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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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: Fri Oct 2 2015 Return: Thu Oct 8 2015 Trip spans 7 days
Southwest
Southwest
LGA
4:55p
MDW
7:25p
2h 30m
nonstop
MDW
1:50a
LGA
3:55a
2h 05m
nonstop
Depart: Wed Sep 30 2015 Return: Fri Oct 2 2015 Trip spans 3 days
Southwest
Southwest
EWR
4:50p
MDW
7:15p
2h 25m
nonstop
MDW
2:05a
EWR
4:00a
1h 55m
nonstop
Depart: Fri Oct 16 2015 Return: Mon Oct 19 2015 Trip spans 4 days
Southwest
Southwest
EWR
2:05a
MDW
4:25a
2h 20m
nonstop
MDW
1:10p
EWR
3:15p
2h 05m
nonstop
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
5:17a
JFK
10:48a
5h 31m
1 stop
Depart: Tue Aug 25 2015 Return: Mon Aug 31 2015 Trip spans 7 days
Delta
Delta
EWR
12:54p
MDW
5:27p
4h 33m
1 stop
MDW
12:33p
EWR
4:29p
3h 56m
1 stop
Depart: Wed Aug 26 2015 Return: Mon Aug 31 2015 Trip spans 6 days
Delta
Delta
EWR
9:00a
MDW
2:22p
5h 22m
1 stop
MDW
12:33p
EWR
4:29p
3h 56m
1 stop
Depart: Thu Aug 27 2015 Return: Mon Aug 31 2015 Trip spans 5 days
Delta
Delta
EWR
2:10a
MDW
7:25a
5h 15m
1 stop
MDW
12:33p
EWR
4:29p
3h 56m
1 stop
Depart: Sat Aug 29 2015 Return: Tue Sep 1 2015 Trip spans 4 days
Delta
Delta
EWR
9:00a
MDW
2:43p
5h 43m
1 stop
MDW
2:35p
EWR
6:29p
3h 54m
1 stop
Depart: Sun Aug 30 2015 Return: Tue Sep 1 2015 Trip spans 3 days
Delta
Delta
EWR
3:15a
MDW
9:23a
6h 08m
1 stop
MDW
2:35p
EWR
6:29p
3h 54m
1 stop
Depart: Tue Sep 1 2015 Return: Tue Sep 29 2015 Trip spans 29 days
Delta
Delta
EWR
2:00a
MDW
5:42a
3h 42m
1 stop
MDW
2:35p
EWR
6:29p
3h 54m
1 stop
Depart: Wed Sep 2 2015 Return: Tue Sep 8 2015 Trip spans 7 days
Delta
Delta
EWR
2:00a
MDW
5:42a
3h 42m
1 stop
MDW
3:00a
EWR
7:07a
4h 07m
1 stop
Depart: Thu Sep 3 2015 Return: Tue Sep 8 2015 Trip spans 6 days
Delta
Delta
EWR
2:00a
MDW
5:42a
3h 42m
1 stop
MDW
3:00a
EWR
7:07a
4h 07m
1 stop
Depart: Sun Sep 6 2015 Return: Tue Sep 8 2015 Trip spans 3 days
Delta
Delta
EWR
8:49a
MDW
12:58p
4h 09m
1 stop
MDW
3:00a
EWR
7:07a
4h 07m
1 stop
Depart: Mon Sep 7 2015 Return: Tue Sep 8 2015 Trip spans 2 days
Delta
Delta
EWR
2:00a
MDW
5:42a
3h 42m
1 stop
MDW
5:17a
EWR
9:01a
3h 44m
1 stop
Depart: Tue Sep 8 2015 Return: Mon Sep 14 2015 Trip spans 7 days
Delta
Delta
EWR
3:29a
MDW
9:23a
5h 54m
1 stop
MDW
2:35p
EWR
6:29p
3h 54m
1 stop
Depart: Wed Sep 9 2015 Return: Sat Sep 12 2015 Trip spans 4 days
Delta
Delta
EWR
2:00a
MDW
5:42a
3h 42m
1 stop
MDW
1:59p
EWR
7:10p
5h 11m
1 stop
Depart: Thu Sep 10 2015 Return: Sat Sep 12 2015 Trip spans 3 days
Delta
Delta
EWR
4:45a
MDW
10:15a
5h 30m
1 stop
MDW
11:20a
EWR
4:42p
5h 22m
1 stop
Depart: Fri Sep 11 2015 Return: Sat Sep 12 2015 Trip spans 2 days
Delta
Delta
EWR
2:00a
MDW
5:42a
3h 42m
1 stop
MDW
12:35p
EWR
4:29p
3h 54m
1 stop
Depart: Sat Sep 12 2015 Return: Mon Sep 14 2015 Trip spans 3 days
Delta
Delta
EWR
7:45a
MDW
2:22p
6h 37m
1 stop
MDW
2:35p
EWR
6:29p
3h 54m
1 stop
Depart: Mon Dec 21 2015 Return: Tue Dec 29 2015 Trip spans 9 days
Delta
Delta
LGA
4:00a
MDW
8:19a
4h 19m
1 stop
MDW
7:40a
LGA
11:09a
3h 29m
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
1653 6:00 am 7:20 am Sep 7 - Sep 7
2073 6:00 am 7:20 am Aug 9 - Sep 4
2073 6:00 am 7:20 am Sep 8 - Sep 25
3184 6:00 am 7:20 am Sep 6 - Sep 6
2250 6:05 am 7:25 am Aug 1 - Aug 8
57 6:40 am 8:00 am Aug 15 - Aug 29
2088 9:30 am 11:05 am Sep 8 - Sep 11
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
620 9:30 am 11:05 am Sep 6 - Sep 6
620 9:30 am 11:05 am Sep 7 - Sep 7
4623 10:45 am 12:20 pm Aug 15 - Aug 29
6641 10:45 am 12:20 pm Sep 5 - Sep 5
483 11:25 am 1:00 pm Sep 6 - Sep 6
483 11:25 am 1:00 pm Sep 7 - Oct 30
483 11:25 am 1:00 pm Aug 9 - Sep 4
2842 12:40 pm 2:15 pm Aug 8 - Aug 8
5657 1:45 pm 3:15 pm Sep 5 - Sep 5
748 1:45 pm 3:15 pm Aug 15 - Aug 29
2958 3:10 pm 4:40 pm Sep 6 - Sep 6
381 3:15 pm 4:45 pm Aug 9 - Sep 4
381 3:15 pm 4:45 pm Sep 7 - Sep 25
5075 4:25 pm 6:00 pm Sep 5 - Sep 5
719 4:25 pm 6:00 pm Aug 15 - Aug 29
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 Sep 8 - Sep 10
2743 5:50 pm 7:25 pm Aug 10 - Aug 28
2743 5:50 pm 7:25 pm Aug 31 - Sep 4
5028 5:50 pm 7:20 pm Sep 7 - Sep 7
5028 5:50 pm 7:20 pm Sep 6 - Sep 6
3374 6:30 pm 8:00 pm Aug 15 - Aug 29
6211 6:30 pm 8:00 pm Sep 5 - Sep 5
1576 6:55 pm 8:30 pm Aug 9 - Sep 4
2059 6:55 pm 8:30 pm Sep 6 - Sep 10
5288 6:55 pm 8:30 pm Aug 8 - Aug 8
4280 7:55 pm 9:25 pm Aug 15 - Aug 29
5223 7:55 pm 9:25 pm Sep 5 - Sep 5
402 8:55 pm 10:20 pm Aug 8 - Aug 8
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
3886 6:00 am 7:20 am Aug 15 - Aug 29
769 6:00 am 7:15 am Aug 8 - Aug 8
1571 6:15 am 7:35 am Sep 8 - Sep 25
1571 6:15 am 7:35 am Aug 10 - Sep 4
1098 6:20 am 7:40 am Sep 7 - Sep 7
5119 6:25 am 7:45 am Sep 5 - Sep 5
1591 9:35 am 10:55 am Sep 6 - Sep 6
1591 9:35 am 10:55 am Aug 9 - Aug 30
1591 9:35 am 10:55 am Sep 7 - Sep 13
1826 9:35 am 10:55 am Aug 10 - Sep 4
2212 9:50 am 11:05 am Aug 15 - Aug 29
6398 9:50 am 11:05 am Sep 5 - Sep 5
1211 12:00 pm 1:15 pm Aug 1 - Aug 8
1586 12:25 pm 1:50 pm Aug 10 - Sep 4
1586 12:25 pm 1:50 pm Sep 8 - Sep 25
1586 12:25 pm 1:50 pm Aug 9 - Aug 30
670 12:25 pm 1:50 pm Sep 6 - Sep 6
799 12:25 pm 1:50 pm Sep 7 - Sep 7
1339 3:40 pm 5:00 pm Aug 15 - Aug 29
6016 3:40 pm 5:00 pm Sep 5 - Sep 5
1582 4:30 pm 5:55 pm Aug 9 - Sep 4
3389 4:30 pm 5:55 pm Sep 6 - Sep 6
484 4:30 pm 5:55 pm Sep 7 - Sep 7
484 4:30 pm 5:55 pm Sep 8 - Sep 10
2563 5:55 pm 7:40 pm Aug 1 - Aug 8
5541 5:55 pm 7:25 pm Sep 5 - Sep 5
62 5:55 pm 7:25 pm Aug 22 - Aug 29
62 5:55 pm 7:25 pm Aug 15 - Aug 15
1833 6:25 pm 7:55 pm Sep 7 - Sep 7
2460 6:25 pm 7:55 pm Sep 8 - Oct 30
2460 6:25 pm 7:55 pm Aug 9 - Sep 4
3661 6:25 pm 7:55 pm Sep 6 - Sep 6
976 8:50 pm 10:15 pm Sep 6 - Sep 6
976 8:50 pm 10:15 pm Aug 9 - Sep 4
976 8:50 pm 10:15 pm Sep 7 - Oct 30
Airports
Origin

New York
only $154
only $184
Newark
$176
Destination

Chicago
$154