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 Oct 4 2016 Return: Tue Oct 25 2016 Trip spans 22 days
Depart: Fri Dec 9 2016 Return: Tue Dec 13 2016 Trip spans 5 days
Depart: Tue Sep 13 2016 Return: Wed Sep 21 2016 Trip spans 9 days
Depart: Sat Sep 10 2016 Return: Tue Sep 13 2016 Trip spans 4 days
Depart: Wed Oct 26 2016 Return: Mon Oct 31 2016 Trip spans 6 days
Depart: Wed Jan 4 2017 Return: Wed Jan 18 2017 Trip spans 15 days
Depart: Thu Sep 8 2016 Return: Tue Sep 13 2016 Trip spans 6 days
Depart: Wed Sep 14 2016 Return: Thu Sep 15 2016 Trip spans 2 days
Depart: Tue Sep 20 2016 Return: Wed Sep 21 2016 Trip spans 2 days
Depart: Tue Sep 20 2016 Return: Tue Sep 27 2016 Trip spans 8 days
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
Depart: Fri Nov 11 2016 Return: Sun Nov 13 2016 Trip spans 3 days
Depart: Wed Sep 21 2016 Return: Tue Sep 27 2016 Trip spans 7 days
Depart: Fri Sep 9 2016 Return: Mon Sep 12 2016 Trip spans 4 days
Depart: Wed Sep 28 2016 Return: Tue Oct 11 2016 Trip spans 14 days
Depart: Thu Aug 25 2016 Return: Tue Sep 13 2016 Trip spans 20 days
Depart: Fri Sep 30 2016 Return: Mon Oct 3 2016 Trip spans 4 days
Depart: Tue Oct 4 2016 Return: Sat Oct 8 2016 Trip spans 5 days
Depart: Sat Oct 1 2016 Return: Mon Oct 3 2016 Trip spans 3 days
Depart: Tue Feb 14 2017 Return: Mon Feb 27 2017 Trip spans 14 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
2070 6:05 am 7:20 am Aug 21 - Sep 30
3816 6:20 am 7:30 am Sep 3 - Sep 3
3816 6:20 am 7:30 am Sep 10 - Oct 1
3240 7:45 am 9:00 am Sep 10 - Oct 1
3240 7:50 am 9:05 am Sep 3 - Sep 3
3805 9:35 am 11:05 am Sep 10 - Oct 1
2078 10:00 am 11:30 am Aug 21 - Sep 30
4577 10:55 am 12:25 pm Sep 3 - Sep 3
2947 11:55 am 1:25 pm Aug 21 - Sep 30
3586 1:45 pm 3:10 pm Aug 20 - Oct 1
2757 2:35 pm 4:00 pm Aug 21 - Sep 30
2080 4:45 pm 6:15 pm Aug 21 - Sep 30
1797 6:30 pm 8:05 pm Sep 3 - Sep 3
1797 6:35 pm 8:15 pm Sep 10 - Oct 1
2117 7:00 pm 8:35 pm Sep 4 - Sep 4
249 7:10 pm 8:50 pm Sep 5 - Sep 5
249 7:15 pm 8:55 pm Aug 21 - Sep 2
249 7:15 pm 8:55 pm Sep 6 - Sep 30
2686 8:00 pm 9:30 pm Sep 10 - Nov 5
185 8:55 pm 10:20 pm Aug 21 - Nov 4
Flight # Depart EWR Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1540 6:15 am 7:25 am Aug 22 - Sep 2
1540 6:15 am 7:25 am Sep 6 - Sep 30
349 6:15 am 7:25 am Sep 4 - Sep 4
4034 6:15 am 7:25 am Sep 11 - Sep 25
3441 6:20 am 7:30 am Aug 20 - Oct 1
4844 6:25 am 7:35 am Sep 5 - Sep 5
1551 9:50 am 11:00 am Aug 21 - Sep 30
2597 12:00 pm 1:10 pm Sep 4 - Sep 5
4052 12:00 pm 1:10 pm Aug 21 - Sep 2
4052 12:00 pm 1:10 pm Sep 6 - Sep 30
3714 12:35 pm 1:45 pm Sep 3 - Sep 3
565 12:35 pm 1:45 pm Sep 10 - Oct 1
1553 3:35 pm 4:55 pm Sep 3 - Sep 3
1553 3:35 pm 4:55 pm Sep 4 - Oct 1
1553 3:35 pm 4:55 pm Aug 20 - Sep 2
482 5:05 pm 6:25 pm Sep 6 - Sep 30
482 5:05 pm 6:25 pm Aug 22 - Sep 2
3569 5:10 pm 6:30 pm Sep 4 - Sep 4
4101 5:10 pm 6:30 pm Sep 11 - Sep 25
482 5:10 pm 6:30 pm Sep 5 - Sep 5
2072 5:15 pm 6:40 pm Aug 20 - Oct 1
1544 6:00 pm 7:30 pm Sep 6 - Sep 30
1544 6:00 pm 7:30 pm Aug 21 - Sep 2
1544 6:05 pm 7:35 pm Sep 4 - Sep 5
1597 8:50 pm 10:05 pm Sep 6 - Sep 30
1597 8:50 pm 10:05 pm Aug 21 - Sep 2
1597 8:55 pm 10:10 pm Sep 4 - Sep 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 $89
only $164
Newark
$173
Destination

Chicago
$89