Cheap Flights from Chicago to Pittsburgh
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 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.
2026-11-05
ORD - PIT
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-06
ORD - PIT
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-07
ORD - PIT
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-09
ORD - PIT
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-10
ORD - PIT
Economy | Non stop | 8 left
From 4,500 Pts + $25.6
2026-11-11
ORD - PIT
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
Chicago to Pittsburgh flight facts
Distance
414 mi
665 km in a straight line
Estimated flight time
about 1h 15m
In the air, for the straight-line distance
Time difference
+1h
Pittsburgh is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Pittsburgh
PIT · Pittsburgh Intl
Nearby airport alternatives
Flights Chicago - Morgantown · Morgantown is 61 mi from Pittsburgh
Flights Chicago - Akron · Akron is 70 mi from Pittsburgh
Flights Chicago - Cleveland · Cleveland is 106 mi from Pittsburgh
Flights Madison - Pittsburgh · Madison is 111 mi from Chicago
Flights Chicago - State College Pennsylvania · State College Pennsylvania is 127 mi from Pittsburgh
Flights Chicago - Columbus · Columbus is 144 mi from Pittsburgh
Premium cabin flights from Chicago to Pittsburgh
Premium cabin
2026-11-13
ORD - PIT
First | Non stop | 2 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-14
ORD - PIT
First | Non stop | 6 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - PIT
First | Non stop | 2 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - PIT
First | Non stop | 4 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-18
ORD - PIT
First | Non stop | 3 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-19
ORD - PIT
First | Non stop | 2 left
From 9,000 Pts + $25.6
Selected hotels for your next stay
Pittsburgh, PA (USA)
The Industrialist Hotel, Pittsburgh, Autograph Collection
From Pts or $166
Pittsburgh, PA (USA)
The Oaklander Hotel, Autograph Collection
From Pts or $185
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.
Chicago and Pittsburgh are about 414 miles (665 km) apart in a straight line.
Flying the 414-mile straight-line distance takes about 1h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Pittsburgh is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Pittsburgh: Pittsburgh Intl (PIT).
Travelers searching this route also look at other popular routes into Pittsburgh, plus the return trip when we track it. Fares and award space change daily.
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points travel planning experience. Yeah!
