Find Cheap 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
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 Pittsburgh to Chicago Midway

(Round-trip)
Depart: Tue May 23 2017 Return: Sun Jun 25 2017 Trip spans 34 days
Delta
Delta
PIT
3:10a
MDW
8:29a
5h 19m
1 stop
MDW
2:50p
PIT
6:18p
3h 28m
1 stop
Depart: Wed May 24 2017 Return: Sun Jun 25 2017 Trip spans 33 days
Delta
Delta
PIT
7:24a
MDW
12:20p
4h 56m
1 stop
MDW
2:50p
PIT
6:18p
3h 28m
1 stop
Depart: Thu May 25 2017 Return: Tue May 30 2017 Trip spans 6 days
Delta
Delta
PIT
2:05a
MDW
5:46a
3h 41m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
1 stop
Depart: Tue May 9 2017 Return: Wed May 10 2017 Trip spans 2 days
Delta
Delta
PIT
8:50a
MDW
2:17p
5h 27m
1 stop
MDW
8:15a
PIT
12:20p
4h 05m
1 stop
Depart: Thu Jun 1 2017 Return: Sun Jun 4 2017 Trip spans 4 days
Delta
Delta
PIT
2:45a
MDW
7:29a
4h 44m
1 stop
MDW
2:00a
PIT
7:08a
5h 08m
1 stop
Depart: Sun May 14 2017 Return: Tue May 16 2017 Trip spans 3 days
Delta
Delta
PIT
1:50a
MDW
6:46a
4h 56m
1 stop
MDW
2:00a
PIT
7:08a
5h 08m
1 stop
Depart: Tue May 16 2017 Return: Mon May 22 2017 Trip spans 7 days
Delta
Delta
PIT
2:45a
MDW
7:29a
4h 44m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
1 stop
Depart: Wed May 17 2017 Return: Mon May 22 2017 Trip spans 6 days
Delta
Delta
PIT
9:35a
MDW
1:19p
3h 44m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
1 stop
Depart: Thu May 18 2017 Return: Mon May 22 2017 Trip spans 5 days
Delta
Delta
PIT
2:05a
MDW
5:46a
3h 41m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
1 stop
Depart: Fri May 26 2017 Return: Sun May 28 2017 Trip spans 3 days
Delta
Delta
PIT
2:05a
MDW
5:46a
3h 41m
1 stop
MDW
2:00a
PIT
7:07a
5h 07m
1 stop
Depart: Sat May 27 2017 Return: Sun May 28 2017 Trip spans 2 days
Delta
Delta
PIT
2:05a
MDW
6:18a
4h 13m
1 stop
MDW
5:16a
PIT
8:08a
2h 52m
1 stop
Depart: Sun May 28 2017 Return: Sat Jun 3 2017 Trip spans 7 days
Delta
Delta
PIT
7:24a
MDW
12:19p
4h 55m
1 stop
MDW
1:32p
PIT
6:13p
4h 41m
1 stop
Depart: Tue May 30 2017 Return: Sun Jun 4 2017 Trip spans 6 days
Delta
Delta
PIT
6:08a
MDW
9:23a
3h 15m
1 stop
MDW
2:00a
PIT
7:08a
5h 08m
1 stop
Depart: Fri Jun 2 2017 Return: Sun Jun 4 2017 Trip spans 3 days
Delta
Delta
PIT
12:37p
MDW
5:00p
4h 23m
1 stop
MDW
2:00a
PIT
7:08a
5h 08m
1 stop
Depart: Mon Jun 5 2017 Return: Wed Jun 7 2017 Trip spans 3 days
Delta
Delta
PIT
2:45a
MDW
8:38a
5h 53m
1 stop
MDW
1:00p
PIT
6:15p
5h 15m
1 stop
Depart: Tue Jun 6 2017 Return: Thu Jun 8 2017 Trip spans 3 days
Delta
Delta
PIT
1:50a
MDW
6:46a
4h 56m
1 stop
MDW
1:00p
PIT
6:15p
5h 15m
1 stop
Depart: Wed Jun 7 2017 Return: Thu Jun 8 2017 Trip spans 2 days
Delta
Delta
PIT
7:24a
MDW
12:20p
4h 56m
1 stop
MDW
3:20a
PIT
8:49a
5h 29m
1 stop
Depart: Thu Jun 8 2017 Return: Fri Jun 9 2017 Trip spans 2 days
Delta
Delta
PIT
2:05a
MDW
5:46a
3h 41m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
1 stop
Depart: Fri Jun 9 2017 Return: Sat Jun 10 2017 Trip spans 2 days
Delta
Delta
PIT
2:30p
MDW
7:20p
4h 50m
1 stop
MDW
4:45a
PIT
8:07a
3h 22m
1 stop
Depart: Mon Jun 12 2017 Return: Tue Jun 13 2017 Trip spans 2 days
Delta
Delta
PIT
2:25a
MDW
5:46a
3h 21m
1 stop
MDW
8:16a
PIT
1:49p
5h 33m
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
1306 6:00 am 6:25 am May 30 - Jun 2
1306 6:00 am 6:25 am Apr 26 - May 26
4618 7:05 am 7:35 am Apr 30 - May 7
4618 7:05 am 7:35 am May 14 - May 21
5083 7:20 am 7:50 am Apr 29 - Jun 3
152 7:40 am 8:10 am May 30 - Jun 2
152 7:40 am 8:10 am May 9 - May 26
152 7:40 am 8:10 am May 8 - May 8
3456 7:45 am 8:15 am Apr 25 - May 5
4369 8:20 am 8:45 am May 29 - May 29
1420 8:55 am 9:20 am May 28 - May 28
4868 9:55 am 10:20 am May 14 - May 21
4868 9:55 am 10:20 am Apr 30 - May 7
2115 12:45 pm 1:10 pm Apr 29 - Jun 3
4716 2:35 pm 3:00 pm May 28 - May 28
6142 2:45 pm 3:10 pm May 11 - May 11
2956 2:55 pm 3:20 pm May 14 - May 21
2956 2:55 pm 3:20 pm Apr 30 - May 7
3142 3:00 pm 3:25 pm May 12 - May 26
3142 3:00 pm 3:25 pm May 29 - May 29
3142 3:00 pm 3:25 pm May 30 - Jun 2
3142 3:00 pm 3:25 pm Apr 25 - May 10
1163 5:00 pm 5:25 pm Apr 29 - Jun 3
1602 5:05 pm 5:30 pm May 1 - May 8
1602 5:05 pm 5:30 pm May 9 - May 26
1602 5:05 pm 5:30 pm May 30 - Jun 2
1792 5:05 pm 5:30 pm May 29 - May 29
2887 5:20 pm 5:45 pm Apr 30 - May 28
1472 7:05 pm 7:30 pm May 29 - May 29
3388 7:05 pm 7:30 pm May 30 - Jun 2
3388 7:05 pm 7:30 pm Apr 25 - May 26
4677 7:05 pm 7:30 pm Apr 30 - May 7
4677 7:05 pm 7:30 pm May 28 - May 28
4677 7:05 pm 7:30 pm May 14 - May 21
* 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

Pittsburgh
$272
Destination

Chicago
$272
Airlines