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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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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 Aug 16 2016 Return: Tue Aug 30 2016 Trip spans 15 days
Southwest
Southwest
LGA
MDW
2h 40m
nonstop
MDW
LGA
2h 00m
nonstop
Depart: Wed May 25 2016 Return: Wed Jun 1 2016 Trip spans 8 days
Delta
Delta
JFK
MDW
7h 32m
1 stop
MDW
JFK
6h 45m
1 stop
Depart: Sat Sep 24 2016 Return: Mon Sep 26 2016 Trip spans 3 days
Major Airline
Major Airline
EWR
MDW
10h 10m
1 stop
MDW
EWR
4h 59m
1 stop
Depart: Wed Sep 21 2016 Return: Thu Sep 29 2016 Trip spans 9 days
Southwest
Southwest
LGA
MDW
2h 15m
nonstop
MDW
LGA
2h 00m
nonstop
Depart: Wed Jun 15 2016 Return: Mon Jun 20 2016 Trip spans 6 days
Delta
Delta
JFK
MDW
5h 48m
1 stop
MDW
JFK
4h 25m
1 stop
Depart: Tue May 17 2016 Return: Tue May 24 2016 Trip spans 8 days
Southwest
Southwest
LGA
MDW
2h 25m
nonstop
MDW
LGA
2h 00m
nonstop
Depart: Tue Jun 21 2016 Return: Mon Jun 27 2016 Trip spans 7 days
Delta
Delta
JFK
MDW
4h 12m
1 stop
MDW
JFK
4h 25m
1 stop
Depart: Wed Jun 1 2016 Return: Tue Jun 7 2016 Trip spans 7 days
Southwest
Southwest
LGA
MDW
2h 25m
nonstop
MDW
LGA
2h 05m
nonstop
Depart: Tue Jul 12 2016 Return: Wed Jul 20 2016 Trip spans 9 days
Delta
Delta
JFK
MDW
7h 48m
1 stop
MDW
JFK
5h 25m
1 stop
Depart: Thu Jun 16 2016 Return: Tue Jun 21 2016 Trip spans 6 days
Southwest
Southwest
LGA
MDW
2h 20m
nonstop
MDW
LGA
2h 05m
nonstop
Depart: Wed Jul 13 2016 Return: Tue Jul 19 2016 Trip spans 7 days
Delta
Delta
JFK
MDW
5h 46m
1 stop
MDW
JFK
3h 45m
1 stop
Depart: Tue Jul 5 2016 Return: Fri Jul 8 2016 Trip spans 4 days
Southwest
Southwest
LGA
MDW
2h 30m
nonstop
MDW
LGA
2h 05m
nonstop
Depart: Tue Jul 19 2016 Return: Wed Jul 20 2016 Trip spans 2 days
Delta
Delta
JFK
MDW
4h 13m
1 stop
MDW
JFK
5h 25m
1 stop
Depart: Wed Jul 27 2016 Return: Tue Aug 2 2016 Trip spans 7 days
Southwest
Southwest
LGA
MDW
2h 20m
nonstop
MDW
LGA
2h 05m
nonstop
Depart: Wed Aug 24 2016 Return: Sat Aug 27 2016 Trip spans 4 days
Delta
Delta
JFK
MDW
4h 13m
1 stop
MDW
JFK
5h 22m
1 stop
Depart: Thu Aug 25 2016 Return: Sat Aug 27 2016 Trip spans 3 days
Delta
Delta
JFK
MDW
7h 48m
1 stop
MDW
JFK
5h 22m
1 stop
Depart: Sun May 8 2016 Return: Mon May 9 2016 Trip spans 2 days
Southwest
Southwest
LGA
MDW
2h 25m
nonstop
MDW
LGA
2h 05m
nonstop
Depart: Tue Sep 27 2016 Return: Sat Oct 1 2016 Trip spans 5 days
Delta
Delta
JFK
MDW
4h 12m
1 stop
MDW
JFK
3h 40m
1 stop
Depart: Tue Jun 14 2016 Return: Wed Jun 15 2016 Trip spans 2 days
Southwest
Southwest
LGA
MDW
2h 20m
nonstop
MDW
LGA
2h 05m
nonstop
Depart: Sat Oct 1 2016 Return: Tue Oct 4 2016 Trip spans 4 days
Delta
Delta
JFK
MDW
7h 03m
1 stop
MDW
JFK
7h 25m
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
6366 6:00 am 7:20 am Jun 5 - Jun 26
5737 6:05 am 7:25 am Jun 11 - Jun 25
6176 6:05 am 7:30 am May 29 - May 30
1923 6:10 am 7:30 am Jun 6 - Jul 1
2114 6:10 am 7:35 am May 31 - Jun 3
2114 6:10 am 7:35 am Apr 28 - May 27
2116 6:25 am 7:50 am Apr 30 - May 21
2116 6:25 am 7:50 am Jun 4 - Jun 4
3956 6:25 am 7:50 am May 28 - May 28
1660 8:15 am 9:30 am Jun 11 - Jun 25
2123 9:35 am 11:05 am May 31 - Jun 3
2123 9:35 am 11:05 am Apr 28 - May 27
3664 9:55 am 11:20 am May 29 - May 30
5750 9:55 am 11:30 am Jun 11 - Jul 30
1932 10:00 am 11:35 am Jun 5 - Jun 26
1932 10:00 am 11:35 am Jun 6 - Jul 1
2136 10:10 am 11:45 am Jun 4 - Jun 4
2136 10:10 am 11:45 am Apr 30 - May 28
166 11:30 am 1:00 pm Jun 4 - Jun 4
166 11:30 am 1:00 pm Apr 30 - May 21
166 11:30 am 1:00 pm May 28 - May 28
2268 11:45 am 1:20 pm Jun 11 - Jun 25
1491 11:55 am 1:25 pm May 31 - Jun 3
1491 11:55 am 1:25 pm Apr 28 - May 27
1924 11:55 am 1:35 pm Jun 5 - Jul 1
5736 11:55 am 1:25 pm May 29 - May 30
3812 12:50 pm 2:15 pm May 28 - May 28
3812 12:50 pm 2:15 pm Jun 4 - Jun 4
3812 12:50 pm 2:15 pm Apr 30 - May 21
1928 2:35 pm 3:55 pm Jun 5 - Jul 1
1746 3:15 pm 4:50 pm Jun 4 - Jun 4
1746 3:15 pm 4:50 pm Apr 30 - May 28
1155 4:00 pm 5:30 pm Apr 28 - May 27
1155 4:00 pm 5:30 pm May 31 - Jun 3
3749 4:00 pm 5:35 pm May 28 - May 28
4306 4:00 pm 5:35 pm May 29 - May 30
3749 4:10 pm 5:45 pm Apr 30 - May 21
3749 4:10 pm 5:45 pm Jun 4 - Jun 4
1937 4:35 pm 6:10 pm Jun 5 - Jul 1
5866 4:45 pm 6:15 pm Jun 11 - Jul 30
1646 5:55 pm 7:30 pm Apr 28 - May 27
1646 5:55 pm 7:30 pm May 31 - Jun 3
495 5:55 pm 7:30 pm May 29 - May 30
3542 6:20 pm 8:00 pm Jun 5 - Jul 1
2101 7:00 pm 8:25 pm May 31 - Jun 3
2101 7:00 pm 8:25 pm May 8 - May 27
2104 7:00 pm 8:30 pm May 30 - May 30
994 7:00 pm 8:30 pm May 29 - May 29
1523 8:55 pm 10:20 pm May 31 - Jun 3
1523 8:55 pm 10:20 pm Apr 28 - May 27
1931 8:55 pm 10:25 pm Jun 5 - Jul 1
5763 8:55 pm 10:20 pm May 29 - May 30
5578 9:25 pm 11:00 pm Jun 11 - Aug 6
Flight # Depart EWR Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1407 6:00 am 7:15 am Jun 6 - Jul 1
1536 6:00 am 7:15 am May 9 - May 13
1536 6:00 am 7:15 am May 16 - May 27
1536 6:00 am 7:15 am May 31 - Jun 3
1565 6:00 am 7:15 am Jun 5 - Jun 26
3806 6:00 am 7:15 am Jun 11 - Jun 25
5772 6:00 am 7:15 am May 30 - May 30
2234 6:25 am 7:40 am May 28 - May 28
3190 6:25 am 7:40 am Jun 4 - Jun 4
3190 6:25 am 7:40 am Apr 30 - May 21
1544 9:35 am 11:00 am Apr 28 - May 27
1544 9:35 am 11:00 am May 31 - Jun 3
3148 9:35 am 11:00 am May 29 - May 30
1414 9:50 am 11:10 am Jun 5 - Jul 1
1410 12:00 pm 1:15 pm Jun 5 - Jul 1
2480 12:05 pm 1:20 pm May 31 - Jun 3
2480 12:05 pm 1:20 pm Apr 28 - May 27
6426 12:05 pm 1:20 pm May 29 - May 30
845 1:30 pm 2:45 pm Jun 11 - Aug 6
749 2:05 pm 3:20 pm Apr 30 - Jun 4
3393 3:35 pm 4:55 pm May 29 - May 29
3147 3:40 pm 5:00 pm Jun 5 - Jul 1
3393 3:45 pm 5:05 pm Apr 28 - May 27
3393 3:45 pm 5:05 pm May 31 - Jun 3
4216 3:55 pm 5:15 pm May 30 - May 30
1725 5:05 pm 6:25 pm May 29 - May 30
1051 5:10 pm 6:35 pm Jun 5 - Jun 26
1051 5:10 pm 6:35 pm Jun 6 - Jul 1
2978 5:10 pm 6:30 pm May 1 - May 22
2978 5:10 pm 6:30 pm Apr 28 - May 27
2978 5:10 pm 6:30 pm May 31 - Jun 3
3986 5:25 pm 6:55 pm Apr 30 - May 21
3986 5:25 pm 6:55 pm Jun 4 - Jun 4
3986 5:25 pm 6:55 pm May 28 - May 28
5897 5:30 pm 7:05 pm Jun 11 - Jun 25
2241 6:00 pm 7:35 pm Jun 5 - Jul 1
2112 6:25 pm 7:55 pm May 31 - Jun 3
2112 6:25 pm 7:55 pm May 29 - May 29
2112 6:25 pm 7:55 pm Apr 28 - May 27
6768 6:25 pm 8:00 pm May 30 - May 30
1179 8:55 pm 10:15 pm Apr 28 - May 27
1179 8:55 pm 10:15 pm May 31 - Jun 3
345 8:55 pm 10:20 pm Jun 5 - Jul 1
5537 8:55 pm 10:15 pm May 29 - May 30
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find on occasion that certain prices are no longer available.

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Airports
Origin

New York
only $173
only $184
Newark
$193
Destination

Chicago
$173