Cheap Flights from Chicago to Pittsburgh
Looking for cheap flights from Chicago to Pittsburgh? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Pittsburgh vary by season, cabin, and date, but available award flights can start around 4,500–7,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Pittsburgh for specific travel dates.
2026-07-27
ORD - PIT
Economy | Non stop | 9+ left
From 4,500 Pts + $18.1
2026-07-16
ORD - PIT
Economy | 1 Stop | 9+ left
From 6,900 Pts + $5.6
2026-07-17
ORD - PIT
Economy | 1 Stop | 9+ left
From 6,900 Pts + $5.6
2026-07-14
ORD - PIT
Economy | Non stop
From 7,000 Pts + $5.6
2026-07-15
ORD - PIT
Economy | 1 Stop
From 7,000 Pts + $5.6
2026-07-12
ORD - PIT
Economy | 1 Stop
From 7,000 Pts + $11.2
Premium cabin flights from Chicago to Pittsburgh
Premium cabin
2026-06-29
ORD - PIT
First | 1 Stop | 5 left
From 15,000 Pts + $18.1
Premium cabin
2026-06-30
ORD - PIT
First | 1 Stop | 6 left
From 15,000 Pts + $18.1
Premium cabin
2026-07-01
ORD - PIT
First | 1 Stop | 1 left
From 15,000 Pts + $18.1
Premium cabin
2026-06-28
ORD - PIT
First | Non stop
From 18,000 Pts + $5.6
Premium cabin
2026-06-29
ORD - PIT
First | Non stop
From 18,000 Pts + $5.6
Premium cabin
2026-06-30
ORD - PIT
First | Non stop
From 18,000 Pts + $5.6
Selected hotels for your next stay
Pittsburgh (United States)
Hotel Indigo Pittsburgh East Liberty
From 17,000 Pts or $140
Pittsburgh (United States)
Kimpton Hotel Monaco Pittsburgh
From 32,000 Pts or $227
Pittsburgh, PA (USA)
The Industrialist Hotel, Pittsburgh, Autograph Collection
From Pts or $223
Frequently Asked Questions
The cheapest route from Chicago to Pittsburgh depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Pittsburgh.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Pittsburgh.
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