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$62+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Find 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 October 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 11/115:10 amORD - LGA
1 stop9h 49mSpirit Airlines
Tue 11/114:59 pmLGA - ORD
Nonstop2h 35mSpirit Airlines
Deal found 10/16$98
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Thu 11/66:40 amORD - JFK
Nonstop2h 23mFrontier
Tue 11/111:00 pmJFK - ORD
1 stop12h 59mFrontier
Deal found 10/16$98
This Priceline deal was found by Cheapflights users on 10/16. 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.
Sat 11/227:21 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Mon 11/2412:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Deal found 10/16$99
This Priceline deal was found by Cheapflights users on 10/16. 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.
Tue 10/286:40 amORD - JFK
Nonstop2h 23mFrontier
Fri 10/3111:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 10/16$99
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 10/286:00 amORD - LGA
1 stop13h 00mSpirit Airlines
Fri 10/316:04 pmLGA - ORD
1 stop7h 59mSpirit Airlines
Deal found 10/14$100
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Tue 10/2812:37 pmORD - JFK
1 stop10h 56mFrontier
Tue 11/411:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 10/14$100
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 11/103:26 pmORD - LGA
1 stop6h 55mSpirit Airlines
Sat 11/158:59 amLGA - ORD
Nonstop2h 31mSpirit Airlines
Deal found 10/16$101
This Priceline deal was found by Cheapflights users on 10/16. 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.
Fri 10/316:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 11/311:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 10/16$101
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 12/33:53 pmORD - LGA
Nonstop2h 07mSpirit Airlines
Mon 12/87:56 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Deal found 10/15$102
This Priceline deal was found by Cheapflights users on 10/16. 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 11/106:40 amORD - JFK
Nonstop2h 23mFrontier
Tue 11/1111:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 10/16$102
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 12/310:59 amORD - LGA
Nonstop2h 05mSpirit Airlines
Sun 12/77:56 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Deal found 10/15$103
This Priceline deal was found by Cheapflights users on 10/15. 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.
Thu 11/136:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 11/1711:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 10/15$103

Cheap flight deals from Chicago to Pennsylvania

Keep the following information in mind while searching for Chicago to Pennsylvania flight deals. Data was last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Cheapflightsfares)

One-way from

$62
(Priceline)

Popular in

March

Cheapest in

October

Average price

$196

Good round-trip deal

$125 or less

Good one-way deal

$50 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 ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 16, 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

Tue 10/28

6:00 pm-9:07 pm

Nonstop2h 07m

New York LaGuardia

Wed 10/29

8:15 am-9:55 am

Nonstop2h 40m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/4

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 11/5

9:10 am-10:40 am

Nonstop2h 30m

$137

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 11/4

11:00 am-2:11 pm

Nonstop2h 11m

New York LaGuardia

Tue 11/11

6:15 pm-7:57 pm

Nonstop2h 42m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/12

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Wed 11/19

9:10 am-10:40 am

Nonstop2h 30m

$137

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 10/24

8:00 pm-11:24 pm

Nonstop2h 24m

New York LaGuardia

Fri 10/31

6:15 pm-7:57 pm

Nonstop2h 42m

$138

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 11/10

8:25 pm-11:25 pm

Nonstop2h 00m

New York LaGuardia

Fri 11/14

9:55 pm-11:20 pm

Nonstop2h 25m

$138

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 11/6

6:30 pm-9:46 pm

Nonstop2h 16m

New York LaGuardia

Sun 11/9

6:15 am-7:57 am

Nonstop2h 42m

$138

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Fri 10/31

6:25 pm-9:48 pm

Nonstop2h 23m

Newark

Sun 11/2

9:59 pm-11:34 pm

Nonstop2h 35m

$138

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 10/29

11:02 am-2:15 pm

Nonstop2h 13m

Newark

Sun 11/2

7:18 am-9:05 am

Nonstop2h 47m

$138

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 12/17

7:00 am-10:17 am

Nonstop2h 17m

New York John F Kennedy Intl

Mon 1/19

5:30 pm-7:45 pm

Nonstop3h 15m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

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 October 16, 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 30% 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 October 16, 2025.

The most flights from CHI to USPA are scheduled on a Thursday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 October 16, 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
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,982 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,043 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,097 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,137 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $137, United Airlines can have you in Pennsylvania from Chicago in 2h 05m. There are 722 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 $68 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $69 and Southwest from $69 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: United Airlines (86%), Air New Zealand (80%), Air Canada( 78%).

  • What are the cheapest flights from Chicago to Pennsylvania?

    Looking for the cheapest flight from Chicago to Pennsylvania? While on average our users pay $572, our data indicates the cheapest price to be $69. The most popular route (Chicago O'Hare Intl - New York John F Kennedy Intl), is priced around $54.

  • 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.
O'Hare Intl to John F Kennedy Intl flights
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O'Hare Intl to Charlotte flights
Midway to Dulles Intl flights
St. Louis to John F Kennedy Intl flights

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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$260FlexibilityNo cancel feeOn-time65%
FrontierCheapest$67Average$168FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$103Average$304FlexibilityNo cancel feeOn-time63%
DeltaCheapest$108Average$477FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$109Average$290FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$384FlexibilityNo cancel feeOn-time69%

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