Southwest offers two free checked bags, even for oversized items like skis.
Southwest's open seating policy allows passengers to choose any available seat.
Round-trip from | $154 (Southwest) |
---|---|
One-way from | $96 (Delta) |
Popular in | January |
Cheapest in | August |
Average price | $295 |
Good round-trip deal | $266 or less |
Good one-way deal | $162 or less |
Fly from
Fly to
Route
Depart
Return
Price
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Thu 9/25
5:00 pm-10:00 pm
1 stop6h 00m
Chicago Midway
Sun 9/28
8:00 am-2:30 pm
1 stop5h 30m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Mon 8/4
4:09 pm-5:05 pm
Nonstop1h 56m
Chicago O'Hare Intl
Sat 8/16
9:10 pm-11:48 pm
Nonstop1h 38m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Wed 8/27
6:00 am-11:50 am
1 stop6h 50m
Chicago O'Hare Intl
Sat 8/30
2:55 pm-7:55 pm
1 stop4h 00m
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Fri 7/11
3:49 pm-11:51 pm
1 stop9h 02m
Chicago Midway
Mon 7/14
8:35 am-7:38 pm
1 stop10h 03m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 8/15
8:38 pm-9:24 pm
Nonstop1h 46m
Chicago O'Hare Intl
Sun 8/24
8:54 pm-11:44 pm
Nonstop1h 50m
PittsburghChicago
PIT - MDW
PITMDW
Pittsburgh
Wed 8/13
5:56 pm-9:44 pm
1 stop4h 48m
Chicago Midway
Tue 8/19
6:04 am-12:38 pm
1 stop5h 34m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Mon 8/4
6:31 pm-12:09 am
1 stop6h 38m
Chicago O'Hare Intl
Tue 8/12
5:45 am-12:38 pm
1 stop5h 53m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Thu 7/31
3:14 pm-10:15 pm
1 stop8h 01m
Chicago O'Hare Intl
Mon 8/4
5:40 am-4:45 pm
1 stop10h 05m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Mon 9/8
6:45 am-5:39 pm
1 stop11h 54m
Chicago O'Hare Intl
Wed 9/10
11:45 am-11:22 pm
1 stop10h 37m
PittsburghChicago
PIT - ORD
PITORD
Pittsburgh
Fri 9/5
9:36 am-7:40 pm
1 stop11h 04m
Chicago O'Hare Intl
Sat 9/6
11:45 am-11:22 pm
1 stop10h 37m
The price you pay for your flight from Pittsburgh to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, August is the cheapest month in which you can book a flight from Pittsburgh to Chicago (average of $245). Flying from Pittsburgh to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike at noon, when flights are generally more expensive, you can save up to 36% on flights from Pittsburgh to Chicago by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Pittsburgh to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from PIT to CHI are scheduled on a Tuesday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
John,May 2025
PVD - BNA
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
John,May 2025
PVD - BNA
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
John,May 2025
PVD - BNA
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
John,May 2025
PVD - BNA
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
John,May 2025
PVD - BNA
Comfort
Crew
Food
Boarding
Entertainment
Overall
Reviews
John,May 2025
PVD - BNA
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$119 | Average$304 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$126 | Average$319 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$138 | Average$321 | FlexibilityNo cancel fee | On-time69% |