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: Mon Jan 30 2017 Return: Tue Jan 31 2017 Trip spans 2 days
Delta
Delta
PIT
5:11a
MDW
8:34a
3h 23m
1 stop
MDW
1:45a
PIT
5:16a
3h 31m
1 stop
Depart: Tue Jan 31 2017 Return: Thu Feb 2 2017 Trip spans 3 days
Delta
Delta
PIT
8:39a
MDW
12:11p
3h 32m
1 stop
MDW
1:45a
PIT
5:16a
3h 31m
1 stop
Depart: Wed Feb 1 2017 Return: Fri Feb 3 2017 Trip spans 3 days
Delta
Delta
PIT
4:45a
MDW
9:33a
4h 48m
1 stop
MDW
1:45a
PIT
5:16a
3h 31m
1 stop
Depart: Thu Feb 2 2017 Return: Fri Feb 3 2017 Trip spans 2 days
Delta
Delta
PIT
1:10a
MDW
4:40a
3h 30m
1 stop
MDW
1:45a
PIT
5:16a
3h 31m
1 stop
Depart: Fri Feb 3 2017 Return: Sat Feb 4 2017 Trip spans 2 days
Delta
Delta
PIT
4:45a
MDW
9:33a
4h 48m
1 stop
MDW
3:45a
PIT
7:17a
3h 32m
1 stop
Depart: Sat Feb 4 2017 Return: Mon Feb 6 2017 Trip spans 3 days
Delta
Delta
PIT
1:10a
MDW
5:08a
3h 58m
1 stop
MDW
7:35a
PIT
12:44p
5h 09m
1 stop
Depart: Mon Feb 6 2017 Return: Wed Feb 8 2017 Trip spans 3 days
Delta
Delta
PIT
1:10a
MDW
4:40a
3h 30m
1 stop
MDW
4:15a
PIT
9:36a
5h 21m
1 stop
Depart: Tue Feb 7 2017 Return: Thu Feb 9 2017 Trip spans 3 days
Delta
Delta
PIT
8:39a
MDW
12:11p
3h 32m
1 stop
MDW
1:42a
PIT
5:16a
3h 34m
1 stop
Depart: Wed Feb 8 2017 Return: Thu Feb 9 2017 Trip spans 2 days
Delta
Delta
PIT
12:45p
MDW
6:46p
6h 01m
1 stop
MDW
1:42a
PIT
5:16a
3h 34m
1 stop
Depart: Thu Feb 9 2017 Return: Fri Feb 10 2017 Trip spans 2 days
Delta
Delta
PIT
1:10a
MDW
4:40a
3h 30m
1 stop
MDW
1:40p
PIT
5:20p
3h 40m
1 stop
Depart: Fri Feb 10 2017 Return: Sun Feb 12 2017 Trip spans 3 days
Delta
Delta
PIT
5:11a
MDW
8:34a
3h 23m
1 stop
MDW
5:58a
PIT
11:08a
5h 10m
1 stop
Depart: Sat Feb 11 2017 Return: Mon Feb 13 2017 Trip spans 3 days
Delta
Delta
PIT
8:40a
MDW
1:19p
4h 39m
1 stop
MDW
10:40a
PIT
3:48p
5h 08m
1 stop
Depart: Mon Feb 13 2017 Return: Wed Feb 15 2017 Trip spans 3 days
Delta
Delta
PIT
12:40p
MDW
5:00p
4h 20m
1 stop
MDW
1:42a
PIT
5:16a
3h 34m
1 stop
Depart: Tue Feb 21 2017 Return: Thu Feb 23 2017 Trip spans 3 days
Delta
Delta
PIT
8:37a
MDW
12:06p
3h 29m
1 stop
MDW
4:14a
PIT
9:37a
5h 23m
1 stop
Depart: Wed Feb 22 2017 Return: Thu Feb 23 2017 Trip spans 2 days
Delta
Delta
PIT
1:05a
MDW
4:39a
3h 34m
1 stop
MDW
1:50a
PIT
5:15a
3h 25m
1 stop
Depart: Thu Feb 23 2017 Return: Mon Feb 27 2017 Trip spans 5 days
Delta
Delta
PIT
1:05a
MDW
4:39a
3h 34m
1 stop
MDW
1:40p
PIT
5:23p
3h 43m
1 stop
Depart: Fri Feb 24 2017 Return: Sun Feb 26 2017 Trip spans 3 days
Delta
Delta
PIT
1:05a
MDW
4:39a
3h 34m
1 stop
MDW
1:40p
PIT
5:23p
3h 43m
1 stop
Depart: Sat Feb 25 2017 Return: Sat Mar 4 2017 Trip spans 8 days
Delta
Delta
PIT
1:05a
MDW
5:30a
4h 25m
1 stop
MDW
2:10a
PIT
6:30a
4h 20m
1 stop
Depart: Sun Feb 26 2017 Return: Sat Mar 4 2017 Trip spans 7 days
Delta
Delta
PIT
6:50a
MDW
11:23a
4h 33m
1 stop
MDW
2:10a
PIT
6:30a
4h 20m
1 stop
Depart: Mon Feb 27 2017 Return: Sat Mar 4 2017 Trip spans 6 days
Delta
Delta
PIT
8:15a
MDW
1:50p
5h 35m
1 stop
MDW
4:00a
PIT
7:25a
3h 25m
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
216 6:40 am 7:20 am Jan 17 - Feb 13
216 6:40 am 7:20 am Feb 15 - Mar 8
6783 6:45 am 7:25 am Feb 14 - Feb 14
2507 7:05 am 7:50 am Jan 21 - Mar 4
3544 7:10 am 7:55 am Feb 12 - Mar 5
3544 7:10 am 7:55 am Jan 22 - Jan 29
6291 7:10 am 7:55 am Feb 5 - Feb 5
6769 8:35 am 9:10 am Feb 14 - Feb 14
3231 8:55 am 9:30 am Jan 17 - Feb 13
3231 8:55 am 9:30 am Feb 15 - Mar 8
2800 1:25 pm 1:55 pm Feb 12 - Mar 5
2800 1:25 pm 1:55 pm Jan 22 - Jan 29
5867 1:25 pm 1:55 pm Feb 5 - Feb 5
1397 4:10 pm 4:40 pm Jan 17 - Feb 13
1397 4:10 pm 4:40 pm Feb 15 - Mar 8
6548 4:15 pm 4:45 pm Feb 14 - Feb 14
5411 5:05 pm 5:35 pm Feb 4 - Mar 4
1302 5:50 pm 6:30 pm Feb 13 - Feb 17
1302 5:50 pm 6:30 pm Feb 20 - Mar 8
1302 5:50 pm 6:30 pm Feb 14 - Feb 14
1302 5:50 pm 6:30 pm Jan 30 - Jan 31
1302 5:50 pm 6:30 pm Jan 17 - Jan 27
1302 5:50 pm 6:30 pm Feb 1 - Feb 10
1967 6:05 pm 6:40 pm Feb 5 - Feb 5
5632 6:05 pm 6:40 pm Jan 22 - Jan 29
5632 6:05 pm 6:40 pm Feb 12 - Mar 5
606 9:40 pm 10:15 pm Feb 7 - Feb 13
606 9:40 pm 10:15 pm Feb 16 - Mar 8
606 9:40 pm 10:15 pm Jan 17 - Feb 3
* 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.

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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.

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Airports
Origin

Pittsburgh
$280
Destination

Chicago
$280
Airlines