
Keep the following information in mind while searching for Pennsylvania to Illinois flight deals. Data was last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (Justfly.com) |
One-way from | $89 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $300 |
Good round-trip deal | $299 or less |
Good one-way deal | $167 or less |
Fly from
Fly to
Route
Depart
Return
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Tue 12/8
6:24 am-8:00 am
Nonstop2h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 1/5
7:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Tue 12/8
7:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - ORD Chicago O'Hare Intl
PHLORD
Philadelphia
Thu 12/10
6:31 pm-7:20 am
1 stop13h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Wed 1/13
6:05 am-2:45 pm
2 stops9h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaMoline
PHL Philadelphia - MLI Moline Quad-City
PHLMLI
Philadelphia
Fri 1/22
6:41 pm-11:51 am
1 stop18h 10m
Moline Quad-City
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 12/11
11:40 am-12:50 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Thu 11/26
1:25 pm-2:35 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PhiladelphiaChicago
PHL Philadelphia - MDW Chicago Midway
PHLMDW
Philadelphia
Fri 1/22
1:25 pm-2:35 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
PittsburghChicago
PIT Pittsburgh - ORD Chicago O'Hare Intl
PITORD
Pittsburgh
Tue 12/29
8:45 am-9:45 am
Nonstop2h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
Everything you need to know about your flight from Pennsylvania to Illinois
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
Reza,Jun 2026
TPA - MDW
Find useful and relevant information for your journey from Pennsylvania to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$300 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$383 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$152 | Average$389 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$403 | FlexibilityNo cancel fee | On-time69% |