Cheap flights from Pittsburgh to Chicago from $115 PIT → ORD
Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD)
The cheapest return found recently is $422 with American Airlines, 27 Dec – 3 Jan 2027, found 3 days ago. The cheapest one-way found recently is $115 with American Airlines, 21 Nov, found 2 days ago.
- Cheapest one-way found recently
- $115, American Airlines, found 2 days ago
- Cheapest return found recently
- $422, 27 Dec to 3 Jan 2027
- Cheapest month to fly
- November 2026, one-way fares from $115 found in the last 7 days
- Airlines with nonstop flights
- American Airlines
- Shortest nonstop flight found
- 2 h 6 min
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$422
27 Dec – 3 Jan 2027 · American Airlines
Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD)
Leaves 6:00 a.m. · Return leaves 1:00 p.m. · 6 h 48 min of travel, both ways together
out 1 stop, back nonstop
found 3 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$422 27 Dec – 3 Jan 2027found 3 days agoSee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 35 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $236 to $550.
Those were the prices on those days, not today's.
Is this a good return price?
Not enough comparable prices yet: we hold return fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 7-night return fares leaving within 3 days of 27 Dec to compare.
Every date we hold
1 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 27 Dec – 3 Jan 2027 | $422 | American Airlines | Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 3 days ago | See prices for these dates |
Airlines on the cheapest dates: American Airlines.
One-way
The cheapest one-way fare on each of 5 departure dates is usually $148 to $150.
Cheapest one-way found recently
$115
21 Nov · American Airlines
Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD)
Leaves 8:29 p.m. · 2 h 6 min trip
nonstop
found 2 days ago
Cheapest nonstop one-way
$115
21 Nov · American Airlines
Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD)
Leaves 8:29 p.m. · 2 h 6 min trip
nonstop
found 2 days ago
Found recently, and the cheapest we hold
$115 21 Novfound 2 days agoOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 30 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $94 to $204.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 5 departure dates from 17 Nov to 5 Mar 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 21 Nov to compare.
Every date we hold
5 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 17 Nov | $148 | Frontier Airlines | Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD) | 1 stop | found 6 days ago | Open this trip |
| 21 Nov | $115 | American Airlines | Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD) | nonstop | found 2 days ago | Open this trip |
| 27 Dec | $226 | American Airlines | Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD) | 1 stop | found 3 days ago | Open this trip |
| 25 Feb 2027 | $150 | jetBlue | Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD) | 1 stop | found 2 days ago | Open this trip |
| 5 Mar 2027 | $150 | jetBlue | Pittsburgh International Airport (PIT) → O'Hare International Airport (ORD) | 1 stop | found 2 days ago | Open this trip |
Which month looks cheapest?
November 2026 is the cheapest month — from $115.
Airlines on the cheapest dates: American Airlines, jetBlue, Frontier Airlines.
Premium cabin fares from Pittsburgh to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 27 Dec – 3 Jan 2027 in another cabin: Premium economy · Business · First
Today's prices for 21 Nov in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Pittsburgh to Chicago?
Return
The cheapest fares were 14 to 29 days before departure.
From the cheapest return each day between 24 Sept and 11 Nov (35 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 14–29 days | $267 | $236 | Cheapest seen | 11 |
| 30–59 days | $355 | $273 | +33% | 29 |
| 60–89 days | $269 | $269 | +1% | 8 |
One-way
The cheapest fares were 7 to 13 days before departure.
From the cheapest one-way each day between 24 Sept and 11 Nov (30 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 7–13 days | $124 | $100 | Cheapest seen | 12 |
| 14–29 days | $130 | $130 | +5% | 11 |
| 30–59 days | $147 | $147 | +19% | 9 |
| 90–179 days | $204 | $150 | +65% | 9 |
Live price for these dates
The cheapest return found recently is for 27 Dec – 3 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Pittsburgh to Chicago?
The cheapest return found recently is $422 with American Airlines, 27 Dec to 3 Jan 2027, found 3 days ago.
How much is a one-way flight from Pittsburgh to Chicago?
The cheapest one-way found recently is $115 with American Airlines, 21 Nov, found 2 days ago. The cheapest one-way fare on each of 5 departure dates is usually $148 to $150.
What is the cheapest month to fly from Pittsburgh to Chicago?
November 2026 is the cheapest month for a one-way, from $115, 21 Nov, found 2 days ago.
How far ahead should I book a flight from Pittsburgh to Chicago?
In 35 days of prices between 24 Sept and 11 Nov, return fares were cheapest 14 to 29 days before departure. In 30 days of prices between 24 Sept and 11 Nov, one-way fares were cheapest 7 to 13 days before departure.
Is there a direct flight from Pittsburgh to Chicago?
Yes, the cheapest nonstop one-way found recently is $115 with American Airlines, 21 Nov, found 2 days ago.
How long is the flight from Pittsburgh to Chicago?
The cheapest nonstop one-way found recently, with American Airlines on 21 Nov, takes 2 h 6 min from Pittsburgh International Airport (PIT) to O'Hare International Airport (ORD).
Which airlines have the cheapest flights from Pittsburgh to Chicago?
Between 17 Nov and 5 Mar 2027, American Airlines has the cheapest one-way on 2 of the 5 departure dates we hold, jetBlue on 2 and Frontier Airlines on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work