For a quick trip to ORD, take the 'L' train from downtown Chicago, avoiding traffic delays common with taxis or rideshares.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $173 (Southwest) |
One-way from | $51 (Super.com) |
Popular in | December |
Cheapest in | August |
Average price | $218 |
Good round-trip deal | $237 or less |
Good one-way deal | $134 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Sat 2/28
7:45 am-5:45 pm
2 stops9h 00m
Pittsburgh
Mon 3/2
6:55 pm-7:30 pm
Nonstop1h 35m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Tue 2/10
1:25 pm-3:45 pm
Nonstop1h 20m
Pittsburgh
Tue 2/17
6:00 am-12:30 pm
2 stops7h 30m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Thu 2/12
6:00 am-12:36 pm
1 stop5h 36m
Pittsburgh
Wed 2/18
10:28 am-12:46 pm
1 stop3h 18m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Wed 2/25
6:20 pm-10:37 pm
1 stop3h 17m
Pittsburgh
Wed 3/4
6:30 am-1:05 pm
1 stop7h 35m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Tue 3/17
5:40 pm-10:40 pm
1 stop4h 00m
Pittsburgh
Wed 3/18
10:55 am-4:00 pm
1 stop6h 05m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Thu 4/9
9:30 am-4:26 pm
1 stop5h 56m
Pittsburgh
Tue 4/14
10:29 am-12:30 pm
1 stop3h 01m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Thu 4/9
9:35 am-1:27 pm
1 stop2h 52m
Pittsburgh
Mon 4/13
10:08 am-4:36 pm
1 stop7h 28m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Mon 2/9
1:45 pm-9:20 pm
1 stop6h 35m
Pittsburgh
Thu 2/12
6:00 am-12:15 pm
1 stop7h 15m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Sat 4/11
5:40 pm-10:46 pm
1 stop4h 06m
Pittsburgh
Mon 4/13
12:25 pm-6:04 pm
1 stop6h 39m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Wed 2/11
12:15 pm-8:11 pm
1 stop6h 56m
Pittsburgh
Wed 2/18
6:00 am-10:45 am
1 stop5h 45m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Pittsburgh is 85 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, December is the cheapest month in which you can book a flight from Chicago to Pittsburgh (average of $90). Flying from Chicago to Pittsburgh in July is currently the most expensive (average of $194). 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.
A simple way to save on the total cost of your ticket is to fly from Chicago to Pittsburgh in the evening. If you’re flexible enough to do this you can expect to save up to 11% on your trip compared to booking a flight in the afternoon.
Travelers seeking maximum savings on their Chicago to Pittsburgh flight should consider departing on Tuesday mornings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to PIT are scheduled on a Friday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (32 on average).
About 14% of weekly flights between Chicago and Pittsburgh have experienced delays in the past year, with the average delay time being 106 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 14% of flights being delayed.
Food
Comfort
Entertainment
Boarding
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Comfort
Entertainment
Boarding
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Comfort
Entertainment
Boarding
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Comfort
Entertainment
Boarding
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$290 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$103 | Average$291 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$312 | FlexibilityNo cancel fee | On-time69% |