Cheap Flights from Chicago to Philadelphia
Cheap Flights from Chicago to Philadelphia
Cheap Flights from Chicago to Philadelphia
Looking for cheap flights from Chicago to Philadelphia? 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 Philadelphia vary by season and date, but economy flights can start around 4,500–17,400 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 Philadelphia for specific travel dates.
2026-05-21
ORD - PHL
Economy | Non stop | 9+ left
From 12,500 Pts + $10.1
VA
2026-05-21
ORD - PHL
Economy | Non stop | 9+ left
From 4,500 Pts + $18.1
AS
2026-05-22
ORD - PHL
Economy | Non stop | 9+ left
From 4,500 Pts + $18.1
AS
2026-05-22
ORD - PHL
Economy | Non stop | 9+ left
From 12,500 Pts + $10.1
VA
2026-05-22
ORD - PHL
Economy | 1 Stop | 9+ left
From 17,400 Pts + $5.6
DL
2026-05-23
ORD - PHL
Economy | Non stop
From 16,000 Pts + $5.6
AA
Premium cabin flights from Chicago to Philadelphia
Premium cabin
2026-05-21
ORD - PHL
First | Non stop | 1 left
From 9,000 Pts + $18.1
AS
Premium cabin
2026-05-22
ORD - PHL
First | Non stop | 9+ left
From 9,000 Pts + $18.1
AS
Premium cabin
2026-05-22
ORD - PHL
First | 1 Stop | 2 left
From 35,600 Pts + $5.6
DL
Premium cabin
2026-05-23
ORD - PHL
First | Non stop | 9+ left
From 9,000 Pts + $18.1
AS
Premium cabin
2026-05-23
ORD - PHL
First | 1 Stop | 4 left
From 35,300 Pts + $5.6
DL
Premium cabin
2026-05-23
ORD - PHL
First | Non stop
From 32,500 Pts + $5.6
AA
Selected hotels for your next stay
Seaview Hotel
Galloway (United States)
Seaview Hotel
From 12,000 Pts or $262
Kimpton Hotel Palomar Philadelphia
Philadelphia (United States)
Kimpton Hotel Palomar Philadelphia
From 29,000 Pts or $247
Hotel Indigo West Chester - Downtown
West Chester (United States)
Hotel Indigo West Chester - Downtown
From 29,000 Pts or $200
Frequently Asked Questions
The cheapest route from Chicago to Philadelphia 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 Philadelphia.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Philadelphia.
Our mission is to provide
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Our mission is to provide the simplest and best
points travel planning experience. Yeah!