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.
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: Thu Sep 22 2016 Return: Sat Sep 24 2016 Trip spans 3 days
Depart: Wed Sep 7 2016 Return: Wed Sep 14 2016 Trip spans 8 days
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
Depart: Sat Sep 10 2016 Return: Wed Sep 14 2016 Trip spans 5 days
Depart: Fri Aug 26 2016 Return: Mon Sep 26 2016 Trip spans 32 days
Depart: Sat Oct 1 2016 Return: Tue Oct 4 2016 Trip spans 4 days
Depart: Wed Aug 17 2016 Return: Sat Aug 20 2016 Trip spans 4 days
Depart: Sat Nov 5 2016 Return: Sat Nov 12 2016 Trip spans 8 days
Depart: Sat Oct 8 2016 Return: Thu Oct 13 2016 Trip spans 6 days
Depart: Thu Nov 17 2016 Return: Mon Nov 21 2016 Trip spans 5 days
Depart: Thu Aug 18 2016 Return: Mon Aug 22 2016 Trip spans 5 days
Depart: Sun Jun 12 2016 Return: Tue Jun 14 2016 Trip spans 3 days
Depart: Tue Sep 13 2016 Return: Tue Sep 20 2016 Trip spans 8 days
Depart: Fri Nov 4 2016 Return: Wed Nov 9 2016 Trip spans 6 days
Depart: Thu Oct 20 2016 Return: Wed Oct 26 2016 Trip spans 7 days
Depart: Fri Jul 15 2016 Return: Wed Aug 17 2016 Trip spans 34 days
Depart: Sat Sep 3 2016 Return: Sat Sep 10 2016 Trip spans 8 days
Depart: Thu Sep 8 2016 Return: Mon Sep 12 2016 Trip spans 5 days
Depart: Mon Jul 18 2016 Return: Wed Jul 20 2016 Trip spans 3 days
Depart: Sun Jun 19 2016 Return: Tue Jun 21 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
3277 6:00 am 7:20 am Jul 3 - Jul 3
5737 6:00 am 7:20 am Jul 2 - Jul 2
6366 6:00 am 7:20 am Jun 5 - Jun 26
6543 6:00 am 7:20 am Jul 4 - Jul 4
5737 6:05 am 7:25 am Jun 11 - Jun 25
1923 6:10 am 7:30 am Jul 5 - Aug 5
1923 6:10 am 7:30 am Jun 6 - Jul 1
2116 6:25 am 7:50 am Jun 4 - Jun 4
1660 8:15 am 9:30 am Jul 2 - Jul 2
1660 8:15 am 9:30 am Jun 11 - Jun 25
5750 9:55 am 11:30 am Jul 3 - Jul 3
5750 9:55 am 11:30 am Jun 11 - Jul 30
1932 10:00 am 11:35 am Jun 6 - Jul 1
1932 10:00 am 11:35 am Jul 5 - Aug 5
1932 10:00 am 11:35 am Jun 5 - Jun 26
4577 10:00 am 11:35 am Jul 4 - Jul 4
2136 10:10 am 11:45 am Jun 4 - Jun 4
166 11:30 am 1:00 pm Jun 4 - Jun 4
2268 11:45 am 1:20 pm Jun 11 - Jun 25
6401 11:45 am 1:20 pm Jul 2 - Jul 2
1924 11:55 am 1:35 pm Jun 5 - Jul 1
1924 11:55 am 1:35 pm Jul 5 - Aug 5
2749 11:55 am 1:35 pm Jul 4 - Jul 4
2749 11:55 am 1:35 pm Jul 3 - Jul 3
3812 12:50 pm 2:15 pm Jun 4 - Jun 4
1928 2:35 pm 3:55 pm Jul 5 - Aug 5
1928 2:35 pm 3:55 pm Jun 5 - Jul 1
6146 2:35 pm 3:55 pm Jul 3 - Jul 4
1746 3:15 pm 4:50 pm Jun 4 - Jun 4
3749 4:10 pm 5:45 pm Jun 4 - Jun 4
1425 4:35 pm 6:10 pm Jul 3 - Jul 4
1937 4:35 pm 6:10 pm Jun 5 - Jul 1
1937 4:35 pm 6:10 pm Jul 5 - Aug 5
5866 4:45 pm 6:15 pm Jun 11 - Jul 30
3542 6:20 pm 8:00 pm Jun 5 - Jul 1
3542 6:20 pm 8:00 pm Jul 5 - Aug 5
710 6:20 pm 8:00 pm Jul 3 - Jul 3
710 6:20 pm 8:00 pm Jul 4 - Jul 4
1931 8:55 pm 10:25 pm Jun 5 - Jul 1
1931 8:55 pm 10:25 pm Jul 5 - Aug 5
2754 8:55 pm 10:25 pm Jul 3 - Jul 4
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
1407 6:00 am 7:15 am Jul 2 - Jul 8
1565 6:00 am 7:15 am Jun 5 - Jun 26
3806 6:00 am 7:15 am Jun 11 - Jun 25
6721 6:00 am 7:15 am Jul 4 - Jul 4
2655 6:05 am 7:20 am Jul 3 - Jul 3
3190 6:25 am 7:40 am Jun 4 - Jun 4
1414 9:50 am 11:10 am Jul 5 - Aug 5
1414 9:50 am 11:10 am Jun 5 - Jul 1
2473 9:50 am 11:10 am Jul 3 - Jul 3
6129 9:50 am 11:10 am Jul 4 - Jul 4
1410 12:00 pm 1:15 pm Jul 5 - Aug 5
1410 12:00 pm 1:15 pm Jun 5 - Jul 1
2464 12:00 pm 1:15 pm Jul 3 - Jul 4
845 1:30 pm 2:45 pm Jun 11 - Aug 6
749 2:05 pm 3:20 pm May 28 - Jun 4
3147 3:40 pm 5:00 pm Jul 5 - Aug 5
3147 3:40 pm 5:00 pm Jun 5 - Jul 1
1068 3:45 pm 5:05 pm Jul 3 - Jul 4
1051 5:10 pm 6:35 pm Jun 5 - Jun 26
1051 5:10 pm 6:35 pm Jun 6 - Jul 1
1051 5:10 pm 6:35 pm Jul 5 - Aug 5
3521 5:10 pm 6:35 pm Jul 4 - Jul 4
3521 5:10 pm 6:35 pm Jul 3 - Jul 3
3986 5:25 pm 6:55 pm Jun 4 - Jun 4
5897 5:30 pm 7:05 pm Jun 11 - Jun 25
5897 5:35 pm 7:10 pm Jul 2 - Jul 2
2241 6:00 pm 7:35 pm Jun 5 - Jul 1
2241 6:00 pm 7:35 pm Jul 5 - Aug 5
2465 6:00 pm 7:35 pm Jul 3 - Jul 4
1578 8:55 pm 10:20 pm Jul 3 - Jul 4
345 8:55 pm 10:20 pm Jul 5 - Aug 5
345 8:55 pm 10:20 pm Jun 5 - Jul 1
* 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.

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 $171
only $190
Newark
$188
Destination

Chicago
$171