S$99 Cheap Flights from Pittsburgh to Chicago

View S$99 flight on Mon, 24 Nov, 2025Opens in a new window

Popular airlines from Pittsburgh Intl. Airport (PIT) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Pittsburgh to Chicago (PIT-ORD)

Prices were available within the past 7 days and start at S$99 for one-way flights and S$362 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$362 Return, found 9 hours ago
S$362
Return
found 9 hours ago
Select United flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$362 found 9 hours ago
Delta
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$379 Return, found 9 hours ago
S$379
Return
found 9 hours ago
Select Delta flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$379 found 9 hours ago
United
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$382 Return, found 9 hours ago
S$382
Return
found 9 hours ago
Select United flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$382 found 9 hours ago
United
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$401 Return, found 9 hours ago
S$401
Return
found 9 hours ago
Select United flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$401 found 9 hours ago
Delta
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$418 Return, found 9 hours ago
S$418
Return
found 9 hours ago
Select Delta flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$418 found 9 hours ago
United
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$421 Return, found 9 hours ago
S$421
Return
found 9 hours ago
Select United flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$421 found 9 hours ago
American Airlines
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$433 Return, found 9 hours ago
S$433
Return
found 9 hours ago
Select American Airlines flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$433 found 9 hours ago
United
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$434 Return, found 9 hours ago
S$434
Return
found 9 hours ago
Select United flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$434 found 9 hours ago
United
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$459 Return, found 9 hours ago
S$459
Return
found 9 hours ago
Select United flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$459 found 9 hours ago
Delta
Mon, 24 Nov - Sun, 30 Nov
PIT
Pittsburgh
ORD
Chicago
S$469 Return, found 9 hours ago
S$469
Return
found 9 hours ago
Select Delta flight, departing Mon, 24 Nov from Pittsburgh to Chicago, returning Sun, 30 Nov, priced at S$469 found 9 hours ago

Find the cheapest month to fly from Pittsburgh (PIT) to Chicago (ORD)

September is typically the cheapest month to fly

From S$99 - S$179 per traveller.

Frequently asked questions

How much is a flight from PIT to O'Hare Airport?
The lowest price advertised for a round-trip flight between Pittsburgh Airport and ORD is S$362. But you better act quick. This price is taken from fares listed within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from PIT to ORD?
Every air carrier has different terms and conditions. If you decide to cancel your holiday, head to our Customer Service Portal.
How do I find cheap flights from Pittsburgh Airport to ORD that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for PIT to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from PIT to O'Hare Airport?
The flight distance from Pittsburgh Intl. Airport (PIT) (PIT) to O'Hare Intl. Airport (ORD) (ORD) is just 660 kilometres. You'll be walking down the air bridge and collecting your bags from the carousel in the blink of an eye.
Which airlines fly direct from Pittsburgh Airport to O'Hare Intl. Airport (ORD)?
United Airlines (UA) is the preferred choice for many travellers. It operates 117 flights from Pittsburgh Intl. Airport (PIT) to O'Hare Intl. Airport (ORD) each month. For more options, have a look at the ticket prices from American Airlines (AA). This carrier offers 69 monthly flights between these airports.
Are Pittsburgh Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Pittsburgh Intl. Airport (PIT) to O'Hare Intl. Airport (ORD) at the last minute could be your ticket to an awesome deal. However, it could end up costing a great deal more! If you'd rather not take any chances, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back regularly as deals are updated all the time on Expedia.

Travel information

Travel information

0
Origin airport
Pittsburgh Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
S$362
Distance
656 km

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Perfect flights from Pittsburgh to Chicago

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Pittsburgh to Chicago

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