Travelers have found it’s best to book a flight 43 days in advance to save up to 22% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 43 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Pennsylvania to Chicago 1-2 weeks in advance for as low as $190, or $281 for flights within the next 24 hours.
Flights from Pennsylvania to Chicago lean towards being more expensive in June. Prices are generally better when you fly from Pennsylvania to Chicago in September, with the cheapest ticket starting at $60.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pennsylvania to Chicago as you normally would.
Fly from
Fly to
Budget
$66 - $156
Route
Depart
Return
Price
PhiladelphiaChicago Midway
PHL - MDW
PHLMDW
Philadelphia
Wed 5/1
Nonstop2h 17m
Chicago Midway
Tue 5/14
Nonstop1h 56m
PhiladelphiaChicago O'Hare Intl
PHL - ORD
PHLORD
Philadelphia
Tue 5/21
Nonstop2h 22m
Chicago O'Hare Intl
Wed 5/29
Nonstop2h 03m
PhiladelphiaChicago Midway
PHL - MDW
PHLMDW
Philadelphia
Thu 5/2
Nonstop2h 17m
Chicago Midway
Sat 5/4
Nonstop2h 01m
PhiladelphiaChicago Midway
PHL - MDW
PHLMDW
Philadelphia
Sat 4/27
Nonstop2h 17m
Chicago Midway
Mon 4/29
Nonstop2h 03m
PhiladelphiaChicago O'Hare Intl
PHL - ORD
PHLORD
Philadelphia
Wed 4/24
1 stop11h 36m
Chicago O'Hare Intl
Mon 4/29
1 stop13h 35m
PhiladelphiaChicago Midway
PHL - MDW
PHLMDW
Philadelphia
Tue 4/9
Nonstop2h 26m
Chicago Midway
Thu 4/11
1 stop12h 47m
PhiladelphiaChicago O'Hare Intl
PHL - ORD
PHLORD
Philadelphia
Wed 5/1
Nonstop2h 25m
Chicago O'Hare Intl
Wed 5/15
Nonstop2h 03m
PittsburghChicago O'Hare Intl
PIT - ORD
PITORD
Pittsburgh
Sat 5/11
Nonstop1h 38m
Chicago O'Hare Intl
Sat 5/11
Nonstop1h 29m
PittsburghChicago Midway
PIT - MDW
PITMDW
Pittsburgh
Sat 4/27
1 stop3h 45m
Chicago Midway
Sat 4/27
1 stop4h 11m
No data available for this route at this time. Please check back soon.
Entertainment
Food
Comfort
Overall
Boarding
Crew
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Food
Comfort
Overall
Boarding
Crew
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Food
Comfort
Overall
Boarding
Crew
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Food
Comfort
Overall
Boarding
Crew
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Food
Comfort
Overall
Boarding
Crew
Reviews
No tray tables for food or drink not convenient nor comfortable
Entertainment
Food
Comfort
Overall
Boarding
Crew
Reviews
No tray tables for food or drink not convenient nor comfortable
20%of flight departures | Early morningMidnight to 6 am |
---|---|
38%of flight departures | Morning6 am to noon |
41%of flight departures | AfternoonNoon to 6 pm |
1%of flight departures | Evening6 pm to midnight |
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