S$236 Cheap Flights from Philadelphia to Chicago

View S$236 flight on Fri, 6 Mar, 2026Opens in a new window

Popular airlines from Philadelphia Intl. Airport (PHL) to Chicago

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Cheap Flights from Philadelphia to Chicago (PHL-CHI)

Prices were available within the past 7 days and start at S$236 for one-way flights and S$525 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$525 Return, found 5 days ago
S$525
Return
found 5 days ago
Select United flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$525 found 5 days ago
United
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$526 Return, found 5 days ago
S$526
Return
found 5 days ago
Select United flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$526 found 5 days ago
Delta
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$527 Return, found 5 days ago
S$527
Return
found 5 days ago
Select Delta flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$527 found 5 days ago
American Airlines
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$538 Return, found 5 days ago
S$538
Return
found 5 days ago
Select American Airlines flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$538 found 5 days ago
United
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$539 Return, found 5 days ago
S$539
Return
found 5 days ago
Select United flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$539 found 5 days ago
Delta
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$540 Return, found 5 days ago
S$540
Return
found 5 days ago
Select Delta flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$540 found 5 days ago
American Airlines
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$551 Return, found 5 days ago
S$551
Return
found 5 days ago
Select American Airlines flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$551 found 5 days ago
American Airlines
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$552 Return, found 5 days ago
S$552
Return
found 5 days ago
Select American Airlines flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$552 found 5 days ago
Delta
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$553 Return, found 5 days ago
S$553
Return
found 5 days ago
Select Delta flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$553 found 5 days ago
American Airlines
Fri, 26 Dec - Mon, 29 Dec
PHL
Philadelphia
ORD
Chicago
S$564 Return, found 5 days ago
S$564
Return
found 5 days ago
Select American Airlines flight, departing Fri, 26 Dec from Philadelphia to Chicago, returning Mon, 29 Dec, priced at S$564 found 5 days ago

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Find the cheapest month to fly from Philadelphia (PHL) to Chicago (CHI)

October is typically the cheapest month to fly

From S$102 - S$205 per traveller.
Philadelphia to Chicago route information
Origin airport
Philadelphia Intl.
Destination airport
O'Hare Intl.
Return price
S$525
Distance
1081 km

Perfect flights from Philadelphia to Chicago

Your Journey from Philadelphia to Chicago

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*Note: Prices may vary based on availability and are subject to change.

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Chicago Airports

Chicago

Philadelphia to O'Hare Intl.
S$524.90
*Available to Expedia members.