$47+ Cheap flights from Chicago (CHI) to Pennsylvania
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Jan 7 — Jan 141
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Pennsylvania
Cheapest flights from Chicago to PennsylvaniaExplore the most affordable flight options available from Chicago to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.
Explore the most affordable flight options available from Chicago to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.
This Trip.com deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:36 amORD - JFK
Nonstop2h 24mFrontier
Wed 12/171:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/7![Frontier logo]()
$78
This Priceline deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:36 amORD - JFK
Nonstop2h 24mFrontier
Mon 12/151:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/6![Frontier logo]()
$80
This Frontier deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:36 amORD - JFK
Nonstop2h 24mFrontier
Mon 12/151:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/6![Frontier logo]()
$81
This Cheapflightsfares deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Fri 1/167:30 amLGA - ORD
Nonstop2h 42mSpirit Airlines
Deal found 12/7![Spirit Airlines logo]()
$87
This Super.com deal was found by Cheapflights users on 12/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:36 amORD - JFK
Nonstop2h 24mFrontier
Fri 1/234:29 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/5![Frontier logo]()
$88
This Cheapflightsfares deal was found by Cheapflights users on 12/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/154:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Tue 12/168:41 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Deal found 12/8![Spirit Airlines logo]()
$94
This Frontier deal was found by Cheapflights users on 12/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:40 amORD - JFK
Nonstop2h 24mFrontier
Sat 1/101:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/8![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Deal found 12/7![Spirit Airlines logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Tue 12/168:41 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Deal found 12/7![Spirit Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 12/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/1811:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/8![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:44 amMDW - EWR
Nonstop2h 01mFrontier
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Deal found 12/7![Frontier logo]()
$104
This Priceline deal was found by Cheapflights users on 12/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:36 amORD - JFK
Nonstop2h 24mFrontier
Sat 1/241:00 pmJFK - ORD
1 stop10h 44mFrontier
Deal found 12/5![Frontier logo]()
$104
Find flight deals from Chicago to Pennsylvania
Keep the following information in mind while searching for Chicago to Pennsylvania flight deals. Data was last updated December 8, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $77 (Kiwi.com) |
One-way from | $47 (Kiwi.com) |
Popular in | March |
Cheapest in | October |
Average price | $251 |
Good round-trip deal | $209 or less |
Good one-way deal | $119 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Pennsylvania that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Chicago to Pennsylvania that are best for you.
Fly from
Chicago
Fly to
Pennsylvania
Route
Depart
Return
Price
ChicagoNew York
MDW - JFK
MDWJFK
Chicago Midway
Wed 1/21
1:20 pm-12:43 am
1 stop10h 23m
New York John F Kennedy Intl
Wed 1/28
6:10 am-12:05 pm
1 stop6h 55m
$128
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Fri 1/16
6:00 am-9:08 am
Nonstop2h 08m
New York LaGuardia
Sun 1/18
5:15 pm-6:55 pm
Nonstop2h 40m
$139
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Thu 1/8
12:15 pm-3:40 pm
Nonstop2h 25m
New York LaGuardia
Sun 1/11
6:50 pm-8:47 pm
Nonstop2h 57m
$139
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Fri 2/6
6:05 pm-9:10 pm
Nonstop2h 05m
New York LaGuardia
Mon 2/9
6:30 pm-8:05 pm
Nonstop2h 35m
$139
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Sat 2/7
8:45 am-12:02 pm
Nonstop2h 17m
New York John F Kennedy Intl
Sat 2/14
9:15 pm-11:10 pm
Nonstop2h 55m
$139
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Thu 1/29
6:00 am-9:26 am
Nonstop2h 26m
New York LaGuardia
Mon 2/2
4:30 pm-6:28 pm
Nonstop2h 58m
$139
ChicagoPhiladelphia
ORD - PHL
ORDPHL
Chicago O'Hare Intl
Thu 1/1
11:00 am-2:11 pm
Nonstop2h 11m
Philadelphia
Tue 1/6
1:10 pm-2:40 pm
Nonstop2h 30m
$139
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Fri 1/30
6:00 am-9:26 am
Nonstop2h 26m
New York LaGuardia
Fri 1/30
4:30 pm-6:28 pm
Nonstop2h 58m
$139
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Tue 1/20
10:52 am-2:08 pm
Nonstop2h 16m
Newark
Tue 1/20
6:27 pm-8:13 pm
Nonstop2h 46m
$139
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Wed 1/28
10:29 am-1:54 pm
Nonstop2h 25m
New York John F Kennedy Intl
Wed 2/11
7:35 pm-9:35 pm
Nonstop3h 00m
$139
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Pennsylvania
Have a flexible travel schedule? Discover the best time to fly to Pennsylvania from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Pennsylvania
What is the cheapest month to book a flight from Chicago to Pennsylvania?
Currently, November is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $67). Flying from Chicago to Pennsylvania in July is currently the most expensive (average of $139). 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.
What is the cheapest time of day to fly from CHI to PA?
Find hourly flight availability from Chicago to Pennsylvania. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 8, 2025.
One of the essential ways to save on airfare from Chicago to Pennsylvania is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 26% on airfare.
What is the cheapest day to fly from Chicago to Pennsylvania?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Pennsylvania. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago to Pennsylvania flight should consider departing on Friday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Pennsylvania
Explore weekly flight availability from Chicago to Pennsylvania. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 8, 2025.
The most flights from CHI to USPA are scheduled on a Friday (45 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Chicago to Pennsylvania?
Reviews of airlines servicing Pennsylvania
Get insights into the airlines that provide service to Pennsylvania. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pennsylvania. Reviews last updated December 8, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Pennsylvania have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Pennsylvania. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Pennsylvania
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Chicago to Pennsylvania
Discover the top 6 airlines that operate flights from Chicago to Pennsylvania. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$63 | Average$260 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$78 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$100 | Average$340 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$103 | Average$304 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$111 | Average$363 | FlexibilityNo cancel fee | On-time69% |