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 | $117 (Southwest)  | 
One-way from | $49 (Southwest)  | 
Popular in | June | 
Cheapest in | August | 
Average price | $325 | 
Good round-trip deal | $156 or less | 
Good one-way deal | $48 or less | 
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Wed 1/28
10:15 am-12:40 pm
Nonstop1h 25m
Pittsburgh
Wed 2/4
12:15 pm-12:45 pm
Nonstop1h 30m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Wed 1/28
1:45 pm-8:45 pm
1 stop6h 00m
Pittsburgh
Wed 2/4
6:25 am-12:15 pm
1 stop6h 50m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Thu 12/4
6:30 pm-9:00 pm
Nonstop1h 30m
Pittsburgh
Mon 12/8
8:15 am-9:12 am
Nonstop1h 57m
ChicagoPittsburgh
MDW - PIT
MDWPIT
Chicago Midway
Sat 1/17
5:00 pm-11:46 pm
1 stop5h 46m
Pittsburgh
Sun 1/18
6:00 am-10:34 am
1 stop5h 34m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Sat 1/17
8:00 am-3:43 pm
1 stop6h 43m
Pittsburgh
Sun 1/18
10:24 am-1:07 pm
1 stop3h 43m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Tue 12/2
1:59 pm-4:35 pm
Nonstop1h 36m
Pittsburgh
Wed 12/3
8:15 am-9:12 am
Nonstop1h 57m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Mon 11/17
7:34 pm-9:11 pm
2 stops24h 37m
Pittsburgh
Mon 12/1
10:42 pm-9:01 am
1 stop11h 19m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Sat 1/24
5:05 am-7:36 pm
1 stop13h 31m
Pittsburgh
Sat 1/31
8:31 pm-9:23 am
1 stop13h 52m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Wed 11/19
6:45 am-4:42 pm
1 stop8h 57m
Pittsburgh
Mon 11/24
4:39 pm-10:50 pm
1 stop7h 11m
ChicagoPittsburgh
ORD - PIT
ORDPIT
Chicago O'Hare Intl
Wed 1/28
5:05 am-10:37 pm
1 stop16h 32m
Pittsburgh
Wed 2/4
2:18 pm-11:42 pm
2 stops10h 24m
| 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, October is the cheapest month in which you can book a flight from Chicago to Pittsburgh (average of $97). 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 morning. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Chicago to Pittsburgh flight should consider departing on Tuesday mornings when fares are most often at their lowest. Monday 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 Sunday (46 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Overall
Food
Boarding
Crew
Comfort
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$103 | Average$296 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$300 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$116 | Average$335 | FlexibilityNo cancel fee | On-time69% |