 9 - Oct 30
Flight # Depart EWR Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
769 6:00 am 7:15 am Aug 8 - Aug 8
769 6:00 am 7:15 am Jul 10 - Aug 7
769 6:00 am 7:15 am Jul 11 - Aug 1
1571 6:15 am 7:35 am Aug 10 - Sep 4
1591 9:35 am 10:55 am Aug 9 - Aug 30
1826 9:35 am 10:55 am Aug 10 - Sep 4
824 9:35 am 10:55 am Jun 28 - Aug 7
1211 12:00 pm 1:15 pm Jul 18 - Aug 8
700 12:10 pm 1:25 pm Jul 10 - Aug 7
700 12:10 pm 1:25 pm Jun 28 - Aug 2
1586 12:25 pm 1:50 pm Aug 9 - Aug 30
1586 12:25 pm 1:50 pm Aug 10 - Sep 4
1292 4:30 pm 5:55 pm Jul 10 - Aug 7
1582 4:30 pm 5:55 pm Aug 9 - Sep 4
2563 5:55 pm 7:40 pm Jul 11 - Aug 8
2460 6:25 pm 7:55 pm Aug 9 - Sep 4
916 6:25 pm 8:05 pm Aug 3 - Aug 7
916 6:25 pm 8:05 pm Jul 10 - Jul 31
916 6:25 pm 8:05 pm Jun 28 - Aug 2
976 8:50 pm 10:15 pm Aug 9 - Sep 4
3582 8:55 pm 10:25 pm Jun 28 - Aug 7
Airports
Origin

New York
only $514
only $230
Newark
$248
Destination

Chicago
$230