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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Book cheap flights from New York to Chicago Midway

(Round-trip)
Depart: Wed Aug 31 2016 Return: Tue Sep 20 2016 Trip spans 21 days
Depart: Mon Sep 19 2016 Return: Tue Oct 4 2016 Trip spans 16 days
Depart: Sat Aug 27 2016 Return: Tue Sep 27 2016 Trip spans 32 days
Depart: Wed Sep 7 2016 Return: Wed Sep 14 2016 Trip spans 8 days
Depart: Sat Nov 5 2016 Return: Tue Nov 8 2016 Trip spans 4 days
Depart: Mon Sep 19 2016 Return: Wed Sep 21 2016 Trip spans 3 days
Depart: Sat Sep 24 2016 Return: Fri Sep 30 2016 Trip spans 7 days
Depart: Mon Aug 29 2016 Return: Wed Sep 14 2016 Trip spans 17 days
Depart: Wed Oct 19 2016 Return: Sat Oct 22 2016 Trip spans 4 days
Depart: Tue Oct 18 2016 Return: Thu Oct 20 2016 Trip spans 3 days
Depart: Tue Aug 30 2016 Return: Wed Sep 7 2016 Trip spans 9 days
Depart: Sat Oct 22 2016 Return: Tue Oct 25 2016 Trip spans 4 days
Depart: Fri Nov 4 2016 Return: Mon Nov 7 2016 Trip spans 4 days
Depart: Wed Sep 14 2016 Return: Sat Sep 17 2016 Trip spans 4 days
Depart: Tue Oct 4 2016 Return: Sat Oct 8 2016 Trip spans 5 days
Depart: Sat Dec 3 2016 Return: Sat Dec 10 2016 Trip spans 8 days
Depart: Tue Nov 1 2016 Return: Sat Nov 5 2016 Trip spans 5 days
Depart: Thu Jan 5 2017 Return: Sat Jan 7 2017 Trip spans 3 days
Depart: Wed Nov 2 2016 Return: Sat Nov 12 2016 Trip spans 11 days
Depart: Thu Oct 13 2016 Return: Sat Oct 15 2016 Trip spans 3 days
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
5737 6:00 am 7:20 am Aug 6 - Aug 6
2070 6:05 am 7:20 am Aug 7 - Sep 30
1923 6:10 am 7:30 am Jul 26 - Aug 5
3816 6:20 am 7:30 am Sep 3 - Sep 3
3816 6:20 am 7:30 am Aug 13 - Aug 27
3240 7:45 am 9:00 am Aug 13 - Aug 27
3240 7:50 am 9:05 am Sep 3 - Sep 3
1660 8:15 am 9:30 am Jul 30 - Aug 6
3805 9:35 am 11:05 am Aug 13 - Aug 27
5750 9:55 am 11:30 am Aug 6 - Aug 6
1932 10:00 am 11:35 am Jul 26 - Aug 5
2078 10:00 am 11:30 am Aug 7 - Sep 30
4577 10:55 am 12:25 pm Sep 3 - Sep 3
2268 11:45 am 1:20 pm Aug 6 - Aug 6
1924 11:55 am 1:35 pm Jul 26 - Aug 5
2947 11:55 am 1:25 pm Aug 7 - Sep 30
3586 1:45 pm 3:10 pm Aug 13 - Oct 1
1928 2:35 pm 3:55 pm Jul 26 - Aug 5
2757 2:35 pm 4:00 pm Aug 7 - Sep 30
1937 4:35 pm 6:10 pm Jul 26 - Aug 5
2080 4:45 pm 6:15 pm Aug 7 - Sep 30
5866 4:45 pm 6:15 pm Aug 6 - Aug 6
3542 6:20 pm 8:00 pm Jul 26 - Aug 5
1797 6:30 pm 8:05 pm Sep 3 - Sep 3
1797 6:35 pm 8:15 pm Aug 13 - Aug 27
2117 7:00 pm 8:35 pm Sep 4 - Sep 4
249 7:15 pm 8:55 pm Aug 7 - Sep 2
2686 8:00 pm 9:30 pm Aug 13 - Aug 27
185 8:55 pm 10:20 pm Aug 7 - Nov 4
1931 8:55 pm 10:25 pm Jul 26 - Aug 5
5578 9:25 pm 11:00 pm Jul 30 - Aug 6
Flight # Depart EWR Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1407 6:00 am 7:15 am Aug 6 - Aug 6
1407 6:00 am 7:15 am Jul 26 - Aug 5
1540 6:15 am 7:25 am Aug 8 - Sep 2
349 6:15 am 7:25 am Sep 4 - Sep 4
4034 6:15 am 7:25 am Aug 7 - Aug 28
3441 6:20 am 7:30 am Aug 13 - Oct 1
1414 9:50 am 11:10 am Jul 26 - Aug 5
1551 9:50 am 11:00 am Aug 7 - Sep 30
1410 12:00 pm 1:15 pm Jul 26 - Aug 5
2597 12:00 pm 1:10 pm Sep 4 - Sep 5
4052 12:00 pm 1:10 pm Aug 7 - Sep 2
3714 12:35 pm 1:45 pm Sep 3 - Sep 3
565 12:35 pm 1:45 pm Aug 13 - Aug 27
845 1:30 pm 2:45 pm Jul 30 - Aug 6
1553 3:35 pm 4:55 pm Sep 4 - Oct 1
1553 3:35 pm 4:55 pm Sep 3 - Sep 3
1553 3:35 pm 4:55 pm Aug 7 - Sep 2
3147 3:40 pm 5:00 pm Jul 26 - Aug 5
482 5:05 pm 6:25 pm Aug 8 - Sep 2
1051 5:10 pm 6:35 pm Jul 26 - Aug 5
3569 5:10 pm 6:30 pm Sep 4 - Sep 4
4101 5:10 pm 6:30 pm Aug 7 - Aug 28
2072 5:15 pm 6:40 pm Aug 13 - Oct 1
5897 5:35 pm 7:10 pm Aug 6 - Aug 6
1544 6:00 pm 7:30 pm Aug 7 - Sep 2
2241 6:00 pm 7:35 pm Jul 26 - Aug 5
1544 6:05 pm 7:35 pm Sep 4 - Sep 5
1597 8:50 pm 10:05 pm Aug 7 - Sep 2
1597 8:55 pm 10:10 pm Sep 4 - Sep 5
345 8:55 pm 10:20 pm Jul 26 - Aug 5
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

We compile tonnes 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 can'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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

New York
only $94
only $172
Newark
$162
Destination

Chicago
$94