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
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: Wed Apr 19 2017 Return: Tue Apr 25 2017 Trip spans 7 days
Delta
Delta
PIT
1:16a
MDW
5:47a
4h 31m
1 stop
MDW
2:45a
PIT
6:19a
3h 34m
1 stop
Depart: Thu May 11 2017 Return: Thu May 18 2017 Trip spans 8 days
Southwest
Southwest
PIT
2:00a
MDW
3:25a
1h 25m
nonstop
MDW
6:35p
PIT
7:55p
1h 20m
nonstop
Depart: Sat Apr 22 2017 Return: Wed Apr 26 2017 Trip spans 5 days
Delta
Delta
PIT
2:30a
MDW
5:47a
3h 17m
1 stop
MDW
2:45a
PIT
6:19a
3h 34m
1 stop
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
PIT
2:30a
MDW
5:47a
3h 17m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
1 stop
Depart: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
Delta
Delta
PIT
2:30p
MDW
7:20p
4h 50m
1 stop
MDW
2:30a
PIT
7:53a
5h 23m
1 stop
Depart: Wed May 10 2017 Return: Sat May 13 2017 Trip spans 4 days
Delta
Delta
PIT
2:45a
MDW
7:29a
4h 44m
1 stop
MDW
1:52p
PIT
7:13p
5h 21m
1 stop
Depart: Sat May 13 2017 Return: Tue May 16 2017 Trip spans 4 days
Delta
Delta
PIT
2:05a
MDW
6:18a
4h 13m
1 stop
MDW
2:55a
PIT
6:10a
3h 15m
1 stop
Depart: Tue May 16 2017 Return: Sat May 20 2017 Trip spans 5 days
Delta
Delta
PIT
2:30p
MDW
7:20p
4h 50m
1 stop
MDW
1:52p
PIT
7:13p
5h 21m
1 stop
Depart: Sat May 20 2017 Return: Wed May 24 2017 Trip spans 5 days
Delta
Delta
PIT
2:05a
MDW
6:18a
4h 13m
1 stop
MDW
5:16a
PIT
10:23a
5h 07m
1 stop
Depart: Tue May 23 2017 Return: Wed May 24 2017 Trip spans 2 days
Delta
Delta
PIT
2:05a
MDW
5:46a
3h 41m
1 stop
MDW
5:16a
PIT
10:23a
5h 07m
1 stop
Depart: Wed May 24 2017 Return: Tue May 30 2017 Trip spans 7 days
Delta
Delta
PIT
6:08a
MDW
9:23a
3h 15m
1 stop
MDW
1:00p
PIT
6:15p
5h 15m
1 stop
Depart: Thu Apr 13 2017 Return: Sat Apr 15 2017 Trip spans 3 days
Delta
Delta
PIT
1:16a
MDW
5:47a
4h 31m
1 stop
MDW
5:00a
PIT
8:44a
3h 44m
1 stop
Depart: Tue Apr 18 2017 Return: Thu Apr 20 2017 Trip spans 3 days
Delta
Delta
PIT
1:16a
MDW
5:47a
4h 31m
1 stop
MDW
8:24a
PIT
12:40p
4h 16m
1 stop
Depart: Thu Apr 20 2017 Return: Sat Apr 22 2017 Trip spans 3 days
Delta
Delta
PIT
2:30a
MDW
8:47a
6h 17m
1 stop
MDW
11:52a
PIT
7:07p
7h 15m
1 stop
Depart: Mon May 1 2017 Return: Tue May 9 2017 Trip spans 9 days
Delta
Delta
PIT
3:20a
MDW
8:29a
5h 09m
1 stop
MDW
11:55a
PIT
4:35p
4h 40m
1 stop
Depart: Mon Jun 5 2017 Return: Sat Jun 10 2017 Trip spans 6 days
Delta
Delta
PIT
2:30p
MDW
7:20p
4h 50m
1 stop
MDW
1:32p
PIT
6:13p
4h 41m
1 stop
Depart: Sat Apr 15 2017 Return: Sun Apr 16 2017 Trip spans 2 days
Delta
Delta
PIT
2:30a
MDW
5:47a
3h 17m
1 stop
MDW
7:05a
PIT
11:25a
4h 20m
1 stop
Depart: Sun Apr 23 2017 Return: Tue Apr 25 2017 Trip spans 3 days
Delta
Delta
PIT
2:30a
MDW
8:47a
6h 17m
1 stop
MDW
11:52a
PIT
4:35p
4h 43m
1 stop
Depart: Wed Apr 26 2017 Return: Sun Apr 30 2017 Trip spans 5 days
Delta
Delta
PIT
2:30a
MDW
7:30a
5h 00m
1 stop
MDW
2:45p
PIT
6:10p
3h 25m
1 stop
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
Delta
Delta
PIT
6:08a
MDW
9:23a
3h 15m
1 stop
MDW
2:40p
PIT
6:15p
3h 35m
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
495 5:45 am 6:10 am Apr 25 - Apr 25
1306 6:00 am 6:25 am Apr 26 - May 26
765 6:30 am 7:05 am Mar 25 - Apr 22
1483 6:35 am 7:10 am Mar 22 - Apr 24
3134 7:05 am 7:45 am Mar 26 - Apr 23
4618 7:05 am 7:35 am Apr 30 - May 7
5083 7:20 am 7:50 am Apr 29 - Jun 3
3456 7:45 am 8:15 am Apr 25 - May 5
1211 8:10 am 8:40 am Mar 22 - Apr 24
6362 8:50 am 9:20 am Mar 25 - Apr 22
282 9:15 am 9:40 am Mar 26 - Apr 23
4868 9:55 am 10:20 am Apr 30 - May 7
984 10:45 am 11:10 am Mar 22 - Apr 24
3182 11:15 am 11:40 am Mar 26 - Apr 23
2115 12:45 pm 1:10 pm Apr 29 - Jun 3
2549 1:40 pm 2:05 pm Mar 26 - Apr 23
2956 2:55 pm 3:20 pm Apr 30 - May 7
3142 3:00 pm 3:25 pm Apr 25 - May 10
3961 4:00 pm 4:25 pm Mar 22 - Apr 24
1163 5:00 pm 5:25 pm Apr 29 - Jun 3
1602 5:05 pm 5:30 pm Apr 26 - Apr 28
1602 5:05 pm 5:30 pm May 1 - May 8
315 5:05 pm 5:30 pm Apr 25 - Apr 25
6166 5:05 pm 5:35 pm Mar 25 - Apr 22
2887 5:20 pm 5:45 pm Apr 30 - May 28
937 5:45 pm 6:10 pm Mar 22 - Apr 24
4610 6:50 pm 7:15 pm Mar 26 - Apr 23
3388 7:05 pm 7:30 pm Apr 25 - May 26
4677 7:05 pm 7:30 pm Apr 30 - May 7
* 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
$260
Destination

Chicago
$260
Airlines Airline reviews

3 travelers who booked a flight from Pittsburgh to Chicago rated their chosen airlines with an average of 9.8.

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
10.0
Food
10.0
Entertainment
8.7