Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.
Frontier offers Zone 1 boarding with a carry-on purchase or special fare bundle.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $106 (Kiwi.com) |
One-way from | $69 (Priceline) |
Popular in | March |
Cheapest in | September |
Average price | $198 |
Good round-trip deal | $149 or less |
Good one-way deal | $142 or less |
Fly from
Fly to
Route
Depart
Return
Price
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Wed 12/3
1:15 pm-2:35 pm
Nonstop2h 20m
Chicago O'Hare Intl
Wed 12/10
11:05 am-2:07 pm
Nonstop2h 02m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 2/18
5:45 pm-7:00 pm
Nonstop2h 15m
Chicago Midway
Wed 2/25
5:30 pm-8:20 pm
Nonstop1h 50m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Wed 12/24
5:00 pm-6:31 pm
Nonstop2h 31m
Chicago O'Hare Intl
Sat 1/10
11:20 am-2:31 pm
Nonstop2h 11m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Tue 12/2
4:00 pm-5:10 pm
Nonstop2h 10m
Chicago Midway
Tue 12/9
6:05 pm-9:00 pm
Nonstop1h 55m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Sun 1/11
6:30 am-7:59 am
Nonstop2h 29m
Chicago O'Hare Intl
Tue 1/13
8:56 am-12:07 pm
Nonstop2h 11m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Fri 1/9
2:10 pm-7:05 pm
1 stop5h 55m
Chicago Midway
Tue 1/13
5:30 pm-8:20 pm
Nonstop1h 50m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Sat 12/6
5:07 pm-6:36 pm
Nonstop2h 29m
Chicago O'Hare Intl
Mon 12/8
9:00 am-12:07 pm
Nonstop2h 07m
PhiladelphiaChicago
PHL - MDW
PHLMDW
Philadelphia
Wed 12/10
4:00 pm-5:10 pm
Nonstop2h 10m
Chicago Midway
Thu 12/11
6:05 pm-9:00 pm
Nonstop1h 55m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Wed 12/17
6:55 am-12:03 pm
1 stop6h 08m
Chicago O'Hare Intl
Thu 1/1
5:31 pm-12:27 am
1 stop5h 56m
PhiladelphiaChicago
PHL - ORD
PHLORD
Philadelphia
Wed 12/3
12:37 pm-6:43 pm
1 stop7h 06m
Chicago O'Hare Intl
Sat 12/6
6:45 am-1:19 pm
1 stop5h 34m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
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 83 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, November is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $44). Flying from Philadelphia to Chicago in July is currently the most expensive (average of $126). 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 44% on the cost of your flight, compared to a flight at noon.
Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from PHL to CHI are scheduled on a Monday (47 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Mike,Aug 2025
OKC - AUS
Boarding
Entertainment
Food
Overall
Comfort
Crew
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$60 | Average$172 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$185 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$277 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$323 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$166 | Average$320 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$168 | Average$308 | FlexibilityNo cancel fee | On-time71% |