Cheap flights from Philadelphia to Historic Route 66

View AU$122 flight on Sat, 23 Aug. 2025Opens in a new window

Popular airlines from Philadelphia to Historic Route 66

  • Delta

    Delta

  • American Airlines

    American Airlines

  • United

    United

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Cheap Flights from Philadelphia (ILG) to Historic Route 66 (CHI)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, 4 Sep. - Thu, 25 Sep.
PHL
Philadelphia
ORD
Chicago
AU$242 Return, found 4 days ago
AU$242
Return
found 4 days ago
Select American Airlines flight, departing Thu, 4 Sep. from Philadelphia to Chicago, returning Thu, 25 Sep., priced at AU$242 found 4 days ago
American Airlines
Thu, 11 Sep. - Mon, 15 Sep.
PHL
Philadelphia
ORD
Chicago
AU$244 Return, found 5 days ago
AU$244
Return
found 5 days ago
Select American Airlines flight, departing Thu, 11 Sep. from Philadelphia to Chicago, returning Mon, 15 Sep., priced at AU$244 found 5 days ago
American Airlines
Thu, 4 Sep. - Thu, 25 Sep.
PHL
Philadelphia
ORD
Chicago
AU$296 Return, found 4 days ago
AU$296
Return
found 4 days ago
Select American Airlines flight, departing Thu, 4 Sep. from Philadelphia to Chicago, returning Thu, 25 Sep., priced at AU$296 found 4 days ago
American Airlines
Thu, 11 Sep. - Mon, 15 Sep.
PHL
Philadelphia
ORD
Chicago
AU$297 Return, found 5 days ago
AU$297
Return
found 5 days ago
Select American Airlines flight, departing Thu, 11 Sep. from Philadelphia to Chicago, returning Mon, 15 Sep., priced at AU$297 found 5 days ago
Delta
Thu, 4 Sep. - Thu, 25 Sep.
PHL
Philadelphia
ORD
Chicago
AU$302 Return, found 4 days ago
AU$302
Return
found 4 days ago
Select Delta flight, departing Thu, 4 Sep. from Philadelphia to Chicago, returning Thu, 25 Sep., priced at AU$302 found 4 days ago
United
Thu, 4 Sep. - Thu, 25 Sep.
PHL
Philadelphia
ORD
Chicago
AU$327 Return, found 4 days ago
AU$327
Return
found 4 days ago
Select United flight, departing Thu, 4 Sep. from Philadelphia to Chicago, returning Thu, 25 Sep., priced at AU$327 found 4 days ago

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

September is typically the cheapest month to fly

From AU$74 - AU$200 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.