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$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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Chicago to Pennsylvania

Cheapest flights from Chicago to Pennsylvania
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 23, 2025.

This Trip.com deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:40 amORD - JFK
Nonstop2h 24mFrontier
Mon 2/24:29 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/22$86
This CheapOair deal was found by Cheapflights users on 12/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:40 amORD - JFK
Nonstop2h 24mFrontier
Mon 1/511:00 amJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/23$119
This Expedia deal was found by Cheapflights users on 12/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - PHL
Nonstop2h 15mFrontier
Mon 1/53:40 pmPHL - ORD
1 stop20h 09mFrontier
Deal found 12/22$120
This Super.com deal was found by Cheapflights users on 12/22. 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 12/316:40 amORD - JFK
Nonstop2h 24mFrontier
Sat 1/311:00 amJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/22$121
This Mytrip deal was found by Cheapflights users on 12/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amORD - LGA
1 stop14h 00mMultiple Airlines
Mon 2/27:30 amLGA - ORD
Nonstop2h 42mMultiple Airlines
Deal found 12/22$130
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:15 pmORD - PHL
Nonstop2h 16mUnited Airlines
Thu 1/16:35 amPHL - ORD
Nonstop2h 28mUnited Airlines
Deal found 12/22$139
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:10 pmORD - EWR
Nonstop2h 16mUnited Airlines
Thu 1/17:59 amEWR - ORD
Nonstop2h 55mUnited Airlines
Deal found 12/22$139
This WAYA deal was found by Cheapflights users on 12/22. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - PHL
Nonstop2h 15mMultiple Airlines
Thu 1/16:00 amPHL - ORD
1 stop5h 40mMultiple Airlines
Deal found 12/22$141
This Trip.com deal was found by Cheapflights users on 12/22. 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.
Wed 12/317:00 amORD - LGA
1 stop14h 00mMultiple Airlines
Tue 1/68:37 pmLGA - ORD
Nonstop2h 30mMultiple Airlines
Deal found 12/22$143
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/316:40 amORD - JFK
Nonstop2h 24mFrontier
Wed 1/71:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/21$147
This Cheapflightsfares deal was found by Cheapflights users on 12/21. 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 12/313:26 pmORD - EWR
1 stop7h 33mSpirit Airlines
Wed 1/76:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Deal found 12/21$153
This Cheapflightsfares deal was found by Cheapflights users on 12/22. 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.
Tue 12/309:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Thu 1/16:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Deal found 12/22$154

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 23, 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

$256

Good round-trip deal

$180 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
Search Deals
From Chicago (CHI) to Pennsylvania
Search Deals
One-way flight from Chicago (CHI) to Pennsylvania
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Pennsylvania.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Pennsylvania.
Search Deals

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 23, 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

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 2/20

5:58 pm-8:59 pm

Nonstop2h 01m

New York LaGuardia

Sun 2/22

7:40 am-9:22 am

Nonstop2h 42m

$116

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 12/31

2:15 pm-5:30 pm

Nonstop2h 15m

Philadelphia

Mon 1/5

3:40 pm-10:49 am

1 stop20h 09m

$120

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 5/27

5:15 am-7:00 pm

1 stop12h 45m

New York LaGuardia

Sat 5/30

8:00 am-7:48 pm

1 stop12h 48m

$124

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 1/30

10:48 am-5:58 pm

1 stop6h 10m

New York LaGuardia

Fri 1/30

8:39 pm-8:18 am

1 stop12h 39m

$124

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 1/30

7:10 am-10:41 am

Nonstop2h 31m

New York LaGuardia

Mon 2/2

6:50 pm-8:47 pm

Nonstop2h 57m

$139

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 2/25

8:00 am-11:09 am

Nonstop2h 09m

New York LaGuardia

Sat 2/28

6:10 am-7:55 am

Nonstop2h 45m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 2/6

8:00 pm-11:00 pm

Nonstop2h 00m

New York LaGuardia

Sun 2/8

9:45 pm-11:15 pm

Nonstop2h 30m

$139

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 1/21

9:40 am-12:56 pm

Nonstop2h 16m

New York John F Kennedy Intl

Sat 1/24

5:25 pm-7:36 pm

Nonstop3h 11m

$139

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Wed 12/31

6:15 pm-9:31 pm

Nonstop2h 16m

Philadelphia

Thu 1/1

6:35 am-8:03 am

Nonstop2h 28m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 2/3

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Wed 2/11

6:00 am-7:40 am

Nonstop2h 40m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 60 results
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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 23, 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. Sunday evenings 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 23, 2025.

The most flights from CHI to USPA are scheduled on a Tuesday (44 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (19 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 23, 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.
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,075 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago to Pennsylvania?

    For as low as $116, Spirit Airlines can have you in Pennsylvania from Chicago in 2h 01m. There are 731 mi between Chicago and Pennsylvania. Most flights are nonstop.

  • What are the cheapest airlines to fly from Chicago to Pennsylvania one-way?

    One-way options have recently been found by users for as low as $48 on American Airlines. Other airlines that offer cheap prices include Frontier from $49 and Southwest from $63 one-way.

  • What are the most popular routes from Chicago to Pennsylvania?

    The most popular flight routes from Chicago to Pennsylvania are Chicago O'Hare Intl - New York John F Kennedy Intl, Chicago O'Hare Intl - Newark and Chicago O'Hare Intl - New York LaGuardia.

  • What are the most reliable airlines from Chicago to Pennsylvania?

    Before booking your flight to Pennsylvania from Chicago, check out the most reliable airlines to get you to your destination on time: Air Canada (86%), Malaysia Airlines (79%), Cathay Pacific( 76%).

  • What are the cheapest flights from Chicago to Pennsylvania?

    Looking for the cheapest flight from Chicago to Pennsylvania? While on average our users pay $730, our data indicates the cheapest price to be $40. The most popular route (Chicago O'Hare Intl - New York John F Kennedy Intl), is priced around $58.

  • Can I find deals for flights from Chicago to Pennsylvania that include hotel bookings?

    Yes. In addition to deals on Chicago to Pennsylvania flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Pennsylvania?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Pennsylvania.

  • Can I find deals for business class flights from Chicago to Pennsylvania?

    Yes. Cheapflights offers flight deals from Chicago to Pennsylvania by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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.

See more FAQs

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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.
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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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$260FlexibilityNo cancel feeOn-time65%
FrontierCheapest$67Average$166FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$99Average$340FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$103Average$299FlexibilityNo cancel feeOn-time63%
DeltaCheapest$108Average$477FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$109Average$357FlexibilityNo cancel feeOn-time69%

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