Find Deals on Flights from Pittsburgh to Chicago Midway (PIT - MDW)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Pittsburgh to Chicago Midway

(Round-trip)
Depart: Sun Dec 25 2016 Return: Thu Jan 5 2017 Trip spans 12 days
Delta
Delta
PIT
1:40a
MDW
6:52a
5h 12m
1 stop
MDW
2:00a
PIT
5:15a
3h 15m
1 stop
Depart: Thu Dec 15 2016 Return: Sat Dec 17 2016 Trip spans 3 days
Delta
Delta
PIT
2:50a
MDW
7:43a
4h 53m
1 stop
MDW
2:00a
PIT
5:15a
3h 15m
1 stop
Depart: Fri Dec 16 2016 Return: Sat Dec 17 2016 Trip spans 2 days
Delta
Delta
PIT
2:50a
MDW
7:43a
4h 53m
1 stop
MDW
2:00a
PIT
5:15a
3h 15m
1 stop
Depart: Sat Dec 17 2016 Return: Sun Dec 18 2016 Trip spans 2 days
Delta
Delta
PIT
1:15a
MDW
4:53a
3h 38m
1 stop
MDW
2:00a
PIT
5:15a
3h 15m
1 stop
Depart: Thu Jan 5 2017 Return: Sun Jan 8 2017 Trip spans 4 days
Delta
Delta
PIT
2:15a
MDW
7:45a
5h 30m
1 stop
MDW
12:59p
PIT
6:02p
5h 03m
1 stop
Depart: Fri Jan 6 2017 Return: Sun Jan 8 2017 Trip spans 3 days
Delta
Delta
PIT
12:15p
MDW
6:05p
5h 50m
1 stop
MDW
5:58a
PIT
11:08a
5h 10m
1 stop
Depart: Wed Jan 11 2017 Return: Thu Jan 12 2017 Trip spans 2 days
Delta
Delta
PIT
12:40p
MDW
5:00p
4h 20m
1 stop
MDW
1:45a
PIT
5:16a
3h 31m
1 stop
Depart: Thu Jan 12 2017 Return: Sat Jan 14 2017 Trip spans 3 days
Delta
Delta
PIT
6:14a
MDW
11:03a
4h 49m
1 stop
MDW
11:50a
PIT
3:35p
3h 45m
1 stop
Depart: Sun Jan 15 2017 Return: Mon Jan 16 2017 Trip spans 2 days
Delta
Delta
PIT
2:40a
MDW
9:31a
6h 51m
1 stop
MDW
1:40p
PIT
5:20p
3h 40m
1 stop
Depart: Tue Jan 17 2017 Return: Tue Jan 24 2017 Trip spans 8 days
Delta
Delta
PIT
12:40p
MDW
5:00p
4h 20m
1 stop
MDW
1:45a
PIT
5:16a
3h 31m
1 stop
Depart: Thu Jan 19 2017 Return: Sat Jan 21 2017 Trip spans 3 days
Delta
Delta
PIT
1:10a
MDW
4:40a
3h 30m
1 stop
MDW
11:50a
PIT
3:35p
3h 45m
1 stop
Depart: Fri Jan 20 2017 Return: Sun Jan 22 2017 Trip spans 3 days
Delta
Delta
PIT
2:40a
MDW
7:45a
5h 05m
1 stop
MDW
3:45a
PIT
9:36a
5h 51m
1 stop
Depart: Fri Feb 3 2017 Return: Mon Feb 6 2017 Trip spans 4 days
Delta
Delta
PIT
2:40a
MDW
7:45a
5h 05m
1 stop
MDW
9:08a
PIT
1:43p
4h 35m
1 stop
Depart: Sat Feb 11 2017 Return: Mon Feb 13 2017 Trip spans 3 days
Delta
Delta
PIT
8:39a
MDW
12:09p
3h 30m
1 stop
MDW
1:40p
PIT
5:20p
3h 40m
1 stop
Depart: Tue Feb 21 2017 Return: Fri Feb 24 2017 Trip spans 4 days
Delta
Delta
PIT
1:30a
MDW
5:01a
3h 31m
1 stop
MDW
1:35p
PIT
5:16p
3h 41m
1 stop
Depart: Fri Feb 24 2017 Return: Sun Feb 26 2017 Trip spans 3 days
Delta
Delta
PIT
8:30a
MDW
2:02p
5h 32m
1 stop
MDW
1:35p
PIT
5:16p
3h 41m
1 stop
Depart: Fri Mar 3 2017 Return: Mon Mar 6 2017 Trip spans 4 days
Delta
Delta
PIT
1:45a
MDW
8:06a
6h 21m
1 stop
MDW
1:00a
PIT
6:47a
5h 47m
1 stop
Depart: Sat Dec 24 2016 Return: Thu Jan 5 2017 Trip spans 13 days
Delta
Delta
PIT
1:15a
MDW
4:49a
3h 34m
1 stop
MDW
2:00a
PIT
5:15a
3h 15m
1 stop
Depart: Mon Mar 13 2017 Return: Wed Mar 15 2017 Trip spans 3 days
Delta
Delta
PIT
2:30a
MDW
5:48a
3h 18m
1 stop
MDW
3:00a
PIT
6:05a
3h 05m
1 stop
Depart: Thu Mar 23 2017 Return: Sun Mar 26 2017 Trip spans 4 days
Delta
Delta
PIT
2:30a
MDW
5:48a
3h 18m
1 stop
MDW
2:35p
PIT
5:58p
3h 23m
1 stop
Select an airline:  Southwest
Direct flights PIT to MDW on Southwest
Flight # Depart PIT Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
1910 6:00 am 6:30 am Dec 24 - Dec 24
428 6:00 am 6:30 am Dec 12 - Dec 20
428 6:00 am 6:30 am Jan 3 - Jan 4
428 6:00 am 6:30 am Dec 5 - Dec 9
428 6:00 am 6:30 am Dec 31 - Dec 31
5987 6:05 am 6:35 am Dec 21 - Jan 2
1434 6:20 am 6:55 am Dec 17 - Dec 17
137 6:40 am 7:20 am Jan 5 - Jan 5
216 6:40 am 7:20 am Jan 6 - Feb 13
430 7:00 am 7:50 am Dec 12 - Dec 20
430 7:00 am 7:50 am Dec 5 - Dec 9
430 7:00 am 7:50 am Jan 3 - Jan 4
2507 7:05 am 7:50 am Jan 7 - Mar 4
3544 7:10 am 7:55 am Jan 8 - Jan 29
5986 7:15 am 8:00 am Dec 21 - Jan 2
6852 8:40 am 9:10 am Dec 17 - Dec 17
3811 8:45 am 9:25 am Dec 4 - Dec 18
3811 8:45 am 9:25 am Jan 1 - Jan 1
1136 9:25 am 10:00 am Jan 5 - Jan 13
5910 9:25 am 10:00 am Dec 21 - Jan 2
1311 9:40 am 10:15 am Dec 25 - Dec 25
4168 10:55 am 11:25 am Dec 21 - Jan 2
1777 11:45 am 12:20 pm Dec 3 - Dec 10
1777 11:45 am 12:20 pm Dec 24 - Dec 24
2031 11:45 am 12:20 pm Dec 31 - Dec 31
2800 1:25 pm 1:55 pm Jan 8 - Jan 29
1071 1:45 pm 2:15 pm Dec 4 - Dec 18
1071 1:45 pm 2:15 pm Jan 1 - Jan 1
2642 1:45 pm 2:15 pm Dec 25 - Dec 25
3455 1:45 pm 2:15 pm Jan 3 - Jan 4
3455 1:45 pm 2:15 pm Dec 1 - Dec 20
5222 1:50 pm 2:20 pm Dec 17 - Dec 17
5430 2:50 pm 3:20 pm Dec 3 - Dec 10
6641 2:50 pm 3:20 pm Dec 31 - Dec 31
1847 2:55 pm 3:25 pm Dec 24 - Dec 24
4126 3:25 pm 3:55 pm Dec 21 - Jan 2
1397 4:10 pm 4:40 pm Jan 5 - Jan 5
1397 4:10 pm 4:40 pm Jan 6 - Feb 13
2643 4:45 pm 5:15 pm Dec 25 - Dec 25
441 4:45 pm 5:15 pm Dec 24 - Dec 24
2437 5:00 pm 5:30 pm Dec 31 - Dec 31
5411 5:05 pm 5:35 pm Jan 7 - Jan 21
3648 5:10 pm 5:40 pm Dec 3 - Dec 10
1409 5:20 pm 5:50 pm Dec 17 - Dec 17
279 5:35 pm 6:05 pm Jan 1 - Jan 4
279 5:35 pm 6:05 pm Dec 1 - Dec 20
1302 5:50 pm 6:30 pm Jan 6 - Jan 27
1302 5:50 pm 6:30 pm Jan 5 - Jan 5
3944 6:00 pm 6:30 pm Dec 25 - Dec 25
5632 6:05 pm 6:40 pm Jan 8 - Jan 29
1601 6:35 pm 7:05 pm Dec 21 - Jan 2
606 9:40 pm 10:15 pm Jan 5 - Feb 3
588 9:55 pm 10:20 pm Jan 1 - Jan 3
588 9:55 pm 10:20 pm Dec 1 - Dec 20
4675 10:45 pm 11:10 pm Dec 21 - Jan 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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,
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Airports
Origin

Pittsburgh
$234
Destination

Chicago
$234
Airlines