
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Super.com) |
One-way from | $96 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $304 |
Good round-trip deal | $308 or less |
Good one-way deal | $160 or less |
Fly from
Fly to
Route
Depart
Return
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Tue 8/25
1:55 pm-9:00 pm
1 stop8h 05m
Chicago Midway
Fri 8/28
9:30 am-12:25 pm
Nonstop1h 55m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Tue 7/28
6:25 am-12:34 pm
1 stop7h 09m
Chicago O'Hare Intl
Tue 8/4
8:02 am-2:53 pm
1 stop5h 51m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Sat 8/15
6:05 am-9:17 am
1 stop4h 12m
Chicago Midway
Sat 8/15
4:39 pm-1:19 am
1 stop7h 40m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Sat 7/18
6:10 am-9:08 am
1 stop3h 58m
Chicago Midway
Tue 7/21
6:00 am-1:24 pm
1 stop6h 24m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Tue 8/4
7:15 am-3:25 pm
2 stops9h 10m
Chicago Midway
Tue 8/11
4:40 pm-9:50 pm
1 stop4h 10m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 7/8
7:25 am-8:30 am
Nonstop2h 05m
Chicago Midway
Thu 7/9
6:55 pm-9:55 pm
Nonstop2h 00m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 8/5
3:00 pm-4:00 pm
Nonstop2h 00m
Chicago Midway
Sun 8/9
8:20 pm-11:15 pm
Nonstop1h 55m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 8/12
6:25 am-11:50 am
1 stop6h 25m
Chicago Midway
Sun 8/16
9:45 am-12:40 pm
Nonstop1h 55m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Sat 6/27
8:20 am-9:30 am
Nonstop2h 10m
Chicago Midway
Tue 6/30
7:45 am-10:50 am
Nonstop2h 05m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Wed 8/26
3:58 pm-8:50 pm
1 stop5h 52m
Chicago O'Hare Intl
Sun 8/30
6:40 am-2:47 pm
1 stop7h 07m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
Currently, February is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $40). Flying from Philadelphia to Chicago in January is currently the most expensive (average of $938). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s optimal to fly from Philadelphia to Chicago in the evening. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight at noon.
The most flights from PHL to CHI are scheduled on a Sunday (55 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).
About 18% of weekly flights between Philadelphia and Chicago have experienced delays in the past year, with the average delay time being 145 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
The price you pay for your flight from Philadelphia to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 55 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Walter,May 2026
LAS - BUR
Comfort
Overall
Boarding
Entertainment
Food
Crew
Reviews
Walter,May 2026
LAS - BUR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$173 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$337 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$332 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$161 | Average$321 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$161 | Average$339 | FlexibilityNo cancel fee | On-time69% |