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$52+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PHL
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$96
(Booking.com)

One-way from

$59
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$265

Good round-trip deal

$158 or less

Good one-way deal

$79 or less
Provider with most accurate pricing for Chicago (CHI)-Philadelphia flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Philadelphia flights.
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From Chicago (CHI) to Pennsylvania
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One-way flight from Chicago (CHI) to Pennsylvania
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Highest demand for flights based on searches. 32% potential increase in price ($102 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Pennsylvania.
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Price to beat on a one-way flight from Chicago (CHI) to Pennsylvania.
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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 April 15, 2025.

This Booking.com deal was found by Cheapflights users on 4/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/67:47 pmORD - LGA
1 stop13h 13mSpirit Airlines
Wed 5/77:59 pmLGA - ORD
1 stop13h 51mSpirit Airlines
Deal found 4/14$96
This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/219:08 pmORD - EWR
Nonstop2h 21mSpirit Airlines
Sun 5/255:55 amEWR - ORD
Nonstop2h 32mSpirit Airlines
Deal found 4/15$106
This JetBlue deal was found by Cheapflights users on 4/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/68:45 amORD - JFK
1 stop6h 42mJetBlue
Tue 5/68:00 pmJFK - ORD
Nonstop2h 54mJetBlue
Deal found 4/14$122
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:45 pmORD - LGA
Nonstop2h 18mDelta
Tue 5/278:55 pmLGA - ORD
Nonstop2h 46mDelta
Deal found 4/14$137
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 5/276:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 4/14$137
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:55 amORD - LGA
Nonstop2h 05mMultiple Airlines
Sun 5/410:50 pmLGA - ORD
1 stop9h 55mMultiple Airlines
Deal found 4/14$144
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2911:57 amORD - EWR
1 stop8h 08mMultiple Airlines
Wed 4/305:30 amEWR - ORD
Nonstop2h 33mMultiple Airlines
Deal found 4/14$148
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:18 pmORD - JFK
Nonstop2h 42mDelta
Sun 5/2511:00 amJFK - ORD
Nonstop2h 48mDelta
Deal found 4/14$153
This American Airlines deal was found by Cheapflights users on 4/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/105:40 pmORD - PHL
Nonstop2h 00mAmerican Airlines
Sun 5/115:00 amPHL - ORD
Nonstop2h 26mAmerican Airlines
Deal found 4/15$161
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Fri 5/168:26 pmORD - PHL
Nonstop2h 08mFrontier
Mon 5/195:01 pmPHL - ORD
Nonstop2h 28mFrontier
Deal found 4/14$162
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/175:25 pmMDW - EWR
1 stop4h 04mDelta
Sun 5/256:05 amEWR - MDW
1 stop8h 10mDelta
Deal found 4/13$168
This United Airlines deal was found by Cheapflights users on 4/13. 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.
Sat 5/246:13 pmORD - PHL
Nonstop2h 15mUnited Airlines
Tue 5/278:31 amPHL - ORD
Nonstop2h 24mUnited Airlines
Deal found 4/13$169

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 April 15, 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 5/6

7:47 pm-10:00 am

1 stop13h 13m

New York LaGuardia

Wed 5/7

7:59 pm-8:50 am

1 stop13h 51m

$96

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 5/21

9:08 pm-12:29 am

Nonstop2h 21m

Newark

Sun 5/25

5:55 am-7:27 am

Nonstop2h 32m

$106

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 5/6

8:45 am-4:27 pm

1 stop6h 42m

New York John F Kennedy Intl

Tue 5/6

8:00 pm-9:54 pm

Nonstop2h 54m

$122

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 5/24

5:45 pm-9:03 pm

Nonstop2h 18m

New York LaGuardia

Sun 5/25

6:59 pm-8:46 pm

Nonstop2h 47m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 5/27

6:10 am-7:30 am

Nonstop2h 20m

$137

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 4/30

5:55 am-9:00 am

Nonstop2h 05m

New York LaGuardia

Fri 5/2

6:30 am-12:03 pm

1 stop6h 33m

$144

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 4/29

11:57 am-9:05 pm

1 stop8h 08m

Newark

Wed 4/30

5:30 am-7:03 am

Nonstop2h 33m

$148

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 5/21

6:18 pm-10:00 pm

Nonstop2h 42m

New York John F Kennedy Intl

Sun 5/25

11:00 am-12:48 pm

Nonstop2h 48m

$153

ChicagoPhiladelphia

ORD - PHL

ORDPHL

Chicago O'Hare Intl

Sat 5/10

5:40 pm-8:40 pm

Nonstop2h 00m

Philadelphia

Sun 5/11

5:00 am-6:26 am

Nonstop2h 26m

$161

ChicagoWashington, D.C.

ORD - IAD

ORDIAD

Chicago O'Hare Intl

Fri 5/9

9:00 am-10:54 am

1 stop24h 54m

Washington, D.C. Dulles Intl

Sun 5/11

7:31 am-5:10 am

1 stop22h 39m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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, August is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $236). Flying from Chicago to Pennsylvania in March is currently the most expensive (average of $295). 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 April 15, 2025.

When flying from Chicago to Pennsylvania, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 April 15, 2025.

The most flights from CHI to USPA are scheduled on a Monday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Pennsylvania by month

Plan your trip to Pennsylvania by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Pennsylvania ranges from 2.7 - 4.4 inches per month. July is typically the wettest month, when rainfall can reach 4.4 in. February is typically the driest time to visit Pennsylvania when rainfall is around 2.7 in.

Temperature in Pennsylvania by month

Plan your trip to Pennsylvania by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Pennsylvania, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

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 April 15, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to Pennsylvania. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,876 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,876 reviews
Alaska Airlines
8.0
Very good
9,876 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,279 reviews
Alaska Airlines
8.0
Very good
9,876 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,876 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,876 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,658 reviews
Alaska Airlines
8.0
Very good
9,876 reviews

Overall

8.0

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 $59 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $69 and Delta 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 LaGuardia, Chicago O'Hare Intl - New York John F Kennedy Intl and Chicago O'Hare Intl - Newark.

  • 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 (81%), SWISS (77%), Alaska Airlines( 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 $938, our data indicates the cheapest price to be $88. The most popular route (Chicago O'Hare Intl - New York LaGuardia), is priced around $78.

  • 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, August is the cheapest month in which you can book a flight from Chicago to Pennsylvania (average of $236). Flying from Chicago to Pennsylvania in March is currently the most expensive (average of $295). 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 5 airlines flying from Chicago to Pennsylvania

Discover the top 5 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$52Average$108FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$333FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$103Average$301FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$125Average$298FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$136Average$368FlexibilityNo cancel feeOn-time69%

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